Lisa and Jack: Crossdress Fun

Story Info
Lisa explores a new fetish to liven up their sex life.
3.9k words
4.62
60.1k
77
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here
CDWife
CDWife
38 Followers

First of all, if you are looking for some story about a guy who turns into a cockslut - this isn't for you. Our main character doesn't dress up for the first time and realise that he is really a girl either. And just to make sure, the wife is not sleeping around or trying to magically turn him into a girl either.

This is a story about a couple looking to explore each other.

Good. So let's begin.

*****

My wife Lisa and I had been married for 2 years when things started to dry up in the bedroom. Each time we had sex it felt like more of an obligation than something that we actually wanted to do. This was very disappointing for me as when we were first together the sex had been amazing; spontaneous sessions and even Al fresco romps had been the norm. I guess that old cliché about marriage is true after all.

I decided to mix things up a little one day by buying a small blue butt plug from an adult store near my work. The sort of dark and secluded place where you wouldn't find the sort of people I usually socialise with. My wife and I are both professionals in the city and seem to keep a very uptight and conservative group of friends. To put it simply - I could not be seen here. I pulled the collar of my jacket up and wore a flat cap as I entered the shop. Now I looked more like I should be in that kind of place.

When I surprised Lisa with it later that night she was a little cautious at first. She had never tried anal before and she had heard that it really hurt. I told her that it was only a small plug and that I would take it slow with her.

After a while she was more open to the idea and agreed to try it as long as I would try it too. Not thinking that she was serious, I accepted this and started caressing her body with my hands. I was very excited by this new taboo and I could feel my hard-on pressing against my jeans as I started to pull off her work clothes. I soon had her stripped down to her underwear and lying on our bed. I pushed my way between her legs started ravaging her with kisses and licking my way down to her panties.

They were a glacial blue silk with a white lace trim around the edges, the matching bra now discarded on the floor. I could tell that she was also excited by the new power in our love-making and I decided to tease her by slowly lowering the panties inch by inch, each with a kiss or a lick. I finally removed the panties completely and started licking long tongue strokes from her hole to her clit.

After a little while I moved further and further back. I then slowly pushed her knees back into he chest, exposing her puckered asshole. She tensed, but I held her hand to assure her that everything was okay. I then moved in and lightly kissed the top of the ring. She shivered and I started to lick around it in slow circles, licking slightly harder each time to ease open her tight ass.

By the time i reached for the toys she was quite relaxed. I lubed up the plug and ran it around the outside of her hole before placing it in the middle of the slight opening. I pushed it slowly in. Each movement was met by a moan and a whisper of "more" or "slower". When the whole toy was inside she pulled me up to kiss her and we lay like that or a while.

I then returned to between her thighs and started to luck at her clit. With a little tapping on the plug I soon had her cumming heavily, dripping down to her still plugged hole. Lapping this sweet juice from her pussy, I slowly pulled out the toy ad she yelped in joy as the last bit slipped out.

"That was amazing," she said, "the best cum I have had in a long time!"

"I thought you might enjoy it," I smiled.

We cuddled for a while and went to sleep, obviously worn out by all the excitement.

We expanded our anal play and soon I had convinced her to take my cock. Although bigger than any of our toys, I'm around 6", she took it well and enjoyed the fullness of my dick deep in her ass. She never really asked to do it however, and always preferred to take it in the pussy than the ass, so I stopped asking too.

Soon it was limited to once every two months and our sex life flatlined again.

One night Lisa was restless as we followed our usual routine of eating our diner whilst watching the TV in our living room. She ate very quickly and waited impatiently for me to finish my food.

"Jack, I have a bone to pick with you," she stated.

"Yes?" I replied wearily, wondering what I had down now - the toilet seat must be up again.

"Well, when we first played with my ass, you said that you would try it too. And yet, you never have,"

"I thought that you were joking because you were worried about trying it. And in any case you haven't exactly been begging to do it!"

Lisa moved in close to my face and grabbed my dick through my trousers.

"Well I want to do it now. You said you would."

Dragging me from the couch she led me to the bedroom and hurriedly undressed me. I stood there butt naked and a little shocked by what was going on. She pushed me back onto the bed and started to suck on my cock and lick around my balls. It was hard in no time and I was getting close when she suddenly stopped.

"What's wrong?" I asked. "Please don't stop! I'm so close!"

She reached into the bedside table and retrieved a tube of lube and a small blue butt plug. I had forgotten that this was why we had come here.

"Remember this guy?" She asked with a wide grin on her face.

"Yes I think so, " I replied. "But you aren't seriously going to use it on me are you?"

In response she pushed my legs back onto my chest and I could feel myself become very exposed and vulnerable. She applied some lube to her finger an slowly rubbed around my tight asshole. The sensation was unlike anything I had felt before and it tingled through my whole body. She smiled as she watched my reaction. She lubed the plug and guided it slowly inside me. It felt big, though no more than thumb width, it filled me. When I felt the base touch the outside of my ass I knew I had take it all and was very happy with myself.

Lisa crawled up beside my and kissed my passionately. It was the most intense kiss in my life and I felt an emotional connection that I had never felt before. As we kissed she started to pull the plug in and out of my ass and she moved my hand to my cock. I exploded all over myself and even on the side of her face as we kissed. The sensation seem to last long that usual and felt deeper within me.

I passed out in ecstasy and woke up with my head on Lisa's chest and my leg over hers. She was stroking my hair and in that moment I felt closer to her than I had in a long time.

After this experience Lisa was more and more into playing with my ass. In fact, our sex life in general was amazing. She started to use the other toys that we had used on her ass and even some of the rabbits that she fucked herself with whenever I was away on business.

However, even though she would always be close to me when she was stretching my hole, she would often complain about how she felt disconnected from the toy and me.

After a longer business trip of mine, I came home to a very excited Lisa.

"I know how to be closer to you now," she beamed.

"Yes?", I said leaning in for a kiss.

"I will actually fuck you."

"Don't you already do that?"

"No I just play with a toy in your ass. I want to be part of it. I want to feel like I'm in you!"

"We already tried the fingers..."

Fingers are fine when clipped and slender. Ladies fingers often have very long nails though, and these do not go well with my ass. Lisa has long nails. Latex gloves and cotton balls do help however.

"I know! But this is better, look!"

She stepped out from behind the kitchen counter and there at the meeting of her two long, slim legs was a pink dildo strapped around her waist.

"You bought a strapon?" I asked, amazed but very turned on by the sight of it dangling there. I had wanted to try I before but was always too scared to ask. I thought that she might see it as too far.

"Yes. Want to come and try it out?"

I crossed the kitchen and stroked the shafted lightly. It was a soft touch rubber and was shaped in a stiff upwards curve.

"It is meant for beginners," she said, pulling me close so that I could feel the hard dildo press against my cock. I knew that she could feel it caressing her clit with every movement. I loved the sensation of the slightly bendy toy being thrust against me.

She led me to the bedroom where we lay on the bed kissing and undressing each other. Finally she told me to take off my briefs and lie on my back. I did so slowly. For some reason, though she had penetrated me countless times,this felt different.

She kissed down my body and licked my cock and balls. She then moved right down to my ass. She had never done this before as she always said that she was worried about there still being shit there. The skin between my ass and balls is very sensitive so I never had any complaints. Today she was licking it straight on and was pushing her tongue hard onto the tight hole.

"It actually tastes quite good," she said, lifting her head for air, her ass propped up above her. "It's salty like your balls"

After using a medium sized plug to open me up a little she began to lube the strapon. She moved in close to me and kissed me tenderly.

"Don't worry, baby, I'll go slow. Nice and easy, just say if it is uncomfortable for you"

"Just be gentle," I say.

It feels like the first time. Like I am a virgin girl about to have my cherry popped. My heart is racing as she raises my legs slightly so that she has a better angle.

She pushes the head of the dildo against my slightly open ass and slowly moves in. My hole widens to accommodate her bulbous head and closes around the shaft as she begins do move in and out in small movements. As she keeps pushing the cock deeper into me I feel her shift and I open my eyes to see her above me, perk boobs swaying slowly as she moves in and out.

She leans down and kisses me and at the same time pushes the whole length of the dildo into me. I cry out in a mix out pain and pleasure, muffled by her mouth.

"Is that okay, baby?" She whispers in my ear. "Do you like my cock inside you?"

"Yes" I whimper, "I love it, I feel so close to you."

"I know, it's because I am inside you. I feel like I have so much control!"

"I feel vulnerable, but I like that feeling when its you who is in control"

"That's how it feels when you are inside me, it really is a role reversal"

She fucked me on my back for a while, fucking hard and fast mixed with long deep thrusts, before flipping me onto my knees. This felt amazing and she could fuck me really hard. I am not sure if it is the angle but it was such an intense feeling as Ah pounded me. I was so close to coming that I had to tell her to stop before I covered the sheets in my come.

She pulled out and lay on her back, stroking her lubed cock.

"Now let's see you do some work. Sit on my cock and ride it up and down."

I obliged and knelt above her, fumbling with the the dildo to find my still wide hole. I slid down the shaft and started to bounce on the springs in the bed. Soon Lisa started to thrust up into me and it was not long before I came all over her boobs and I even got some in her mouth as she stared open mouthed at my huge climax.

I collapsed onto her and woke in the sane position with her stroking my hair. I kissed her deeply and she started to fuck me again. Not able to take any more I rolled off of her onto the bed. She started to trace her finger across my stomach and I soon realised that it was covered in the cum that had been on her body.

She leaned right over and licked a long strip of it from around my belly button. She then came up to my face and kissed my passionately, forcing the cum into my mouth. The taste was very sharp and unpleasant. No at all what you think a sugary liquid should taste like. I pushed her away, asking my she would do something like that.

"Well if you get to be fucked then you need to be willing to take the cum too. You are in the female position after all"

"I don't remember that being part of the bargain. If it was your cum I wouldn't mind, but I don't fancy eating my own thank you!"

"Suit yourself," she said playing with the still wet strapon. "I would clean up if I was you, a lot of lube went up and it must come down."

I cleaned up in the en suite and climbed back into bed, a little lube still dribbling from my ass. She drew me in to her chest and she stoked my hair as I fell asleep.

We started fucking with the strapon almost as much as we were having regular sex. One day Lisa decided to make it a little more exciting as we were getting ready for another play. She was strip teasing for me as she slowly pulled down her panties to her ankles, her legs still straight. She then paused before picking them up and throwing them at me.

"Put these on baby, they will just about fit you and you will look so good in them with your tight round ass"

I wasn't sure about this. It felt a little gay to be honest. But then again, I also wanted to be fucked. I stepped into the panties and slowly pulled them up my legs. They were a pinkish lace with a flower design. They felt amazing. Why don't men's underwear feel like this? Why are they so boring when we could have all the choice that women have? I looked at myself in the mirror, admiring my ass in those snug panties, my hard dick peeking over the top.

"I knew you would look great in those," she whispered from just begin me. She put her arms round me and started to caress me. "Maybe you would look good in some of my other stuff"

With that she opened the wardrobe in the corner and started pulling out skirts and summer dresses. Holding them up to me one by one she finally picked a bright yellow summer dress with a frilly edge.

"Here, put this one on," she said passing it to me. It felt soft and light to the touch.

"I don't know," I said nervous about what this was leading to. "I mean, I'm not a girl. Would you not prefer me in more manly things?"

"Don't worry, it's not like I'm a lesbian or something." She reassured me. "I'm not trying to make you into a woman. It's just... Well when you you see me in tight or sexy clothes, it turns you on, right?"

I nodded in assent, still holding the dress in my arms, the frills tickling my legs.

"Well when we are doing this role reversal thing... Shouldn't I get to see you in those sexy clothes? And more importantly, shouldn't you get to feel sexy? More in the role of a lady being seduced and treated gentle before we fuck."

I thought about this for a while, it was an interesting idea. I had spent my whole life chasing girls and not really being seduced myself. It was very inviting, and the panties were very comfy and sexy looking. What hurt could a dress do? It would only be the two of us that knew, and she wouldn't tell tell anyone...

"Okay," I said. "I'll wear it if you want me to. But you can't ever tell anyone about this, not even if we end up in a messy divorce."

"Of course not!" She laughed. "How do you think I would con out in all of this?"

I went to pull the dress over my head but she stopped me just as I had it around my neck.

"You need to step into this dress," she said. "Plus, you can't put I on without this"

She was waving the matching pink lace bra in her hand. I hesitated. Had I made the right choice? But she was already handing me the bra. I struggled with it behind my back. I had taken many of these off in my time, but never put one on!

"Here." She said clipping the bra for me and kissing my lightly on the lips. "Now let's see you in that dress"

I stepped into it this time and pulled it up so that I could put my arms through it. My wife I shorter than I am but is still quite tall for a woman. This meant that we have the same shoe size and not as it turns out, the same waist. We are a little different in height though, so the dress only made it part way down my thighs.

She helped with the zipper and then stood back to admire her work. She smiled.

"A little make up, deal with your legs, maybe your hair... And you're the perfect little lady, I'd certainly fuck you."

I go red from this, not caring what she meant about the legs or hair. I was gonna be fucked good tonight.

She laid me down on the bed and climbed on top of me, kissing me deeply. She groped at my chest through the bra. It felt more sensitive, even though I now had two layers on. I let out a moan.

"Do you like that, baby?"

"Yes!"

She lay down next to me on the bed and began to run her hand up my leg, under the skirt of my (her) dress. He started to rub my cock through my lace panties. It felt amazing as she ran her hands up an down it, cupping my balls. She then flipped me on top and began to caress my ass and play with her fingers along the edge of my panty line.

I could tell she was getting very horny to fuck me. I loved this! She left me on the bed and went into the bedside cabinet for her strapon. After making sure it was all secure she gently pulled my panties down and threw them away. She pushed her head under my skirt and, instead of sucking me off, focussed only on my balls and ass. This was very teasing and resulted in a huge hard on, begging to be sucked. But she didn't suck it.

She lubed up my ass an her cock and smoothly pressed into my ass. My dress spread around me as she came deeper inside me. I reached for my cock, ready to explode already but she grabbed my hand.

"Not yet, not yet," she said, a sly smile on her face. "And girlies don't have dicks to play with, not yet anyway!"

She leant forward and kissed me as she picked up her speed, fucking me faster and faster. She moved my legs from round her to on her shoulders, to both over one shoulder, to spread straight and wide. It felt amazing and the tight bra and frilly dress adding to the tingling sensations running through my body.

She flipped me onto my knees and had me bounce on top her, kneeling behind me. She undid the zipper and pulled the shoulders of the dress down my arms. She then groped and pulled my chest back into her. I could feel her perk tits pushing into my back, the pointed nipples rubbing up and down.

As she squeezed my nipples under the bra I reached back and grabbed her ass, pushing her cock deeper inside me. In response she rolled me forward and fucked me doggy style. She scooped the yellow fabric of the dress into the middle of my back and began to spank me and hold my hips.

Finally she told me I could touch my cock. I started to play and I was on the edge when she whispered that she wanted me to catch the cum in my hand.

I came in a huge gush of cum that covered my hand and a large part of the bed. I was shaking from the orgasm, her cock still inside me, rocking back and forth. She pulled out and took my hand. She licked the cum from it (still enough to fill her mouth!). She rolled me over in my dazed state and kissed me deeply, forcing my cum into my mouth. It still taste sharp, but not as bad as before.

"Remember that this is the only man cum you can eat!" Lisa said, aware that I wasn't reacting as badly as last time. "Only your cum and mine can pass those lips"

"You don't have to tell me that!" I say sleepily.

"Good. We'll be a good girl and take off that dress and bra, clean up and come back to bed"

I did as she said and clambered into bed beside her. She pulled me in close an kissed me again. I could still taste the cum but I didn't know if it was me or her. I found this very amusing and went to bed with a huge smile on my face. What a night.

*****

Thanks for reading! I hope that you enjoyed the story and would like some constructive feedback. And yes, this is written by a woman based on real life fun with my husband. Plenty more stories to share if you like it!

CDWife
CDWife
38 Followers
Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
21 Comments
AnonymousAnonymousabout 2 years ago

Wish that was me

AnonymousAnonymousalmost 3 years ago

STILL wishing you'd write something else!

Or have you been using a different "pen name"?

AnonymousAnonymousover 4 years ago
Excellent

Loved your story. No public humiliation, no whips, no savagery, no mention of the dreaded "S" word. Just some loving fun and enjoyable for both. Great stuff, thank you.

AnonymousAnonymousover 7 years ago
just like me and my wife

I too have had similar experiences with my wife. I secretly always wanted to cross-dress but I never told her. When she actually suggested that I put on her panties and bra it was like heaven to me. Now we regularly have role-reversal sex -- she's the man and I'm the woman. I dress in sexy lingerie, she in men's underwear, and she then feeds me her big strap-on dildo to suck and then she fucks me deep and hard with it.

Please tell more stories. This one was great.

AnonymousAnonymousalmost 8 years ago
I like all men's cum

I love it when my wife snowballs me with my own cum. However, she enjoys it even more when she watches me suck another man's big cock and swallow his cum. I'm a sissy slut husband CD who loves sucking cock and getting fucked, especially in front of my wife. Please tell more stories.

Show More
Share this Story

Similar Stories

Her Presents She had a number of surprises for him.in Fetish
Dressed To Please Kate Husband and wife both enjoy the femme side.in Transgender & Crossdressers
Wife's Idea Wife teaches Hubby new tricks.in Group Sex
Busted Wearing Panties Ch. 01 He's caught by his stepdaughter wearing her panties.in Transgender & Crossdressers
Shemale Surprise A married man is seduced and taken by a friend of his wife's.in Transgender & Crossdressers
More Stories