Showing posts with label #chemise. Show all posts
Showing posts with label #chemise. Show all posts

Thursday, January 26, 2023

Special Wednesday

My lady and I had a great day yesterday.  We were both off from work, and so we slept in (relatively speaking) and enjoyed our coffee together. Next, we got ourselves down to the basement for a workout (bike for her, treadmill for me), followed by showering, which left us refreshed and ready for love-making.

I dressed in a purple bralette and panty set, covered by a purple chemise. I was also locked as usual in my 3D printed cage, which is the most comfortable one I own. She wore a somewhat matching bra and panty set, except hers accentuated rather than covered her breasts. She looked magnificent. 

She asked how we're doing on the orgasm ratio, and I told her that we were just barely above 3:1, pretty well below the target of 5:1 that she set, but I reminded her that the goals are there for me to follow and for her to change or deviate from whenever she feels like it. There's not much point in being the dominant partner if you can't just change the rules on a whim, is there?  

We next enjoyed a lengthy session of pussy worship. Methinks I could do that for hours. She unlocked me and proceeded to suck my cock; something she rather loves doing and I would not dream of denying her that pleasure, notwithstanding how much I enjoy it as well. I've mentioned previously that I'm above average in size, about 20 cm (8 in) in length and proportionally thick. My lady has determined that she enjoys taking me all the way into her throat, which is simply amazing on multiple fronts. She gets turned on from doing that, particularly when I am playing with her nipples at the same time. It is the most incredible feeling. She also rode me for a while, and then whispered in my ear that she was going to fuck me.

And so she did. We moved up to a realistic cock that is just marginally shorter than mine, and also slightly less thick. It has an advantage over the pink one we've been using because, even though it's bigger, it is more flexible. She entered me easily after some fingering, and lots of lube. They tell you that anal play requires lots of lube. I can confirm that it makes all the difference. It was easily the most enjoyable fuck she's given me.  While she did so, I sucked on Carl (our large black dildo) and  masturbated. My lady had a vibrating butt plug in her ass, and somehow managed to lodge another dildo in her pussy, held in place by the strap-on harness. We basically had all of our holes filled, except her mouth, which she took advantage of to say lots of dirty things!  

The situation got me fantasizing about Carl being a real guy, inviting us to his place for a party, only to discover that my lady and I were the entertainment for him and several of his friends, which made me rock hard. (Maybe I'll detail out that fantasy in an upcoming post). My lady gave me permission to cum, and so I did. She used my semen to lubricate her clitoris, and came shortly after I did. We cuddled for a while, and just enjoyed being together.

We had lunch, took naps, did some housekeeping, made dinner together, ate, watched some TV and then retired for the night. It was a great day, as I said in the beginning. I love my wife and I love our life. I am a very fortunate person.

Thanks for reading.

Jennifer

Wednesday, July 7, 2021

Awesome

My lady is awesome. I love her more deeply than I previously understood possible. 

I will recount some of the things I love about her, but inevitably I will neglect some important facet, because there are more aspects to her magnificence than my mind can retain at any given time.  Let me offer a short story about her.

As near as I can tell, my lady never really had a male figure in her life who treated her well.  I shall not recount the details, but neither her father, nor her ex-husbands gave her the respect and love that she deserves. Her exes had issues. I'll leave it at that. Still, she was able to separate their shortcomings from her own image of self-worth to a large degree. She is intelligent, ethical and strong. Not to mention beautiful, funny and so very sexy.

In spite of all that has been thrown her way, and yes, the choices she has made that didn't work out, my lady has been steadfast in her values. Her moral compass has never drifted. She tolerated unacceptable behavior, but only until she reached the decision that there was no longer the possibility of favorable resolution. She raised wonderful children without the support of a good husband, and for that alone she deserves a Medal of Honor.

You might imagine that, having had that history with men, when we started seeing each other her signal flares might have gone off. Danger, danger, Will Robinson... I disclosed as early as I could reasonably do so the "fatal flaws" that I felt that I carried, namely:

  • Divorced
  • Had an affair
  • Crossdresser

I have made many mistakes in my life. I shall not be defined by them. I have learned from them, and have grown substantially as a human as a result of them. Among my my mistakes was marrying a young lady (when I was a young man) with whom I could not communicate and from whom I grew apart. Having an affair was another one - a big one. I rationalized it, of course, but there's no defending it.  All I can to is own up to it, learn from it and move on. 

So, yeah, that's not a list of attributes a lady looks for in her man. It screams, "run for the hills!!!"  Particularly after the prior experiences she's had. It reminds me of this exchange in "As Good As It Gets" 

            CAROL

Why can't I have a normal boyfriend??? Why? Just a regular boyfriend who doesn't go nuts on me... 

BEVERLY
(butting in)
Everybody wants that, dear -- it doesn't exist...

That's definitely how I have felt - not normal. And I'm quite aware that I'm No. 3 of 3 in that regard in terms of the men who've lined up for her affections.

Except for two things. First, I love and respect her immeasurably. That makes me different than her prior men. Second, my lady makes me feel normal. Actually, she makes me feel exceptional. She makes me feel justified being who I am, how I am, and what I am. She sees the goodness in me (yes, I have good traits, too). She loves me for those traits, and she is learning to accept, and, dare I say, embrace my other "non-traditional" characteristics.

These past weekend was a long and glorious one. I had painted my toenails during the week, and as the weekend approached, chose not to remove the polish. My lady has been aware of my penchant for this, and has seen the evidence; I don't always do a great job removing all remnants. I left my socks on when she arrived, and explained why, emphasizing that I didn't want to push her out of her comfort zone. She smiled and said that she wanted to see them, so off came the socks and another step was taken. She complimented me on the job I did and said I looked sexy. What an amazing woman. Have I said that already?

We had a lot of sex this weekend. I cannot recount the events in sequence or in full detail. Frankly, I was too caught up in being with her to spend time committing it all to memory or writing it down. I remember vignettes, and I definitely remember feelings. I spent quite a bit of time, to my extreme pleasure, worshipping her pussy. I love everything about it, the taste, the feeling, the aroma, and most of all, how it makes her feel. I'm good at it, this I know. I told her that I'd love for her to grab hold of my head and just rub her pussy all over my face, using me to climax, and leaving my face a wet, hot mess that I'd leave unwashed for the rest of the day. We did that. Actually, I got a bit eager and did some of the moving myself. This surprised her, and she released maybe a half cup of pee into my mouth and onto my face, drenching me. It was warm and salty and I loved it. She didn't know that she'd done it until I told her. She was embarrassed and apologetic, until she saw how absolutely rock hard my cock had become. I wore her scent for hours. I could smell her and feel her on my skin after it dried. I felt possessed by her, marked and defined as hers, and I reveled in the feeling. I can't wait to repeat it.

She told me that I wasn't allowed to cum on Saturday, that she was going to tease me and then on Sunday she was going to fuck me with her purple strapless dildo. She had come maybe three times by this point in the weekend, and I was clearing the seven day mark since my last orgasm. I wore the cage a lot, including at a party we went to later.  However, being with her, or even thinking of her when we were apart kept me engorged, and I was a bit concerned about continued confinement in that condition, so I freed myself later that evening. A damaged penis is not good for either of us. 

On Sunday morning, we had a cuddle session that turned X-rated. She rode my cock and I worshipped her pussy.  She whispered how she was going to fuck me and make me hers. I fell deeper into sub-space, and begged her to take me in that way.  For the afternoon session, I spent time preparing myself to be the recipient. I still don't have the best procedure, I think, but I was successful in ensuring that I was clean back there. I went to her room (soon to be our room) while she tended to other things. I secured the restraints to my limbs, and my legs and right arm to the bed straps. When she came into the room, I was wearing a chemise, bunched up to my stomach, slowly masturbating with my free hand, and my cock was rock hard. This turned her on quite a bit. She likes watching me masturbate, and having her watch me is a real turn-on. 

As I believe I've mentioned previously, I have a pretty large cock. It measures between 7.5 and 8.0 inches and is proportionally thick. That is unusual in the general population, from the research I've done, and anecdotally even more rare among submissive, crossdressing males. My lady loves my cock, and the feeling is mutual. She loves to suck it, kiss it and tease it. I love watching her, and the feeling of her mouth on my cock is wonderful. We both love when I'm inside her. This is one of the many ways that we fit perfectly together. My lady had her way with me in these regards, and then she released my leg restraints to gain access to my rear opening. Some tongue action, followed by a lubricated finger got me ready. She started with the pink strap-on, which is a bit smaller. My back door has some work to do in order to accommodate larger objects, but we're working towards that. She had me suck her pink cock for a while before getting into position. I think we both like when she watches me do that. I looked at the combined scene and was struck by how unusual and incredibly erotic it was. My chemise, her beautiful, naked, sexy body poised to mount me, the strap-on harness, the pink dildo, my shaved legs, the restraints on my ankles, and my painted toenails. She entered me carefully, giving me time to adjust to the invader. She started moving in me, and we kissed. I looked into her smoky, eyes and was lost in her beauty.

After loosening me up, she switched over to the strapless one. It's going to take some practice to get the technique down so that it gives her the pleasure we seek for her while she fucks me. We stopped after a while, but made good progress. I want for us both to be able to orgasm when she fucks me. I long for the time when we're living together and she'll say, out of the blue, "go get yourself ready, I'm going to fuck you."  Ooooh.  

She did orgasm, using a combination of my mouth, my cock and her nimble fingers. It was a good one, based on my eye-witness account. She decided that she wanted me to come, and I ended up masturbating while she watched.

On Monday, we had more quality time in the morning as a prelude to a more intimate afternoon session. I had suggested that we spend part of the day taking a hike. To be honest, I was looking forward to that as a highlight of the day. I love being with her in all places, and doing all things. As it turned out, after taking care of things at our respective houses, when I returned to her place, my lady announced that we would not be hiking that day. Initially, I was crestfallen. She explained the timeline we had for the remaining part of the day, and determined that there wasn't time for the hike. I didn't argue, but I did express that I was a little disappointed. There are a few takeaways from this interaction. First, I quickly realized that if I truly meant what I said to her numerous times, i.e. "I'll do anything for you," then that includes abiding by her decision when it's not up for debate. This was one of those cases, and I took comfort in being able to follow her lead without drama. Second, it was really hot outside, so a hike at that time of day would have been somewhat miserable. I was happy that she made the decision and that I accepted it. That would have been true even if it had turned out that we did have time. But she was correct. By the time we did the other necessary things, we'd have been left with the choice of a hike or time in the bedroom. Duh.

Our bedroom time focus was on anal again, but this time she was the recipient. She likes it a lot, and we will be doing more of that. I followed her pattern from the day before, staring with my tongue, then my fingers and finally the pink dildo in the strap-on. She's not ready to accommodate my cock, yet. She wanted to repeat the double penetration scene we did once, but I'm having trouble keeping my cock hard and ready to play in that situation. We used the realistic cock as the second player for her pussy, and she came quite hard that way. We closed out the session with her stroking me for a good long while, until her arm got tired. I loved how it felt, and she's learning how to work me, but we have some more practicing to do. I took over for her, and she whispered into my ear. When she told me how she's going to fuck me regularly, I climaxed intensely. She smiled.

I love this woman, more than words can express.

Thanks for reading.

Jen

Monday, June 7, 2021

A Weekend Away

We had a wedding to attend this past weekend about 90 minutes away. We could have driven there on Saturday and back the same night, but decided to make a weekend out of it. We rented a nice secluded Airbnb near the water. As we both had busy workdays on Friday, we didn't arrive until after seven. I had asked for instructions, and she decided that I should be locked in the black Kink3D cage for the ride down. I gave her both keys. 

We had a quiet dinner in the cottage, along with what turned out to be too many glasses of wine. We cleaned up and made for the bedroom. Some wonderful caressing and kissing led to more intimate acts. She unlocked me but removed only the cage; the ring acted to partially restrict blood flow, making my cock more rigid and veiny. She played with me for a while, sucking and licking my cock. It feels so nice, and I know how she loves to do that. Win win. Soon I returned the favor. I found my happy place, between my lady's thighs, and provided oral homage. Alas, the effects of the wine were such that she found it all too stimulating too quickly. I removed the ring after calming down for a bit, and we slept together.

In the morning, we both wore animal prints, her in a satin pajama top and nothing else, me in a chemise and panties. We had coffee on the screened-in patio and then she made us breakfast, which of course was delicious. Among her many talents is the ability to turn even a simple meal into a work of art for the taste buds. 

We decided it was time for more horizontal activities, so there we went after a quick shower. She teased me and soon I was begging to lick her pussy. She tasted herself on her fingers, denying me the pleasure. She then grabbed her favorite dildo, the one that looks like mine (we have to give this one a name so it'll be easier to refer to it). She knelt over me and sucked it while I lay there watching. It's such a turn-on watching her do that. Then she started fucking herself with it, and I masturbated while watching her. She pulled it out and tasted herself on it, eliciting a spontaneous moan that I realized was coming from me. Reinserting it, she got it wet with her juices and offered it to me. I sucked the cock while looking at her, tasting the delicious wetness she imparted to it. I don't know what she was thinking, but it felt so naughty doing that while looking directly into her eyes. 

She put our friend aside and we got into a sixty-nine. It's important to me that my lady come first. There are several reasons, most of all because "ladies first" is still a thing as far as I'm concerned. I think I written about several of the other reasons before. Come she did, on my face, with my tongue and lips worshipping her the way she deserves it. It is glorious to watch her spasm and hear her climax. We switched to missionary after that. While she's too sensitive for oral stimulation after a climax, my lady enjoys penetration, and of course so do I. I asked if she wanted me to come this day or wait until the next. She wanted me to climax, and so not long after her decision I let loose a large (for me) flow of semen. I've come not more than once per week for a while now, and I can definitely say that when I do they are more intense and rewarding. After cuddling a while, we got up and dressed.

We tooled around the nearby town and shopped a little. It was fun looking at ladies' clothing together. I'm not sure if we were browsing for her, me, or us. The selections were limited however, and the prices steep so we didn't buy anything. We had a light lunch and napped. She asked me to wash her back for her, so we entered the bathroom. We didn't make it all the way into the shower before some serious foreplay started. A lot of teasing, sucking and licking, but then we got ourselves together and got on with the shower and getting ready to go.

The wedding was beautiful, and we had a grand time. There were lots of beautiful people all dressed up beautifully. I found myself taking notice of the dresses and shoes the ladies wore. You have to anticipate the conditions before you choose your footwear, you know. It was an outdoor wedding so, no stiletto heels were to be found. I was so proud to have been her "arm candy" as she called me. There is never a place I'd rather be than at her side. I took it upon myself to fetch her drinks for her; the gentlemanly thing to do, I think, but also the wedding connection was through her friends and I wanted to be sure she had lots of time with them. I also flat out enjoy serving her, so there was no downside in my view.

We stayed a good long while, chatting, drinking (moderately) and dancing. I drove us the short distance back to our place. We crashed out. Alas, I awoke at 2:00 and could not go back to sleep. My lady slept better, but my lack of sleep ruined any morning opportunities we might have otherwise had. We checked out and returned home, took care of things and I came over to her place later. We had planned to have another love-making session, but I was still in a funk, so we ended up just having dinner and not long after, I went home and went to bed.

Lack of sleep definitely impeded my sex drive, but I got to wondering if my having climaxed the day before didn't also contribute to it. My lady loves when I orgasm. I do, too. Still, I wonder if we might be better off if my climaxes are delayed until the end of the weekend, or even skipped now and again. I like the tease and denial, the anticipation, and the uncertainty. Most of all, I like to please my lady, and I want to always be on my best game to do that. That means getting enough sleep, at least. The rest is something we'll have to discuss, and see what she's comfortable with.

Thanks for reading.

Jen

Wednesday, June 2, 2021

A Memorable Weekend

I'm afraid I waited a bit long to write about the rest of our weekend, so some of what I'm going to say might be inaccurate, but I'll do the best I can. Specific details might be juxtaposed or flat-out wrong, but the feeling is not lost. Being in her presence fills me with happiness beyond words.

On Sunday, we had a bit of a recovery day. She came to my place and brought breakfast. We did some decluttering to help me get closer to moving in with her, dropped off some clothes at a charity collection place, did some shopping, had lunch, and generally hung out all day.  I was locked in my new Kink3D device. In the late afternoon, I worshipped her pussy and she had a satisfying orgasm.  She told me I wasn't allowed to come this day, which was a turn-on. We dined, and I spent the night with her, unlocked. 

I brought pajamas and a robe to wear in the morning. I'm trying not to push my crossdressing; it's far less important to me than she is, and her comfort takes precedence. She has been supporting of me, even directing me to wear a chemise during love-making, and she tells me I look hot. Not nearly as hot as she, but I greatly appreciate the compliments. One evening this weekend, we wore matching style chemises of mine; she chose the pink one and I wore black (the one she'd worn the night before). That was fun.

On Monday, we awoke and cuddled in bed. There's no better way to start a day than embracing the one you love. Things heated up and soon she was riding my cock, and oh that felt so nice. She orgasmed that way, with a little help from her fingers on her clitoris, and mine on her nipples. She didn't want me to go down on her, which I totally understand. We're both super conscious of being clean and smelling nice. At the same time, I get really turned on by her womanly aroma and taste when the opportunity to worship her occurs not immediately after she showers. Maybe that's a boundary that is somewhat movable. I went home to tend to some things, and she did likewise. We had some family obligations in the mid-afternoon, and then went to my place after, in separate cars. I prepared things while awaiting her arrival.  

She had several specific instructions. I asked if I should be locked or unlocked.  "Locked," she said with authority and without hesitation. That caused some swelling. I also arranged a camera on a tripod and some mirrors. The camera was screencast to the bedroom TV. She wanted to watch the action from different angles. I obviously didn't hit "record." I wondered if that was something she'd want. In one sense, that could be fun, but the risk of later accidental exposure is something to consider seriously.

When she arrived, I was in bed, three limbs secured to the straps, wearing a red chemise and my black cage. All the toys were clean and ready. She came in, attached my free arm and disrobed, revealing a sexy black lace teddy enshrouding her gorgeous, womanly body. Things were getting pretty tight down there by this point.

She teased me, playing with my caged cock, pinching and biting my nipples, making me beg to worship her pussy, and giving me just the briefest taste now and again. I'm thinking that physical addiction to pussy might be a thing, because in addition to loving her so, I absolutely yearn for her taste. She touched herself, and placed her sticky delicious fingers in my mouth. So hot. She used the seven inch cock that looks like mine, rubbing it all over her pussy. I watched her taste it. Then she fucked herself with it while I stared, in awe. She pulled it out and offered the cock to me. I sucked it hungrily, tasting her sweetness. 

Eventually she untied and uncaged me, as she had other plans. I donned the strap-on with the pink dildo. With her on all fours, I lubricated her rear channel, and penetrated her. The intent was for my cock to penetrate her pussy at the same time, but it wasn't cooperating. Despite being really turned on by the whole scene, I couldn't get things going on my end. She improvised, rubbing my semi-erect cock against her clitoris while I fucked her ass. She sucked on the seven inch cock, while we watched ourselves on the TV. I was really hot, and she came furiously. We cuddled for a bit, and I started fondling myself. She told me she likes to watch me do that. With her encouragement, I got harder. 

She wanted me to come, so we decided to try the missionary position. She whispered how this was my chance to come, because afterward she was going to lock me up for the week. That definitely made me harder. I whispered that once we're married and under the same roof that I want her to have all the keys to my devices. I sensed a climax inbound, and it definitely felt like I was coming. My cock also rather quickly deflated. However, I didn't actually cum. No semen came out. It was odd, but not unsatisfying. While she watched, I inserted two fingers into her pussy to check.  I pulled them out and tasted them. All her, no me. Hmmm. It's ok, because it did feel like a climax. I just fired a blank round for some reason. 

The rest of the evening was spent over dinner and relaxing in front of the TV. Every day that I spend with her, I love her more. She is my world, my everything. 

Thanks for reading.

Jen


Sunday, May 30, 2021

Love is Real

Love

Love is real, real is love
Love is feeling, feeling love
Love is wanting to be loved

Love is touch, touch is love
Love is reaching, reaching love
Love is asking to be loved

Love is you, you and me
Love is knowing we can be

Love is free, free is love
Love is living, living love
Love is needing to be loved

                    - John Lennon

I've known those lyrics for decades, but I never understood them until I fell in love with my lady. I never knew it was possible to love someone so deeply and completely. I thought it was just words by an amazing songwriter. Now, I know better.

Since this is a sex blog, that's what I'm going to focus on in this posting. However, the reader should know that this is representative of but one facet of the shimmering diamond that is our love.

We spent Friday afternoon together, going to a beautiful nearby garden before the rainy weekend started. We visited that garden early in our relationship, and ended the evening making love for the first time, so it has a special meaning for us. This day, after our visit we made love again. Passionate, intense, naked love that was extremely gratifying for both of us. It had been over four days for her, which is a long time for her to go without an orgasm. For me, the counter had reached twelve days. It had been a busy week that kept us both exhausted, and last week you'll recall that I didn't have an orgasm. Oddly, towards the end of the week, my sex drive seemed to wane. It was like 'the boys' had given up trying, and I wasn't feeling a strong urge. 

That changed rather quickly when we disrobed and climbed into my bed. The merest touch of her hands on my skin was enough to set off a DEFCON 1 alert, and within seconds I was ready to launch.  We kissed and stroked, I suckled her magnificent breasts and she tenderly bit and sucked on my nipples, which I love. She spent quite a bit of time orally tending to my cock. It felt fabulous. I have difficulty climaxing that way. I require rather vigorous stimulation, and cannot get past being concerned for her comfort. Regardless, the feeling is incredible. We then  moved into a sixty-nine, and I worshipped her glorious pussy while she sucked my cock some more. My lady came on my face fairly quickly; an intense, pressure relieving orgasm driven by the long (for her) abstinence. She bid me to mount her, and as she lay on her back I did just that. I was quite ready, very hard and close to the edge. We kissed passionately while I thrusted and looked into her sexy, smoldering eyes. She held her legs open, and seeing that out of the corner of my eyes, I stiffened and came, copiously, intensely, and at length.  We kissed tenderly and giggled like teenagers at the quickness of our session.

On Saturday, I received a new cock cage in the mail, fairly early in the day. It's a 3D printed device from KINK3D, which I learned about after reading Denying Thumpers' Post. I was thus wearing it, in addition to the panties and chemise I had been instructed to have on when my lady arrived. We had some afternoon coffee in hand and proceeded to the bedroom. My lady had purchased for herself a sexy black piece of lingerie that covered her breasts, pussy and not much else, though there were a lot of straps crossing about here and there. Coupled with her silky, dark, unfurled mane, her beautiful, penetrating eyes and that delicious red lipstick, I proceeded to conduct an unplanned stress test on the cage. Fortunately, but inexplicably it did not burst into a thousand pieces. We kissed tenderly, and I caressed her body, kissing various exposed areas of her skin. Her scent drives me wild. Her hands traced lines across the cottony garment that enshrouded by torso, and then outlined the cage through my panties. She pulled them down and inspected, approvingly, this latest symbol of my devotion and dedication to her.

To be clear, I do not need a cage in order to be dedicated to her, any more than one needs a ring to ensure their commitment. The cages that I wear are indeed symbolic of my commitment to her. When we are together, we have fun with them, and I remove it at her pleasure. When I am alone it is comforting to know that I am still hers, always and forever. I have not found a practical way to remain caged 24/7, but I do wear one as often as I can. It helps me feel closer to her. It does also provide an obstacle to a casual self-caress turning into an uncontrolled masturbation session. Although a key is handy, the very act of interrupting the mood to fetch it and unlock is sufficient to break the chain of events.

My lady caressed and teased my pent-up cock. She kissed, sucked and licked my balls. She twirled her tongue around the cage, and even took it into her mouth. The sight of these actions, and the slight feeling that I was able to detect drove me wild with lust for her. She is such a sexy and creative lady, and I love how she is learning more and more about how I tick.  

Given that I was locked up, my lady decided to play with me in other ways. I had assured her that, having climaxed the day before, I was in no danger if I remained chaste this day. At this stage in our lifestyle, my lady consults me on these decisions. I welcome her questions and offer my honest feedback. I told her as much, and added that if and when she feels comfortable making the decision on her own whether to unlock me, I will obediently and happily comply with her decision. That goes for my orgasms. The very thought of giving up control of my orgasms is very erotic. It's a game, but not a game. It carries some amount of responsibility on her part, and I do not want to pressure her into bearing it. However, at her pace, and to the degree she finds it stimulating and rewarding, I am a willing participant. 

She retrieved a rather large butt plug, the very large black dildo, and the harness from my closet, along with a couple of other objects which will be revealed shortly. I inserted the dildo into the harness and then strapped it on to my body, the long ebony dong dangling dangerously above the black cage ensconcing my above average but relatively diminutive cock.  She then lubed my rear passage. It felt so nice to have her fingers encircling and probing back there. The plug went in with a bit of resistance; it had been a while since I'd had something in there, but once settled in it felt nice. 

So, to complete the picture, there I lay, in my chemise, plugged, caged, and with a large cock strapped to my groin, while my lady settled onto my face and I began to worship her delicious pussy. She was very engorged and wet; clear signs of how much she was enjoying our time. She sucked the black dildo while I ministered to her, and although I could not actually see her actions, in my mind's eye I could visualize every flick of her tongue, every movement of her lips around the head of that dark beast.

She decided that she wanted me to fuck her with it, and so after a long, but never long enough session of pussy worship, she lay upon her back. At her behest, I lubricated her back opening, probing with one and then two fingers. I pushed the pink dildo into her, and handed her the other realistic-looking cock that's closer in size to my own. I gently rubbed the black one against her opening, teasing her, and then pushed gently inside. In this position, I normally have more feedback, but the lack of sensation from the penetrating cock led me to proceed cautiously. I asked multiple times for direction on speed and depth, ensuring that all of this was pleasing to her. I got into a rhythm that worked for her, and she started sucking on the cock in her hand. 

I recently listened to a Shameless Sex Podcast that my lady found and shared with me. In it, they talked about how some men - submissive crossdressers in this specific instance - can be driven by lust to want to suck cock, even when in normal situations they are not tempted, and do not consider themselves gay or bisexual. I resonated with that observation, and while watching her suck, I had an overwhelming urge to join her. I asked if I could, and she said yes. She placed it at my lips and kissed it and sucked the head into my mouth, we went back and forth a few times.

The overarching emotion I felt was total love. I would do anything she asked me to, because I trust her and I love boundlessly. She allows, no embraces my own desires, and it elevates our pleasures mutually. I felt completely uninhibited by any of the so-called taboo practices that have filled me with shame and guilt over the years. So, here I was at this point. My own cock locked up tight, a plug in my ass, wearing a chemise, fucking her with a large black cock, and sucking cock with her. Wow.

She directed me shortly thereafter to her breasts, which I alternately suckled, while she worked a finger onto her clitoris, massaging that beautiful organ while being stimulated in all these other ways. Her orgasm was massive, so far as I could tell. I was elated that she had achieved such an intense climax, and honored to have been instrumental (pun semi-intended) in that event. We lay still for a bit, while her black friend remained inside her. Eventually, she had me pull out, and I kissed tenderly, repeating how much I love her.

We unstrapped and removed the various phallic accessories. I put them aside for later washing. I put my panties back on, along with a matching robe. I gave her a chemise and robe to wear, we relaxed with some wine, and then we had dinner like that.  Afterward, we watched a movie, snuggling and holding hands, feeling more deeply in love than ever.

All this, and we're only halfway through the Memorial Day weekend. 

Thanks for reading.

Jen




Friday, May 21, 2021

Yes, It's Definitely Working

I'm in a near constant state of arousal. It seems that my lady is learning to enjoy calling the shots on our sexual activities, and her acceptance of "all of me" has lifted an extraordinary burden from my mind. In addition, lately I've been in chastity almost constantly while awake, other than during shower time and after our little sessions each of the last two nights. I am still not able to sleep well while caged, at least not at this point, but it's ok.  I'm behaving myself.  "Hands off," she told me last night, when I departed her place. "Yes, ma'am," was my immediate reply. The feeling of being caged, knowing that she wears the keys on a chain around her neck, and knowing that I am abstaining as a sign of my devotion and love for her is a feeling that is difficult to describe; I'll use the word "sublime," I think for the first time in my life.  It seems to be a rather haughty word, but it fits.

On Wednesday, I spent the entire work day en femme.  I had recently purchased a pretty "Short Sleeve Floral Tiered Sheath Dress," black with purple flowers from JC Penney, and I was looking forward to wearing it.  I showered, shaved, put on my metal cage, and did my make-up. I'm not so great at make-up, but am getting better, and the process helps me transform into my feminine mindset. A bra, panties, my size C breast forms, platform heels, wig, jewelry and that dress completed the ritual. I guess I looked ok, but I felt really good.  Dressing that way helps alleviate a lot of the stress my job brings.

As the work day ended, I disrobed, removed my make-up, showered, and relocked myself, wearing male clothes, which is how my lady likes to see me.  I think it's too much for both of us at this stage for her to see me completely feminized. That day may come, but I'm happy to be for her what she wants me to be when we're together, and anyway I don't want to wear ladies clothes all the time. I truly like being able to switch between both modes.  It's sort of the best of both worlds.  Oh, and if the day does come for her to see me all decked out, it might be best if we started with me naked, and she helped me dress.  The process of helping, and the gradual transformation would likely be much easier on both of us.

After dinner at my place, she unveiled the purple lingerie she wore under her dress. We proceeded to enjoy a mid-week foray.  I stripped to just my panties and cage, knelt on the floor, and worshipped her body, focusing on her sumptuous lady parts as she sat comfortably on the sofa.  She was very wet and engorged. I was in heaven, and could have stayed there for hours, but she had other ideas. She bid me to fetch the largest dildo I have, a black cock that's probably nine or ten inches long and as thick as you'd expect such a creature to be. I did as directed, but also put on my own purple lingerie as a bonus. Returning to her beautifulness, I again knelt, and started rubbing the cock on her opening, which turned her on even more. I started to push it inside her, gently and slowly thrusting it deeper and deeper.  It needed a bit more wetness, so I licked the shaft as best I could, adding my saliva to her own moistness. I'll admit that it stoked my cuckold fantasies, watching that cock filling her, listening to her moans, facilitating the action with my own mouth. I sucked and licked her as best I could, occasionally adding more saliva to the dark beast that was ravishing her. My own cock, firmly ensconced in its metal cage, was straining for relief and attention, but we were focused on her. 

Being this aroused, I would have done anything that my lady wanted me to do. She decided that my real-life cock was what she wanted, so I uncaged and entered her. We continued in various arrangements. She eventually climaxed while using cock on her clitoris while I watched from below, almost in a trance, alternately looking into her beautiful, smoky eyes and watching her ministrations.  The memory of that scene will remain a long time, and it causes swelling inside my cage. We cuddled after, while my own cock returned to a flaccid state. No climax for me, not until she says it's time. She also told me, clearly, that she has no interest in actually having a third person participate in our love-making. I think that's the right call. We love each other so deeply, we have so much to explore together, and she is all I will ever need. I am hers, always and forever, and I have never been happier.

Thanks for reading.

Jen

Wednesday, May 19, 2021

It's Working

I underwent a hormone replacement procedure recently. The intent was to increase my energy level and also to sleep better during the night.  As we age, our hormone levels diminish, for the simple reason that there isn't an evolutionary benefit to people who are past their child rearing years to continue to have the urge to procreate. I suppose there is a benefit to the furtherance of our genetic material if the older folks would kindly step out of the way.  Well, I'm not ready to do that, fuck you very much. My lady isn't either, and it was on her advice that I went ahead and scheduled the procedure.  For the first week, I gained no benefit, but rather had some minor discomfort from the incision. For the next week, things were sort of neutral; I wasn't uncomfortable anymore, but also wasn't feeling any benefits.

I would say that things have changed now, and for the better. Last night, a Tuesday no less, we made out like teenagers on the sofa. It was erotic, suckling her breasts while they enveloped the two chastity keys that she keeps on her necklace, knowing one of them was for the device I was wearing. I have been alternating between my steel cage and my pink Holy Trainer, and this night it was HT's turn. We were both quite aroused, but stopped before going too far.  

My lady is still recovering from the weekend. We think she had at least five orgasms, two on Friday, two on Saturday, and one on Sunday. I never thought losing count of orgasms was a thing before. I abstained from climaxing until after her fifth one, but I was quite active with her. I pleased her orally and with penetration, repeatedly. Her climaxes are the highlights of our lovemaking, without question.  I definitely enjoy mine, and I know that she does. too. It's just that my climaxes are fleeting, lasting maybe ten seconds or so, while hers seem to go on for much longer. On the other hand, if I don't climax during our sessions, then I'm just that much more on edge, attentive to my love, and eager to please her the next time. In fact, I'm eager to please her in between, showing her in every way how much she means to me. That's not to say that my love for her is only driven by my sexual urges. No, no, it is far deeper than that. Spiritual, I might say if I believed in that sort of thing. I love her on every level. We are best friends, and we love being together and doing everything together. If we were not lovers (perish the thought!), she'd still be the best friend I've ever had.

The hormone replacement, for me at least, has not diminished my submissive or feminine feelings. If anything, they are amplified, along with my overall sex drive. I don't suppose I should have expected anything different, but I wasn't sure, and it was an interesting observation. I'm not a medical person, so my understanding of the whole hormonal balance thing is elementary. I do know that both men and women manufacture the "male" testosterone and the "female" estrogen, and that balance between them is important. I suppose I was curious to see if the therapy, which changed the balance, might change my desires proportionally. I'm here to claim a single data point in the experiment; the answer is a definite no. The rising tide has lifted all boats. Not only do I feel more sexually energetic as a whole, I also feel  stronger submissive and feminine desires in line with the overall increase in my libido.

My lady reassures me, repeatedly, that she loves all of me, and I believe her. I know it's true. Our recent times together have included my wearing a new animal print chemise with matching panties, and a cute little pajama set - tank top, shorts and a robe, both of which she commented on approvingly, and caressed softly.  After she did so, I pointed to the protrusion tenting my shorts and asked, "do these pajamas make my dick look big?"  She laughed and said, "no, your dick makes your dick look big."  :-)

We are both benefiting from the fortune that has befallen me in that regard. I didn't earn it, but am grateful for having been endowed with a larger than average cock. We fit together very nicely, and it feels so good to both of us when I'm inside her.  I can also last as long as she wants me to. In fact, my issues is generally whether I can climax at all, not whether I cannot hold out until she is satisfied.

That's another thing I've pondered. In most stories and blogs I read about submissives, crossdressers and sissies, they are undersized and subject to prematurely ejaculating. Thus, as the stereotype goes, they are humiliated and embarrassed by their lack of endowment and performance. The feelings wrap around upon themselves, and they get sexually charged by being subjugated by their ladies, to all sorts of predictable ends, including feminization, long-term chastity, servitude, pegging, public exposure, cuckolding, and "forced" bi-sexuality.  I don't read about men with larger cocks who can last for a long time having those feelings or finding their way down the path I just mapped out. It's not a surprise, really, but I do find myself at odds with at least part of that stereotype.

I am, to be sure, a submissive crossdresser. My lady and I have spoken at some length about some of the various aspects of a Domme/sub relationship that includes crossdressing. Neither of us finds embarrassment and humiliation to be appealing. We love, admire and respect each other on every level. Our sex life is an expression and extension of that. We verbalize and physically demonstrate our love while making love, and it is glorious. It happens that my sexuality is closely linked to femininity - worshipping her, submitting to her desires, putting her pleasure first, and feeding my own feminine urges - while at the same time using my masculine endowment to bring us both heightened pleasure.

I've pondered my own sexuality for decades, but have never had a partner who was so open-minded, adventurous, and loving before I met my lady, and thus have never acted other than in a solo fashion, with exaggerated fantasies as my stimulus. She is rather new to this whole aspect of sex as recreation and adventure. Her ex was not, shall be say, open-minded. We are exploring our new world, together. We are not in a rush. We communicate regularly about what works and what doesn't, at what pace we may proceed, and what routes we may explore. It's the journey that matters, not the destination. What is most important is that we are on this road together. Always and forever.

Thanks for reading.

Jen

Saturday, May 15, 2021

A Fantasy Weeknight

When he heard the garage door open, his heart skipped a beat, and his excitement grew. Even after all this time together, he still found that the highlight of his day was the moment she walked in the door, because he knew that for the rest of the evening, he would have her to himself and could tend to her every need, mind, body and soul. He loved her endlessly, and there was nothing better than being in her presence. She, likewise, loved him more every day, and grew to cherish their particular brand of marriage, though it had taken some time to see herself the way he did. He poured her a glass of her favorite red wine. Everything else was ready.

He had recently retired, but he was by no means idle. He filled his days with a variety of activities, some of which were for his own physical and mental well-being. He exercised, read books and played his guitar at scheduled times each day, finding that a rigorous schedule was still the most efficient method of accomplishing a lot, and he had a lot to do. He spent hours around the house, doing special projects, fixing things and such. He was not so good at regular cleaning, although he was learning how to be better at it and understood the standards that she required. She actually enjoyed cleaning, so it was not a task that she had transferred to him; at least not yet. However, he did most of the shopping, the laundry, and ironing, by now.

She continued to work, not because they needed the money, but because she loved what she did, and she was exceptionally good at it. She loved helping people feel better about themselves, and she loved the social aspect of her job.

Having loved him from the start, it had taken some time for her to adjust to his feminine side. She was not expecting that when they’d met, because he gave no outward indication at a casual glance. Once you see the signs though, it becomes more apparent. His legs and arms were clean-shaven. In fact, as she soon discovered, he was completely hairless below the eyebrows, and even those were trimmed short and somewhat shaped. He had not tried to hide his nature from her, and he unfurled his colorful flag just as fast as he reasonably could, striving to be honest and open while working to overcome his most dreadful fear of outright rejection and abject disdain. You do not begin a relationship by revealing your deepest secrets, that is simply weird.

Now, she knew of his penchant for dressing en femme, and encouraged it because she loved him, she knew that it made him happy, and she understood how the various threads of his psychological fabric were tightly interwoven. Surely, trying to extricate a single strand would jeopardize the entire tapestry.  No, she loved all of him, as he was. He sometimes would spend most of the day as his feminine alter ego if he had nowhere to be. Or if he did venture out, it might be in clothes that were from the ladies’ side of the store, but androgenous enough that no one seemed to notice. In the evenings, he would change his look, matching her preferences. She loved his masculine side, too, and he loved being what she needed him to be. He would wear something more feminine in the evening if she asked him to, which was a rare but not unheard-of occurrence.

He also wore a chastity device at nearly all times. It helped him avoid temptation, and its presence was a constant reminder of how he had surrendered himself to her, physically, emotionally, and sexually.  She now understood that limiting his orgasms led to feelings that he enjoyed immensely, a near constant state of simmering arousal, and deepened submissiveness.  She saw that he was even more eager and creative in finding ways to please her and make her life easier and recognized the mutual benefit of his servitude.

This day, for no particular reason other than to express his love, he set out to make a special evening for her. Pleasant surprises are an important part of a relationship. He did the meal planning and prepared a list of ingredients he required. Having worked as her assistant in the kitchen, he’d watched and learned. To be sure, his skills, knowledge and creativity were the second best in their household, but he was a far better chef than any other non-professional that he knew.

She had been vegan for years before they met, and while he had not been, he did eat a healthy diet, and so it was easy for him to immediately switch. Her amazing culinary skills quickly made him forget what eating used to be like. His realization of the cruelty surrounding animal-based products cemented his commitment to this new dietary routine. He was now vegan. He’d be anything she wanted him to be. Not only because he loved her, but because he trusted her, and he respected her brilliant mind and empathetic heart.

She walked in the door, and he greeted her with a smile, a long and enveloping hug, and a soulful kiss. He took her coat and bag from her and placed them where they belonged. He followed her into the kitchen, where her glass of wine awaited, shadowed by a fresh bouquet of flowers. She smiled and thanked him. Dinner was simmering, the table was set, the animals were fed, and music was playing in the background; there was nothing to do but be with her while she relaxed and unwound from her day.

She sat comfortably on the sofa, and he knelt before her. He positioned a foot basin, filled with warm, scented water just a few minutes prior, slipped off her shoes, and she placed them in the water. He loved her beautiful, sexy feet, as he did the rest of her, and knew that after standing for most of the day that they would be aching. She feared the aroma from a long day on them would be off-putting. He allayed her concerns with this routine of bathing them. While she soaked, he joined her on the sofa. She needed some time to catch her breath after a busy day, and so he just sat next to her, gently holding her hand. He could almost feel the tension of the day leaving her body.

After a few more minutes, he knelt again, taking one foot onto the towel draped across his lap. He dabbed at it until it was sufficiently dry and repeated the process with the other foot. Moving the basin out of the way, he brought out some lotion, and massaged it into her skin, further softening them and chasing away the tension that remained. They made eye contact, and she smiled. She could not tell who was enjoying this ritual more. When he finished, he reverently kissed the top of each foot and replaced her slippers.

They sat together for a while longer, and then she decided it was time to eat. She sat at the head of the dining room table, and he prepared and served their plates, then sat at the side of the table. As they ate, she related the stories of her day. He listened closely, asking questions, filling in the picture in is mind. She commented on the delightful meal that he’d prepared, and he was pleased that she found it delicious. She asked about his day, and he related the various events. She listened closely and wanted more details because she loved him.

Afterward, he cleared the table and set about to clean the kitchen, which did not take long, as he always cleaned as he went while cooking. “I’d like a bath,” she said to him, “tell me when it’s ready.” She went into her home office to tend to some post-hours business. He quickly finished his kitchen task and proceeded to draw the bath. It was a beautiful large free-standing soaking tub that they had installed in their recently remodeled Mistress Bathroom (Master Bathroom was just the wrong term). It could be accessed from all sides, which was perfect for their arrangement. Setting the water to the correct temperature, he added her favorite bath gel. He ensured the rest of the bathroom was neat and tidy. He set the lighting, lit some scented candles, and changed the music to one of her favorite playlists. He put some towels on the warming rack and ensured that her robe was within reach.

He heard her on the phone with a client as he approached her office, and he waited patiently until she finished. “My love,” he called to her quietly from the doorway, “your bath is ready for you.” She looked at him and smiled. She was getting used to his services and starting to accept the fact that she was deserving, but still she by no means took him for granted. “Thank you, sweetie, I’ll be there in a moment.  Why don’t you put on something sexy, and then you can tend to me in the bath?” It was not a question, it was a gift.

He took leave of her to do as she commanded.  He stripped and went to his special closet, choosing a new pink chemise with matching panties that she had not seen before.  As the garment covered his body, he slipped into a deeper state of submission. He padded into her bathroom, and she caressed his silky fabric approvingly. He slowly undressed her, removing her work attire, and then her undergarments. She stood there wearing only a smile, took his hand and allowed him to guide her into the perfectly conditioned water. At her behest, he fetched another glass of wine, and knelt at the side of the tub while she closed her eyes, sipped and relaxed. She had never been more beautiful as he watched her body soak in the warm bath.

“Wash me, now,” she instructed. She tilted her head back slightly as positioned himself at the head of the tub. He used a cup to pour water repeated onto her hair, careful to avoid it running onto her face. Sufficiently wetted, he gathered a dollop of her shampoo and began to massage her scalp and follicles, tending to her with reverence and appreciation for this high honor. Rinsing her, he repeated the actions with her conditioner. Moving to the side now, he took her each arm in turn and gently washed and rinsed them. She laid her head back, with her eyes closed, reveling in his ministrations. He washed her chest, spending more time than necessary ensuring her breasts were clean. They smiled at each other. The stimulation of her nipples always led to her arousal, and this time was no different. She brought his head forward, he suckled her breasts, and she cooed.

She leaned forward and he scrubbed her back. Then he proceeded to bathing her gorgeous legs and feet.  Oh, how he loved to tend to her body. He could not contain himself, and as he rinsed her feet, he gently took each toe in his mouth and sucked them. She watched him, amused, enthralled and inspired. He was performing over and above his expected duties. It was clear that the more she took charge, the more she required of him, the deeper his submission and devotion grew, and the happier they both were.

She reserved the cleaning of her womanly parts to her own hands, in part for hygienic reasons, but also to tease him further.  He watched her ministrations, reflexively licking his lips. She turned over to her knees and had him attend to one final region. He washed cheeks of her sexy backside, and then worked his hands up and down her intergluteal cleft, focusing repeatedly on her opening.  He circled it with his finger and probed inside it. He pushed inside with one soapy finger, and then a second.  He repeated, while listening to her moans of satisfaction.  “Make sure you get me nice and clean there,” she commanded, “clean enough to eat.” He grew firmer in his cage. He had confessed to her is desire to worship her ass with his lips and tongue, and she had thus far declined. It seemed that this night she would grant him the honor. Another step on their journey. He shook with anticipation as she emerged from the bath and he applied the towel to her fabulous female frame. “Go and turn down the bed, place some pillows in the center. Brush your teeth, and wait for me,” she instructed.

He did as he was told, and she came into the bedroom, naked and beautiful. She kissed him and grasped his caged cock and swollen balls.  “If you do a good job worshipping my ass tonight, I might let you out.” He had not needed the extra motivation. This was yet another fantasy, coming true. She laid on the bed, her gorgeous glutes prominently displayed. He knelt behind her, and softly kissed her cheeks, then more passionately. He licked her cleft, repeatedly, long slow flat-tongued movements that heightened their arousal. He parted her cheeks just a bit more and looked at her opening. He knew the term ass-kisser was derogatory. He was now an ass-worshipper. But it was not an act of humiliation or punishment. It was an act of love, on both their parts. A new way for him to demonstrate his limitless love for her, and a new way for her to accept it.

He kissed her opening, gently and repeatedly, with closed lips, both of them getting used to the feeling. Then, without thought, he opened his mouth and kissed her more passionately. She let out a grateful moan, and it inspired him. He kissed her more deeply, more urgently. His tongue flickered out across her flesh. It circled and darted, checking her comfort level. She shifted, raising her ass a bit higher. He pressed further against her opening with his lips.  He stiffened his tongue and probed, pushing past the opening to the vestibule of her most private region. He wiggled it around and she spoke, “oh, that feels soooo nice.” He pushed further and further, until his tongue was as far into her as it could go. He plunged and swirled, kissed and licked, bathed and caressed her opening. She reached one hand under and began to stimulate herself.  He continued his oral homage as she masturbated. He inserted one, then a second finger into her very wet pussy, sawing in and out at a tempo that varied from that of his tongue. She voiced greater and greater sounds of pleasure as her approaching orgasm gathered strength. Then, like a Tsunami, it crashed upon her. He could feel her convulsions on his tongue and his fingers as her muscles squeezed and relaxed in great spasms of ecstasy.

He continued ministering to her, feeding her pleasure, mindful of her own actions. When her orgasm subsided, and he sensed her hand moving away, he withdrew his fingers and his tongue. She lay in post-orgasmic bliss. He hurriedly went to rinse his mouth and brush his teeth, and upon returning, lay next to her, kissing her face, caressing her body, and sharing the joy that she felt. They moved the pillows, allowing her to lay flat and comfortably. He continued his soft caresses, and gentle kisses. He expressed how much he loved her and thanked her for allowing him to worship her in that way. “It won’t be the last time,” she replied. They lay quietly together for a time, and he realized that she’d fallen asleep. He arranged the covers over her body, removed his lingerie, and lay next to her, watching in awe this most beautiful and wonderful lady with whom he had so totally fallen in love. There would be no release for him this night. Still, he had never been happier than at that moment.

Monday, April 26, 2021

Jennifer Sort of Makes an Appearance

I slept at my lady's house over the weekend. It was after our little adventure that I described in my last post.  After she left to tend to things at her house, I started taking care of my tasks at my own place before heading over. As I prepared to go, I decided to wear only ladies' clothing.  Ladies' collared shirt (buttons on the other side), panties (all I wear, anyway), jeans, socks and sneakers.  All the externals would pass without a second glance in public 99% of the time. I know, because I frequently dress that way when I go out to run errands.  I don't look feminine, mind you.  No make-up, wig, or jewelry, just a guy proving that hardly anyone looks closely at you anymore. They're all pre-occupied with their phones.  

Anyway, I decided to be bold, and brought only a chemise, panties and a ladies short grey robe for the morning.  The chemise is my nicest one, and my lady has seen it before,  It's from Macy's, the Jenni brand. I don't think they sell that particular style anymore, but I found this image of it.

I didn't sleep well, so I went to her guest bedroom to finish out the night. I awoke later than her, and boldly donned the chemise, panties and robe, and padded into the kitchen to kiss her good morning and have coffee.  

Let me just say, she's amazing. We hugged and kissed, and sat down to enjoy our coffee.  I looked at her, bared my shoulder to show the strap and said something like, 

I thought I'd wear this, is that ok?

I noticed it when you first came down. Yes, it's ok.  Does it make you feel good?

Yes, it does. 

My eyes welled up.  She saw that, stood, came over and hugged me. She said,

I love all of  you.  I want you to be happy.

I kissed her, and I cried.  For years, I've been guilt-ridden by my longing for woman's clothes, and femininity in general. I've lost so much - a marriage, friends, family.  And here is this woman.  This amazing, beautiful, intelligent, strong, caring, loving woman who loves all of me.

I cannot yet fathom the fortune that has come to me. It's difficult to even write about it without welling up.

Thanks for reading.

Jen

P.S. I just realized that the name my favorite outfit by Jenni is so similar to my nom de plume.  It's either coincidence or some deeper connection that I'd not noticed before.  It can also be seen in my icon.