First Gay Crossdresser Experience

by James

What’s your gender? Man
How old are you? 40
What’s your race/ethnicity? Hispanic / Latino/a
What continent do you live on? North America
What country and/or city do you live in? USA
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Welder
What’s your current relationship status? In a serious relationship (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Mostly heterosexual
Any other term(s) that describe your sexuality or sexual identity? Bi-Curious
How many sexual partners have you had in your life (including oral sex)? 25
How many hookup stories have you here posted before? 0

First Gay Crossdresser Experience

How long ago did this hookup happen? 3 years

What was your relationship status at the time? Single

How would you best classify this hookup? Short fling

How long did you know the person before this hookup? For less than 6 months

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? I was recently divorced and casually dating women. During this time, I decided to indulge a major fetish I have for pantyhose and occasionally cross dressing. I spent the summer buying pantyhose, lingerie teddies, heels, dresses, bras and panties, wigs and makeup. I would dress at home and take pictures, occasionally going out in public fully dressed or wearing pantyhose under my jeans. One of my favorite things to do was wear pantyhose under my jeans with a butt plug in and go to happy hour at a restaurant near my house. I would chat with guys and feel like a little slut. Since I was taking pictures all the time, I decided to start an Instagram page and post pictures of my legs and body but not my face. This particular gentleman sent me a DM and we started chatting for about 5 months. He also was into crossdressers, had a huge pantyhose fetish and wanted to be with a man.

He was about 10 year younger than me and Hispanic as well. We chatted and he was very sweet and had also never been with a man, but wanted to try. We exchanged pictures and he was cute and again, very nice and not pushy. If we decided to go through with a sexual experience we agreed I had complete control and could back out at any time. He worked close to my job, so meeting him would only take a 10 minute drive, but it would be to see if we both felt comfortable before proceeding. The day before we were going to meet I shaved my legs completely (I hate hairy legs in pantyhose) and got a French pedicure. After work the next day, i stayed at the office until everyone was gone and put on a pair of Leggs Suntan pantyhose, small jean shorts under my jeans and headed to his job at Walmart.

Although we exchanged pictures and I knew what he looked like, he had only seen pictures of my body. I parked a distance from the entrance and walked into the store. I texted him that I was there and he told me he was in electronics which is fairly empty. He was about 6 feet tall, not stocky but not thin either, bald with some nice stubble. As we talked, he was being kind of shy and blushing a bit and it was sweet. I asked for some help locating things and made sure to bend over and give him an ass shot. He was off work in about 10 minutes so I told him to meet me at my car afterwards.

He came to my car and I asked him if he wanted to see what was under my jeans. He sheepishly said “Yes”, and I removed my jeans and shoes and placed my pantyhose legs across his lap and told him to massage my legs and feet. I was immediately horny as hell as he caressed my legs and feet. I could also feel his hard-on in his work pants and encouraged him to keep rubbing my legs and go higher up my thighs. He did as instructed and slipped his hand inside my jean shorts and gently rubbed my cock.

At this point, I had to stop as I was getting turned on and enjoying this attention, but he couldn’t stay with me that night because he had to take care of his grandma. I also arranged this meet-up and “touching” session to see if I enjoyed attention from a man, he was up for the cross dressing experience, and he was the “right” person for my first gay experience. We agreed to meet the next night at a hotel airport and we would spend the night together.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We met at the hotel bar and had a few drinks. After again discussing sexual history and getting to know each other, I excused myself and went up to the room, which was a two room suite with lounge chairs, couches etc. I went upstairs and did the full makeup, wig, nails, fake boobs and put on a pair of suntan pantyhose and a red thong teddie paired with a white silk robe. I felt beautiful and feminine and couldn’t wait for the experience!

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? He entered the room, told me I was beautiful and we kissed immediately. The kiss was slow, wet and deep. I wrapped my arms around his neck as the kissing became more passionate. He moved his hands to my ass alternately squeezing and caressing as the kisses became wetter and deeper. I was in heaven and his raging hard on pressing against me.

He pushed me against the wall, undid the sash on my robe and opened it up to reveal my red teddie. He dropped to his knees, kissing, caressing and licking me all over while moving his hands up and down my legs. At this point, I was hot for him and I was about to give my first blow job. I dropped to my knees, undid his jeans and out popped this beautiful 6″ cut cock with just the right amount of girth.

I was in awe at first and curious as to what he would taste like. I wrapped my hand around the base and took the head in my mouth, swirling my tongue up and down while stroking his shaft. My other hand on his balls, caressing them and then sucking them gently. He was moaning and went into overdrive when I went under him and started tonguing his ass and then moving back to sucking his cock.

This goes on for about 10 minutes and I’m getting into it and talking dirty to him asking him, “Do you like the way I suck your cock?” and “Are you ready to cum in my mouth?”. Honestly, I was furiously sucking his dick like it was the first and last blow job I was every going to give. I was possessed! He announces he’s going to cum and I’ve already decided I’m going to swallow, plus there is a beer on the table within reach to wash it down. I feel his cock start to pulsate and he shoots his cum into my mouth and I hungrily swallow it all. It didn’t taste good or bad which I was happy with. Afterwards, I gently lick his shaft and head to clean him up. He’s still partially dressed, so he strips naked and sits in a lounge chair while I mix him a cocktail and he recovers.

I strip off my robe, hand him his cocktail, and sit on his lap. He has a wrestler’s body, so he has muscles and was very fit when he was young, but has a little meat on him which looks good. I play with his bald head, run my hands on his chest while he caresses my pantyhose legs and we sneek some deep kisses. After about 10 minutes, I can feel his cock getting hard and ask him if he’s ready. I get off his lap, he stands up and we embrace and begin kissing passionately again. Our hands are all over each other as the pace picks up and again I drop to my knees to begin blowing him to get him ready.

After about five minutes we move towards the bed and he announces that he wants to make love to me, grabs my ass and lifts me up, I wrap my legs around him and he carries me to the bed while our tongues dart in and out of each others mouths. He gently lays me on the bed as we feverishly keep kissing, my hands finding his ass and I am way ready for this.

I tell him that I want to stay dressed because it turns me on, so he unsnaps the teddie at the crotch and after a few tugs, rips open the pantyhose revealing my cock and hungry asshole. He starts sucking me off and it’s glorious, licking the head, tongue swirling up and down the shaft and stroking me, but I want more.

After about five minutes, he stops and removes the butt plug and starts applying lube to his cock and fingering my asshole to get me ready. At this point, while I only met him recently, we’d been chatting for about 5 months, so I implicitly trusted him and wanted him raw in my ass. He pushed his cock to my asshole and starts working it in slowly. Once the first couple inches are in, he slides in and out of my ass with ease and plenty of lube. We start with my legs on his shoulders as he sucks my toes and strokes my cock while going in and out of my asshole, then move to missionary with lots of kissing and caressing. It was fucking hot and like I was in a dream.

We switch to me on my side as he enters me with ease, squeezing my ass and telling me how beautiful I am. We move to doggy for a few minutes and then back to missionary where I come right away and after a few minutes he cums deeps inside me, his cock pulsating. He stays on top of me kissing me and telling me I’m hot and I can’t describe the feeling because it was about more than sex. After he goes soft, I feel his cum drip out of my ass, we roll over with my arm across his chest and we fall asleep.

We wake up the next morning to smiles, quickly shower and I blow him again and swallow. I get dressed for work and leave while he stays and sleeps until check out time.

I was on cloud nine all day and thrilled that I got to indulge my cross dressing and be with a man in one night. He was perfect.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? I was going through a divorce at the time, so this type of attention and living a fantasy was just exactly what I needed after being in a sexless marriage for years. I wasn’t going to miss out on anything while being single.

We continued to see each other for another six months, but he would come to my house and stay the night. The routine was dinner and drinks then back to my house for role play. I would be a lonely housewife, real estate agent, etc and he would seduce me. I would wear skin tight dresses, lingerie, heels, short shorts, pantyhose, heels and anything he wanted. He also let me fuck his ass during this time, which I thoroughly enjoyed.

I became very fond of him and we are friends to this day. We both are in a relationship with women, but will talk about old times and possibly hooking up again when we’re single.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Condoms

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Thought it was an important experience to have, Submission / Relinquishing power

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? Just this page

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? Living the fantasy of being with a man, the cross dressing and feeling feminine, the romance and pleasure he brought me.

What was the WORST thing about this hookup? nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I have always been open about sex, but being with a man is something I will cherish forever. I also believe a person should experience everything. After my divorce I indulged in anything that made me curious. I wore women’s clothes, masturbate in pantyhose, use a dildo on myself, been pegged, eaten ass, sucked cock and been fucked in the ass. I am thrilled to have experienced all of it.

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? Not at all negative

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? Life is too short to not have every inch of you sucked or penetrated.

What do you think about the Casual Sex Project? Love the page

You have a hookup story to share? Submit it here!