My journey into hedonistic crossdresing, Part 1

Part 1 deals with events that had transpired which lead to my first sexual encounter with a man, and ultimately, my first relationship as Elaine. Almost impossible to believe, and the thought of Vince, even today, still makes me yearn for those wondeful days! The ending is where you'll find the sex part, if you need to jump ahead!

At 6 months shy of my 19th birthday, I had just discovered that I wasn't the only "whack job" on the planet! Before the internet and broader social acceptance, it was pretty hard to be a crossdresser, transvestite, drag queen, etc...especially being from a very small town.

It took a bit of doing, but I'd worked up the courage to enter an adult bookstore in mid town Manhattan....42nd street area, years before they cleaned it all up. My heart was pounding and racing, I was half scared senseless and extremely excited at the same time. I won't go into a lot of detail here, but saw my first transvestite contact magazine, and, my very first shemale, Sulka,
in peep video. Needless to say, incredibly hot as I wasn't sure whether I wanted to "be" her, and being pleasure by hot, hard thobbing cocks, or, to "do" her. It would be about 3 months and I would find out.

About 3 months after my "discovery", I was dying to get away from the base and go someplace to explore my feminine side. I'd been secretly dressing since the age of 10, and it's been about 9 months since I've been able to dress in anything. It's been almost as hard being able to masturbate for god's sake!

I decided to get off the base for a few days, put in for a long weekend, and thought I'd get away from the NYC area and head home maybe. Really undecided, but had to go somewhere. Saturday came and I put a small bag together and headed up to Grand Central Station, where I'd planned on getting a bus ticket and heading home to upstate NY, about a 4 hour bus ride. I arrived at the station around 1pm, and the earliest bus out was at 4pm.

I went to a little pub located inside the station, got a draft and a plate
of fries and sat down at a small table. Looking around, there was only a couple of other people in the place, not much at all going on. As I ate my fries and sipped my beer, thinking about how long a wait I would have, an older gentleman approached my table. he was dressed in a suit and tie, with an overcoat on. He introduced himself as Vince Capetelli, and asked if he
could join me for a drink. I was caught off guard, but was polite and said

Vince was a very personable guy, shared some of himself and got me to pretty much spill out everything about me, not anything gender related or sexual, but everything else. He indicated that he was going to pick up his nephew for the weekend, who, as it turned out had been called in to work and had some technical emergency and wouldn't be coming. He had an hour and half drive out to Long Island and thought he'd stop for a drink before heading out.

What transpired next totally shocked me. Since I'd indicate I wasn't certain about going up home, or maybe doing something else for my long weekend, he'd invited me out to his place for the weekend, or just a day or two. He'd already gotten extra food, drink and such and it would be a shame for it to go to waste. He had a game room in his basement with a pool table, darts, etc and was sure I'd find something to entertain myself with. With almost no hesitation, I accepted his offer!

The 1-1/2 hour drive flew by. I wasn't certain, but thought that Vince was seducing me. And while I had really wanted to find a way to dress over the next couple of days, my desire to explore sex with men was strong enough to see where this might lead. Vince practically talked my ear off on the drive, but he had a way of captivating an audience, I guess.

We arrived at his beautiful, 4 bedroom, 4 bath seculed home at right around 3:30 in the afternoon. A cold, blustery February day, but inside was very cozy. A well furnished home with a very homey type atmoshpere about it.
Vince suggested we get me settled in first, and gave me my choice of 2 rooms.
The first, just a fairly plain room with the usual accoutraments, bed, bureau,
closet, etc. The 2nd, a very feminine room, which turned out to be his ex-wife's daughters room. Out of the house several years now, Vince said he just hasn't had time or the concern to make changes yet.

This room had a very feminine flare, pastel wallpapering, matching bedspreads, lampshades, etc. The dresser's were also matching, a vanity with a large mirror, a full, floor length mirror, a huge walk in closet and a private bath, complete with a bidai. As Vince showed me the room, we went into the closet which still contained a large amount of women's clothing. Dresses, skirts, formal gowns, heels, etc. Vince swooped his arm into the rack on the right side of the closet, pulled out an armfull of dresses, and mentioned something about after the divorce the ex just left a ton of stuff behind. I became transfixed on the armload of hear just skipped a beat at what was racing through my mind. As Vince let the dresses fall from his arm, I couldn't help but keep my eyes transfixed on them. I'm sure he noticed my lingering look, and, the fact that I'd turned a couple shades redder with embarassment! The bath had an oversize tub, a larger shower, all sorts of luxuries, better than about anywhere I'd ever stayed.

I said this room will be just perfect! I mean it'll be fine...just fine...just fine thanks, trying to cover up my initial enthusiasm. Vince told me to drop my bag in the closet, and then e****ted me down stairs. We toured the house, he made us both a drink (Gin and tonic, which I still enjoy today!).
We chatted for a bit and he suggested I help myself to taking a shower, etc while he went and got out of his suit and into something comfortable.

I quickly jumped at the chance to be alone with that incredible closet.
Vince hadn't made any attempt to make a pass at me, and I thought maybe he wasn't gay after all or maybe he just isn't into me? I entered the room and closed the door behind me. Immediately went into the closet and began checking out all the skirts, dresses, gowns. OMG...this was flipping amazing!
I pulled my shoes, off, took off my socks, had my pants and shirt off in no time.

I'd left my underwear on, as, I would be slipping into one of these dresses and didn't want to stain any with precum. I pulled what looked like a prom dress off the rack. Slipped it off it's hanger, unzipped the back and checked the size. It was a 14...a bit large for me, but stepped right into it, pulled it up, slipped my arms through the spaghetti straps, reached behind and zipped myself into the luxurious satin. The bodice was snug after all, and the skirt just billowed out all around me, heavy and amazingly sensual!
It was a pale blue, and ultra fem, god it felt so amazing! My cock had already started to swell, and I couldn't help but grab it through the fabric of the dress and massage it slowly. I was so incredibly horny, I thought I might explode right into the dress! I just had to see how I looked and stepped out of the closet and in front of the full length floor mirror. I started to masturbate furiously over how hot my ass looked in this dress, just how fuckable it was, and how much I'd love to be getting fucked right now in this incredible gown!

I dropped down onto my knees and sat back on my ankles, and played with my cock. Time must have really gotten away from me and next thing I knew, Vince came walking in the door, asking if everything was OK and then just stopped cold in mid sentence. I hand with a pile of gown wrapped around my raging hard on, kneeling on the floor in a prom gown that belonged to his step daughter!

Well, Vince began, I hadn't anticipated finding this at all. I'm sure this has got to be quite emabarrassing for you, now doesn't it? I stammered, and rose to my feet, my cock tenting the skirt of the dress, and me, trying to hide it with my hands. I'm spewing out I'm sorry's, I'm so sorry. I'll get me things and leave quickly. I'm so very sorry. Vince cut in and began assuring me he was not at all upset. Surprised, but not upset. He began explaining to me, exactly the things that I'd been through since I started cross dressing years ago. The feeling of isolation, guilt, shame, etc. He
then told me that he could help me get beyond all those feelings, and allow the person I was inside, come out, and be fully expressive, with him. I didn't know what to say. He moved close to me, put his arms around me and just hugged me. He pressed his thigh against me, rubbing against my now semi-erect cock. I tried to ease myself away, as the feeling was making my cock hard again and was afraid of him noticing.

He eased me backwards, to the edge of the bed, and guided me to sit down. He was dressed in an old pair of loosely fitting sweat pants, and a t-shirt. He was overweight, probably 50 pounds or so...with a gut. About 6 feet tall, probably 260#'s or therabouts. Balding, not really anything you would descirbe as a hunk. Just sort of a pudgy, older man.

He looked me right in the eyes, and spoke softly. He told me to reach under the waistband of his sweat pants, and pull them down to the middle of his thighs. I dint' move a muscle at first, my mind was racing and I had no idea of what I should do. Part of me wanted to run, the other, to do as he said. He reached down, grabbed my wrists gently, and pulled my hands up to his waistband. I eased my fingers inside the waist, and slid them half way down his thighs. He had no underwear on, and his cock was already 1/2 erect.
It had a farily large head, bigger than mine, and hung almost 6 inches or so, 1/2 hard. Vince began speaking softly, telling me to reach out, to touch his cock, to feel it, fondle it, as I've wanted to for such a long time. I let my hands drift to his cock. My heart was pounding out of my chest. My cock was hard again, aching to get out from under the confines of my underwear.

I took his cock into my hands, lifted it up slowly, and looked at it, intentely. This is the very first time I'd ever looked at another man's cock, felt it. I could literally see and feel Vince's cock get hard. It began to swell and stiffen right in my hands! Vince kept speaking to me, softly, telling me what a natural I was, how wonderful I made him feel by touching him. He begain to coax me into tasting him, to lick his cock, to see how it feels on my tongue. He leaned in towards me and, with his cock point straight at me, I leaned forward and went to touch the tip of his cock with my tongue and it pulsated, hard, upwards, almost scaring me! Vince laughed briefly, made a comment about how much his cock was thrilled about going into my mouth! Again, I went to touch the tip of his cock with my tongue, and made contact. The soft texture of the head, the smoothness of it. The scent of Vince and his manhood, all almost intoxicating. He kept speaking, telling me to take him into my mouth. Feel the pleasure of pleasing a man orally.

I did just that...I took his cock into my mouth...I was swooning. I was excited, aroused, unlike anything I'd ever experienced erotically. I had no idea what I was doing, I was just doing what felt good to me. I was far from deep throating him, but was sucking in about 5 inches of his thick, hard 8 inch cock. He continued to speak softly to me, telling me how wonderful my mouth felt on his cock. How much it turned him on to see me with his cock in my mouth, in this beautiful dress, doing what was seemingly so natural for a "girl" like me. Just at those words I thought I would erupt right then!

Vince pulled his cock from my lips and backed away. I looked at him, puzzled and with a lust crazed look...wanting his cock back between my lips.
Vince pulled me to my feet, ran his hand down my back and onto the crest of my full, round butt. He guided me to the bathroom, taking me to the shower.
I want you to prep yourself for me, dear. That bag on the wall is to cleanse yoruself, inside. I want you to take an enema and prep for our evening. You don't have to, mind you, but trust me dear...I know this is what you've been longing for.

98% (28/1)
Posted by elainetgrl
3 years ago    Views: 615
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9 months ago
loved it so much , amazing got so hard thank you .
9 months ago
great story if it is true hun
1 year ago
Very well-written! Would love to help a young lady find herself like this
1 year ago
Oh WOW !
Very hot story Elaine, so erotic!
Cant wait to read part 2 :)
2 years ago
Great story. Can't wait to read the other chapters
2 years ago
Fantastic story.
So much of the first part I emphasised with. So much of the ending I was simply excited with.
Thank you for sharing
2 years ago
Great story! Thanks for actually using paragraphs as well, it's hell reading run on stories.
3 years ago
Wow fantastic would have loved tobew ther thanks
3 years ago
OMG..I'm so hard. Please tell me this is a true story.
3 years ago
Great story/beginning. I think alot of gurls have been here. Thanks baby
3 years ago
Great story!
3 years ago
Hot story!
3 years ago
Tyhanks i got so hard i just jsacked off all iover everything thanks again
3 years ago
"my cock tenting the skirt of the dress"

I LOVE getting a hard on in my dress.

is this a true story?