Sissy's First Boyfriend

For those who have read my previous works Crossdresser's Unexpected First Time, thanks for your ratings! This story has a lot of true components, "based on real events", but is ultimately, fiction.

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Since my first time with a man while I was dressed as a woman, about 2 years had passed. I'm 22 and living in Charleston, SC still and had a few more encounters with men; nothing to write home about. I came to the conclusion during that first encounter that I enjoyed being feminine and so I kept my legs shaved (most of the time), worked out, and regularly used my dildo. When I was home (and sometimes in school - University), I'd keep my butt plug in and lounged around in my femme clothes and in general tried to just be as feminine as possible. Toenails painted, wear a little make-up (that stuff is expensive!), some silky stockings, boy shorts -- whatever felt comfortable. The constant in my life though, were panties. I loved them. I always wore them when I was out, thongs mostly, but love the boyshorts too.

At this point, I'm over 21 and am in full swing of my "club rat" days. I loved the techno/trance scene; the people were all very laid back, open-minded, and there were very few instances of fights breaking out or anything aggressive and off-putting really. The other nice thing is that it's completely normal to dance alone, just enjoying the music and scene. Not to say that I partook in any of the drug scene stuff, but maybe, I dabbled a little bit. E was the big thing back then and coupled with the soft panties, no body hair, and being surrounded by a bunch of people who understood what you were doing (as they probably were also), it was amazing.

So one night, I'm at the club and I'm wearing normal (guy) clothes, with the exception of my black mesh thong. I'm dancing, drinking, maybe a little more..., but I'm having a great time. There are a couple of guys nearby who are also dancing and I had caught the eye of one of them a few times. At the time, I didnt think anything of it, but I did notice he was decent looking. However, chances are good that he's not into guys, so I just kept having fun. Soon enough, my intoxication is really kicking in and I move over next to this steel post (it's a club that's set up like a warehouse, you know what I'm talking about), to take a breather and recoup. Next thing I know, the Decent Looking guy is next to me. I'll call him Jake.

Jake comes up next to my ear and I can feel the heat from his body and the breath on my ear and I instantly started tingling all over. With a very knowing smile, he offered, "you look like you're enjoying yourself, I'm ........"

I responded, "I didnt catch your name, but its okay, I already made up something for you when I saw you dancing out there." At this point, again, I'm intoxicated and I just decided to let my flag fly. Besides, who has time for games and BS?

"You made up something for my name huh? Well it sounds like I caught more than just your eye out there. Any chance you want to party a bit more after this place closes down?"

"Just you and me or your friends as well? Because to be honest, I dont think I could handle all that, even in this state." There. Even if he was just being nice, or was just going to offer me drugs, or a drink or whatever, there should be no confusing the situation.

He laughed and smiled a pretty decent looking smile and just responded with, "No friends...but I doubt they would say no if you offered."

Normally, I dont invite strangers to my apartment. We meet at a hotel or a parking lot, or their place and that's it. But frankly, I was getting kind of tired of that. I wanted something slightly more concrete, not to say that I wanted to come out of the closet, but finding guys online had become tiresome and redundant; most flaked, the ones that didnt were typically lying about something...etc. I wanted a friend (with benefits...lots of benefits) with whom I could be open with and not have to come up with cover stories, BS or anything. Just...free.

We danced a littlel bit, i just naturally took up the position in front, with him behind me and it's coming up on 3am, which is usually last call for the place I was at and so we exchanged numbers and he went on his way. I on the other hand, decided it was time to leave and so I went outside and caught a 10 minute cab ride back to the apartment.

As soon as I got home, the plug went in and some more sissy hypno was turned on. I was already freshly shaved (who wouldnt on a Friday night?). After about 20 minutes of edging myself, I was invigorated. Still had the fantastic buzz, but I wasnt tired at all. So I pulled out my phone and sent the near desperate text: "if you're still up, here's my address."

I received a response about 5 minutes later telling me that he would be there in 30 minutes.

At this point, I flew into action. Straight to the shower, 5 minutes there to wash the smoke and club smell from me, and then it was on to picking my outfit. I didnt put anything on, but I laid it out. I figured I would let him know that I was 100% bottom and that I liked to dress the part when he got here. If he wasnt cool with it, well, I can get fucked while naked also.

I picked out my black slutty heels. I love these. 6 inch heel, open toe, 1 inch platform at the bottom and a single strap across the toe and another around the ankle. Simplicity at its finest. A tight little black dress was next, coupled with a brown wig, some black fishnets and my cute silver butt plug (slightly larger than my normal one) to top it off. Yes, I love the slut look. What sissy doesnt?

I hear the knocking on my door and I get that taste in the back of ones throat where you know the taste of cum is close. I'm wearing just a smile and he slides in coolly, with a quick elevator eye up and down before closing the door behind him. As he moves towards me, I hold my hand up to stop him and say, "before we go forward, I want you to know that I'm a total bottom, I dont fuck, I get fucked and I love dressing the part."

For a split second, he's speechless and I get that nagging feeling of "maybe I fucked this up." Thankfully, he responded quickly with, "then why arent you dressed? Did you think I was going to blow you off?"

I stared back for half a second before almost running back to my room and saying, "5 minutes. Get comfortable." After which, I hurriedly put on my stockings, dress, fixed the wig in place, threw on a little make up (eyeliner and lipstick -- cherry red = dick sucking lips) and threw my heels on. As I walked out, strutting, his jaw dropped. And then the pants dropped.

As I start moving my eyes up and down him, I see a nice average sized cock, nothing big, but its definitely thick. As I continued strutting towards him, he sprang from his seat on the couch and pulled me close. I've never actually kissed a man before. It was always just business. But this, his lips, his frame, everything, I just melted into his arms. He asked me to stay put so he could look at me and he took in everything. I dont think an inch of my body went unnoticed by him. He put his arms around my waist and pulled me on top of him, falling to the couch. This is what it felt like to be a girl, and I was loving every minute of it.

After a good 20 minutes of just making out and me grinding on his cock with my ass, he took his hand on my head and started pushing me down. I knew what was coming and I just looked directly in his eyes, made my way down and took that head right into my mouth. Didnt break eye contact once.

I'm working his shaft with my hand, working the head and a little further with my mouth and then I take his balls into my mouth. Licking them, smelling the musk, taking it all in and thats when I hear him moaning like he was going to cum. Thankfully, he didnt. I had other plans for that beautiful cock I was making love to. After a few more minutes of me sucking, he began to get really into it and just shy of being aggressive. Not in a bad way, but the sexy, rough way that all girls like every now and then. This was definitely one of those times where I was into it. He stood up, spun me around and pulled my dress up and panties down in one fluid motion. Like hes definitely done this before.

I was just about to stop him and grab the lube when I felt his tongue pushed into my hole. It was amazing. i'd never had this done before and I think that action alone made me feel like more of a woman than I'd ever felt before. He was going down on my pussy and loving it. As he got more into it, I got more into it. The feeling of what I was doing and wearing, mixed with what was happening just put me into sensory overload and I just had to have his cock in me.

"Put your tongue away and push inside of me already!", I cried out. He stood me up against his body, him behind me and me jerking his cock and I just turned my head and kissed him full on the mouth. I've never been an ATM kinda person, but I didnt care at this point. He pushed me away and down on my knees. I felt the familiar cold of the lube, followed by the unmistakable head of a cock right on my entrance.

I noticed he didnt have a condom, so I quickly asked if he was okay, which he politely said yes, but if it made me more comfortable...I quickly declined. "Fuck me already with that big cock of yours" with a small wink. That did it and soon he had me moaning like a bitch in heat. Personally, I love doggystyle. It provides that ability to just get fucked, feel like a cheap slut and, you dont have to make eye contact! In this case though, I wanted to look upon him. So I flipped over and put my legs up on his shoulders. All I saw was a hot guy, with a great body, pushing into me and making me feel amazing. All of this and I was leaking like crazy, it had been a while since I'd came hands free, but tonight was looking good!

"Tell me baby, where do you want my cum" he said softly. I didnt hesitate, "fill me up baby, I want to feel you inside me all night". About 30 seconds later, he was making short, quick thrusts into me and then he lay on top of me, pinning me down to the bed and I felt his cock twitching inside of me. He came A-LOT. After another 30 seconds of him filling me up and holding me down, I could feel the heat of his cum spilling out of me. I didnt realize how much until I saw the spot we had made. "I'll change the sheets tomorrow, tonight I'm going to relish it", I thought.

As he got off of me and slid his cock out of me, I felt the sweet sensation of cum dripping down my leg as I stood shakily. He looked down and then back up at me, kissing me full on the mouth again, he said, "the smeared make up, the cum down your leg and how hot you were fucking...I want to do this again."

"Here's the deal. I'm going to be back over here tomorrow, and the night after, and more after that. But I want to come over to my girlfriend. Thats you. I'll bring you some clothes, but in the meantime, go get more. I want to see you as a girl 24/7 sweetie. Tomorrow though, I want to see you cum. Until then...". He kissed me again and left.

So. I had a boyfriend and I was officially a gurl! We had so much sex. Even went out a few times at night together, me dressed of course. This went on for a little less than a year. The hottest year of my life.

I didnt cum during sex with him, but as soon as he left, I slipped out of the rest of my clothes, and pulled out my butt plug, I was hell bent on keeping his cum inside of me. Then I went online to do a little shopping for my new boyfriend. More heels, some lingerie, a few sexy dresses and panties. Oh so many panties! After that, a few basic girl clothes, pants and T's; after all a girl needs outfits for anytime right? I desperately wanted to cum, but something told me to hold off for tomorrow. I'll just stay horny and worked up until then. Good thing it was the weekend!

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If you like this story, I can post a few more about our fun times together, so like and comment if you want more! Hope you enjoyed reading as much as I did re-living this experience!