My wife and I have really grown apart, especially in the bedroom. We’re both equally at fault but we may have taken a turn for the better.
About a year ago I was home alone for a few days while the wife and kids were away for a funeral and I began digging into my past days as a straight man who likes to dress in women’s clothing and occasionally shove a vibrator up his ass. That lead me to digging into my wife’s dresser drawer and putting on some of her clothes and pleasuring myself. Fast forward a year and I’ve grown my hair long, lost about 30 pounds, acquired an impressive wardrobe for in and out of the bedroom, and I have a very manly boyfriend named Dave whom I have completely fallen in love with. It’s amazing how quickly things can go from innocently putting on your wife’s underwear to becoming an absolute whore for some man you met while putting up a TV wall mount.
The wife and I still have sex about once a month but it hasn’t been anything to write about. Bland and boring and neither of us is really all that into it. More like going through the motions. Well, things may have taken an interesting turn.
The kids were away for the night, staying at their grandparents while my wife and I went out to a comedy show and dinner. When we got home we were buzzed but not drunk and we just sat on the couch and enjoyed the silence for a moment before we started kissing. After a few minutes of making out we stopped to catch our breath and my wife made a joking comment about my long hair and weight loss.
“You’ll probably fit into my clothes better than I do.” She said sarcastically
“Probably? I know I do!” I answered boldly
We had a few more drinks and kisses, even a little groping and then out of nowhere she stands up and grabs my hand.
“Come with me!” She said yanking on my arm and leading me upstairs.
She started digging through her drawers and threw a pair of her jeans at me.
“Try these on.” She said as she reached for a shirt as well.
I was a bit taken back as I began to wonder if she knew my secret or was this merely a coincidence? When we were dating 20 years ago, we had an extremely different sex life. She was aware that I sometimes enjoyed dressing up in women’s clothes. It was just something I had brought up during the early stages where we were getting to know each other. When we started getting serious I had all but forgotten about it because I was getting laid so much, wearing women’s clothes and that bisexual side of me got pushed way down and almost died.
“I can’t wear your clothes without underwear.” I said jokingly
“Right, of course. What was I thinking?” She said laying on the sarcasm as thick as she could
Ironically she pulled out the same bra and panties that I wore a year earlier when all this started. She threw those at me as well and told me to put them on.
By this point both of us were now drunk and she certainly didn’t seem to know what can of worms she was opening, and I had no clue where this was headed but I just went with it.
“I’ll be right back.” I said collecting the clothes and heading towards the bathroom
“You can’t get naked in front of me anymore?” She asked
I answered with some comment about being a lady not a whore which is definitely not true, but really I just needed a minute to collect myself.
I went into the bathroom and just stared at myself in the mirror while trying to slow my breathing and heartbeat. I felt like I had just ran a marathon I was so nervous and scared. I finally began taking off my clothes and putting hers on. I started with the bra and panties, ran my fingers through my hair once as I gazed at myself in the mirror once more. That sight calmed me down quite a bit as I still get incredibly excited seeing myself in women’s clothing. I finished by putting on the shirt and pulling up the jeans. I was right, they fit me better than her.
“Told you so.” I said laughing as I exited the bathroom
“Jesus Christ, they do fit you better!” She said amazed “…oh we gotta complete the look.” She said dragging me back into the bathroom.
She got out a bunch of her makeup and started putting it on me without even asking if I was okay with it. I obviously was 100% ok with it but I didn’t give it away. My man Dave once took me to get my hair and makeup done for a date we went on but otherwise I had been doing my own makeup for the past year and doing a pretty subpar job of it, so the thought of having a woman who really knows what she’s doing excited me.
Once she finished with the makeup she started doing my hair. And again I was excited! When she was done she just stood there staring at me. Baffled, amazed, amused, all of which she admitted to.
“How the fuck do you look this good?!” She asked
Over the course of the next few weeks we had sex 10+ times. I know this because we went through an entire box of condoms. We hadn’t had sex 10 times in any calendar year since getting married so this was bizarre to say the least. During those few weeks we would talk after sex and she regularly brought up the night she dressed me up.
“You’ve brought that up a few times now. What’s up with that?” I asked
“I don’t know.. it was kind of sexy.” She answered nervously “…I remember you telling me a long time ago that you would sometimes wear women’s clothes. Does that still do anything for you?” She asked
“Honestly, yeah. It was kind of hot.” I answered playing it down a bit.
“Is it something you want to explore in some way?” She continued with her questioning
“I’ve always liked doing it honestly but how are we going to do that? You want me to dress up as a woman and pretend we’re lesbians?” I asked with a bit of a laugh
“I’ve always wondered what it was like to be a man. I don’t know how we go about all this. I’m just thinking out loud I guess. I suppose it all depends on what each of us is thinking and willing to try.” She rambled on
“You’ve know me for over 20 years. Even though our sex life has become a bit.. slow, or unimaginative at times, you know I’m up for anything. Especially if you’re enjoying it.” I explained “…I’ll do literally anything you want. Just name it.” I continued
I had come home from work a few nights later and I was excited because I was going to go over to Dave’s house and have him fuck me all night. With all this talk around the house with my wife, I had become so horny and hot for Dave’s dick that I couldn’t take it any longer.
As soon as I opened the door I felt my phone buzzing. When I checked the message, it was from my wife.
“I have a few errands to run after work, can you please feed the kids?” It said
After agreeing to do as she asked, I had to call Dave and give him the disappointment that I wouldn’t be able to come over tonight. He wasn’t nearly as upset as I was.
I got the kids some dinner, started them on their homework and went downstairs to my little man cave. My wife finally got home around 9pm which was way later than she had told me. I heard her come in the front door and head upstairs to see the kids before they went to bed. Shortly after she came downstairs to see me. I was stunned! She had cut her hair! It was almost down to her waist this morning but now was a short little pixie cut!
“Wow! You’re missing a ton of hair!” I yelped
“You like it?” She asked
“Yeah, you look cute. And younger.” I answered
“C’mon upstairs with me.” She said with a devilish grin
When I got into the bedroom, there were a few bags sitting on the bed. I couldn’t tell where they were from.
“You remember when you said you’d try anything?” She asked nervously
“Of course… what are you up to?” I responded
She grabbed me and once again pulled me into the bathroom where she did my hair and makeup. This was unbelievably unexpected but began to evoke some conflicting emotions in me. One, it started to quell the anger of not getting to go see my man. However, as she went on and started looking more and more glamorous, I was getting unbelievably turned on and missing Dave. I wanted to look like this for him!
My wife quickly exited the bathroom and returned in seconds, gone just long enough for me to adjust my increasingly erecting penis in my pants, and admire how hot I looked.
“You’re super serious about doing anything?” She said
“Yes! You should know me better than this.” I answered annoyed but laughing
“Put this stuff on and come join me when you’re ready.” She said handing me a bag and leaving the room
I opened the bag and pulled out the contents. The first thing I grabbed was a pair of fishnet stockings. The next was a black lace thong, that I chuckled when I saw because I have this exact pair at Dave’s house. Lastly, there was a black silk and lace teddy that was super soft and super sexy. I removed all my clothes and started putting the women’s clothes on. When I was done I looked in the mirror and couldn’t believe how hot I looked. I tried so hard to keep my dick between my legs so it wasn’t popping out of the front of the thong but I wasn’t having much luck. I shit off the light so I wouldn’t look at myself anymore and checked my phone for messages and whatnot hoping my erection would calm down. Finally after about 10 minutes, my wife began anxiously calling for me.
As I stood up, my erection had almost completely subsided and I tucked it between my legs and opened the door. As I nervously entered the bedroom, my wife was standing there with a pair of men’s jeans on, and a football jersey.
“I thought we could try switching roles for tonight.” She said quietly
“I think that’s a great idea!” I answered
She walked towards me and we began kissing pretty intensely right from the start. As she pressed herself against me I could feel she had something in her pants. My man Dave has a very thick 8” dick so I know what that feels like.
“What’s going on down there?” I asked
“I bought a strap on.” She whispered
“Boys don’t need strap on’s.” I said sarcastically trying to stay in character
“Right, sorry. That’s my dick! Feel how hard you make me!” She said shoving her hips forward and pressing it against me
She began kissing my neck and squeezing my ass cheeks. I was really shocked at how into this was and even more shocked it was her idea! She was really into this!
I had equally gotten into it as I lost myself in the moment and I unbuttoned her jeans and reached inside. I grabbed a hold of a really big dildo! So I pulled her pants down and felt the dildo flop out and poke me in the stomach. I looked down at it and it was really big! Bigger than Dave’s! I found out after it was 10” and thick. It was really realistic feeling too! Had a set of balls and everything!
She pulled the silk teddy over my head and began rubbing my nipples. Then went down and sucked and nibbled on them! I reached down and played with the balls while also feeling how incredibly drenched her pussy was.
I quickly got down on my knees and began sucking on her big fake dick while also slipping a finger into her wet slit. She let out a loud moan almost like she wasn’t expecting it and her knees buckled a bit. As she regained her balance, she put a hand on top of my head and assisted me in sucking her mega cock! It turns me on so much to be dominated or treated like a whore, or just the idea of a man in control of me! Ugh I’m getting all hot thinking about it right now!
“Oh Christ I’m gonna cum!” She cried out as she grabbed a handful of my hair.
I started sucking that dong harder and deeper and fingering her soaked pussy harder and deeper as well. She screamed out so loud that she had to cover her mouth. I felt her pussy muscles tighten around my finger and she damn near ripped my hair out! Once again her knees buckled and she sat on the edge of the bed.
“Get back down there, you’re not done yet!” She demanded
It was so hot seeing this side of her and it made me so fucking hard! So I went back at sucking her big rubber cock and returned my finger to her pussy which was now literally dripping juices. There’s were drops running down her legs, down the fake balls dangling between her legs, and drops just flat out dripping onto the floor. She held me back a bit saying it was too sensitive for more aggressive fingering so I slowly made my way back up to it and before long she was crying out in orgasmic bliss once again. This time she even squirted just a tiny bit. I had never made her squirt before!
“Wow, you’re pretty good at that.” She said
I had no clue if she was still in character or just commending me on my ability to finger her.
“How do you want to finish?” She asked which was what she always asked me when we had sex and I managed not to cum before her.
“I want you to make me your little whore!” I whispered as I stood up
“Really?! How?!!” She asked
“You bought the strap on and dildo, use it on me! Fuck me!”
“I actually already had the dildo, but really?! You want me to put in in your ass?!! Won’t it hurt?!” She questioned
“There’s only one way to find out.” I said as I laid down on the bed.
I was a bit surprised to find out that was her dildo and she’s using a big huge dick to pleasure herself. I’m no slouch at 7” but this was much bigger than me. I tried not to think about it too much though.
“How do you wanna do this?” She asked
“Same as when I fuck you. Put it in me and go for it!” I explained
Seeing that it was her dildo I understood when she decided to put a condom on it. I got up on all fours and she nervously positioned herself behind me. I squirted a bit of lube in my hand and rubbed it on my ass sliding a finger or two in as well.
“I have no clue what I’m doing so stop me if I do something wrong and don’t get mad… are you sure you wanna try this?” She asked one more time
“Mmhmm.” I mumbled as I shimmied into position
She pressed the fake dick against my ass but was super gentle about it and wasn’t getting it inside me at all. I reached back, grabbed a hold of it and pressed it harder against my eager butthole.
“Gently thrust it in and don’t stop until the head is in all the way.” I instructed
She did exactly as I said and in seconds that big thick head slipped inside my asshole. I let out a loud moan and yes it hurt for a few seconds.
“Are you ok?” She yelped
“Yeah, just leave it in there for a second and when I tell you to go, start fucking me. Slow at first though ok…” I explained
I let it sit inside me for about 20 seconds, took a deep breath and told her to push it in a little deeper. Then deeper and then deeper. Before I knew it I felt the fake balls hit the back of my leg.
“Are you all the way in?” I asked shocked
“Yeah, pretty much. I can’t believe you’re doing this!” She said amazed
She started pulling out and thrusting that big thick 10” cock in and out of my ass. At first it was a bit uncomfortable as I hadn’t felt anything like that up there before. This dick was thick as fuck and I felt every little fake vein on it as she slid it in and out of me. Suddenly I the mild discomfort turned to amazing pleasure and I instructed her to go for it!
She grabbed firmly onto my hips and began to thrust. I had to continue to encourage her to go harder and faster as she clearly was worried I was in pain. I kept reassuring her that it felt great, which it fucking did!
After about 10 minutes of her cautiously sliding her fake cock in and out of my whore little ass, I told her to fuck me as hard as she could! She did! I buried my face in the pillow and thought about nothing but cumming! That thick monster was pounding my ass so hard that my eyes began to cry. There was mascara all over the pillow case!
“Stroke my cock!” I cried out
She reached around and as soon as her hand hit my dick I shot hot cum all over the bed sheets. Spurt after spurt of cum kept shooting out of my cock!
“Keep fucking me!” I yelled gripping the pillow and crying into it
Finally the last few drops of cum trickled out of my cock and she pulled that massive cock from my ass. I quickly turned around and ripped the condom off the dildo and began sucking it, once again sliding a finger or two inside her pussy. She was still really wet and sticky and I sucked that cock and fingered her cunt until she started screaming again, cumming and squirting all over my hand.
When we were finished, we both stood at the bottom of the bed staring at the absolute mess we made. There was cum, mascara, sweat and her squirt everywhere! She grabbed the sheets and pillow cases and put them in the washing machine while I hopped in the shower. She joined me and we cleaned up and went to bed. The next morning we woke up and had morning sex, which is the best way to start a day, for the first time ever. It was much more traditional than the previous night but great all the same. I went to work with a sore ass no doubt but I was in the best mood I have been in in a long time!