This is a true and original account of one of my many naughty escapades as a crossdressing slut.
At 33 years I have been a crossdresser now for over 20 years. Although I am bisexual and enjoy sex with both men and women I have a definite preference to being dressed like a perfect slut and getting drilled by some handsome hunk. Having just ended a long time relationship with a woman my hunger for dressing-up went unfulfilled for several years. I seem to be making up for lost time by dressing every chance I get and cruising the bars and the internet for willing partners. I dress and act like a whore in tight short skirts, high heels, stockings and tons of slutty make-up so attracting willing partners is as easy as attracting flies to honey, and I am loving it!
A few months ago I met a good looking black man that responded to my ad I posted on a transgender message board. He lives in Chicago and said he would be visiting Houston on a business trip soon and was hoping we might get together. He sent me several pictures and he was quite good looking. Frank is very tall, great body and nice smile. Although I had been with several CD's, couples, and guys, I somehow have never hooked up with an Afro-American. I think black guys are extremely sexy but it just never happened for some reason. Frank was in his late thirties or early forties I guessed and he was divorced. He scared me just a bit with the pictures he sent me of his cock because he was rather large. (The legend is evidently true!) I guessed he was about 8-9 inches long but fortunately not too big around, but still above average. We emailed each other over several weeks then we exchanged phone numbers and he called me almost every day. The chemistry between us was great. He was very sweet and a perfect gentleman and of course we would end each call by talking dirty to each other, and that was a real turn on for me.
Finally Frank's business trip was booked and he was headed to Houston. We made plans to meet at a local club that caters to the gay/TG crowd and if we both agreed we could party over at my place just a few blocks away. I took the afternoon off work and begin my preparations early with a glass of wine and a long hot bath. While I was in the tub the phone rang but I decided to let my answering machine take the call. It was Frank's voice and he said he hoped that I would not be upset but at the last minute a business associate of his decided to join him on the trip. He didn't think he could just leave him in his hotel room that night so he would have to postpone our much anticipated rendezvous. Damn! I was really looking forward to fucking Frank tonight! I called his cell phone back immediately and he apologized profusely. He was obviously disappointed also. I said there might be a way, if... Frank seemed confused for a minute then he picked up on where I was going.
"So you want me to ask Ty if he wants to join us?" he said. "Uh-huh" was my reply. "Are you sure?" "I think it might be fun" I whispered "I'll call you right back."
Not more than two minutes later Frank called back with excitement obvious in his voice. "We will see you at 7:30 hon." "Great"
I returned to my vanity to prepare for what promised to be an interesting evening. First thing I did was to lube up my butt plug and place inside me. I find this stretches me for sex, not to mention the tingly feeling it gives me while it's in. Next my panties to hold it in place then my robe while I apply my make-up. I did my usual slut make up with eyes lined in black, long false lashes and tons of mascara. I lined my lips with a dark red pencil outside my natural lip line for that full fuck-my-mouth look, and then filled it in with several coats of bright, glossy red lipstick. I poured another glass of wine and relaxed with a smoke at the kitchen table for a few minutes. I just enjoyed that wonderful feeling of anticipation for a great evening ahead. By wiggling my ass when I sit I can move the butt plug in circles in my she-pussy and feel a great warmth overtake me. Mmmm,I just love being a gurl!
I selected a sexy black and white stripe mini skirt to wear with black stockings and a black blouse with an open collar and French cuffs. I put on my big blonde wig and teased it out, then squeezed into my black high heel pumps. Admiring myself in the mirror gave me second thoughts about going out like this. I was a bit tipsy from the wine and I looked very intensely sexual even for me! I called Franks cell phone and asked if they would rather come over to my place than meet at the club, and after a very brief consultation with Ty they agreed and I gave Frank directions to my place.
I set up my camera and took a few pics of myself as I finished the bottle of wine I had opened. I delighted in wiggling my ass into the chair to stimulate my ass pussy and applied a few more coats of mascara and lipstick as I waited for my new lovers to arrive. At exactly 7:30 I heard two car doors slam and a few seconds later the doorbell rang. I was standing at the door looking out the peep hole but I counted to 20 before I opened it, not wanting to seem to anxious, even though my heart was pounding in my chest!
Frank greeted me with a hug and a peck on the lips then introduced me to Ty. Ty is a bit heavy set and medium height, shaved head and a big smile that seems to take up his whole face. When we hugged I couldn't help but feel his boner as he pressed up against me. (I like that in a man!) I could tell the guys had been drinking too, so we just seemed to glide into a conversation most of which was about what a hot little `ho I was.
They had brought us three bottles of champagne (!), so Frank and I headed to the kitchen for glasses as Ty settled in on the couch. In the kitchen Frank quickly grabbed me and kissed me. I felt for his cock and sure enough his too was at full attention. We kissed for several minutes making a mess of my lipstick all over both of our mouths. Ty called out that it was awful quite in there and that broke our spell. I asked Frank to open the wine and pour us each a glass while I retreated to the bathroom of fix my lipstick.
When I returned to the living room the guys were seated on the couch so I squeezed in between them and Ty handed me a glass of champagne, and proposed a toast. "To the sexiest `ho in Texas" said Ty "I'll drink to that" said Frank And in one big gulp we all downed our champagne.
"Now let's get this par-tay rockin' girl." Said Frank, as he stood up and unzipped his trousers.
I reached for Franks boxers and pulled them down revealing his well endowed cock. Frank slapped it on my face a few times and I was able to guide it into my hungry mouth. I immediately felt it swell in my mouth as I sucked the huge head. Frank placed his hands on the back of my head and slowly and rhythmically fucked my red lipsticked mouth, as I sucked him.
Ty was watching from inches away, apparently fascinated by what he was watching. I squeezed Frank's balls tight with both of my hands as he fucked my mouth. I wiggled my ass into the couch pushing my putt plug deeper in my pussy ass. "Whip it out Ty and fuck this ho", said Frank "Mmmmph.mmfuckmeTyy", was all I could manage to say with Franks black dick in my mouth.
As Ty removed his pants I guided Frank over to the coffee table and he sat down on it. I slipped down my panties squeezing my ass cheeks to hold in the butt plug. Is I lifted my leg to slide my panties off they got hung up on my high heels. I lost my balance and grabbed onto Frank to keep from falling. I had hoped I could discretely remove my butt plug so the guys wouldn't see it, but shifting my weight that way caused me to unclench my ass cheeks and the red rubber butt plug literally shot from my pussy ass and bounced twice and rolled across the floor. I was mortified at what had just happened
"What the hell is that?" Ty said. Total silence for a few seconds then realizing what that was, we all broke out laughing!
It didn't do much for the sexual tension but we all had a good laugh about it and we had a chance to have another glass of champagne and I fixed my lipstick again before we resumed our fuck fest.
This really was fun being with two great guys like Frank and Ty, They were great lovers, good looking and just fun to be with. Ty wanted to feel up my ass so I got down on all fours and he fingered my pussy ass. Since I stretched my pussy with the plug and lubed it real well, Ty had no problem getting three fingers inside. I love to be fingered like that and begged Frank to fuck my mouth again. He slid over and put his cock in front of me and teased me with it. The musky smell of his hairy balls and the head of his cock just touching my lips took me to another level. I don't even remember when Ty replaced his fingers with his cock but he was now ramming me deep with his black pole. This is certainly the time when a girly boy feels so 100% female..when a guy; in this case two guys are using you for their exclusive sexual pleasure! By now both guys were fucking away. Ty in my pussy ass and Frank deep down my throat. Both guys were telling me what a slut ho I was but it sounded so distant and far away to me. I felt like I was in a trance. Ty began bucking first and I knew he was close, I met his thrusts and wiggled my ass like guys like it. Ty stiffened and rammed me hard as he shot stream after stream of his hot cum in me. I was so wet and open and full of air that when my ass pussy farted, (and we all fart after ass sex), it squeezed cum down my legs and on my shaved balls. Frank pulled his cock from my mouth, got behind me and took over Ty's position fucking my ass. It slid right in but Frank was longer and it hurt a bit. I knew I needed him to shoot quickly so I did my ass wiggle and sure enough Frank shot his hot spunk in my ass. I swear he shot at least ten or twelve loads and it seemed to last a forever. After Frank pulled out of my pussyass I stood up and I felt their cum ran ooze out of me and run down my legs. I love that! My legs were wobbly, my ass hurt and my jaw was sore from giving blow jobs, but I loved the feeling of pleasing my men! Ty and Frank collapsed on the couch and I headed to the bathroom to clean myself up. Still turned on and now alone in the bathroom I masturbated myself to a powerful orgasm using their cum as lubricant...mmmmm, feels so wonderful to be a nasty gurl!
Lots more sexy experiences to share if you are interested.. XXOO Sandi Lee