After my divorce I found I had some time to indulge in my many fetishes and fantasies. Those being; cross-dressing, smoking 120s and man to man sex. None of these were a factor in my separation however. It wasn't long before I was on line ordering lingerie and shopping locally. This has been going on for sometime now but always on the sly and rarely. I had accumulated a large assortment of sexy, slutty lingerie that I would dress in 4 to 5 times a week. I have 4 garter belts, 10 pairs of lace top seamed stockings, a few thongs, several bras, a bustier and a corset. All of them are white or black. As my passion for this grew, so did my interest in developing my female persona, Jill. I purchased a wig and 3 pairs of 6 inch + heels even some opera gloves. Everything is white or black.
My routine was basically this; I'd get home from work, shower, and shave my legs, armpits, balls and tant. Then I'd spray on some perfume and dress. I'd start with stockings, fasten them to a garter belt, corset or bustier, stuff my bra with stockings then put on the wig, shoes and finally the gloves. Next, I'd light up a Max 120 and begin my porno -- chat room internet play. I had also bought a rather large life like dildo with a suction cup and would practice sucking dick with it. It was big, 10 in long and 2.25 inches in diameter. I would always smoke a 120 in front of a mirror with the dildo secured to the wall. I have this ability to ejaculate most of my cum without having an orgasm. When I felt cum starting to release, I'd place my cock over the dildo and let my sperm flow onto it. Then I'd spread it over the rubber cock with my lips and suck my cum from it. I absolutely love the taste of my semen and I would lick and suck it while I tried to deep throat this way too big dick. I even video taped this. It was great watching me suck cock while I smoked and swallowed my sperm.
This dick was far too big for my butt. I tried a few times and got it all the way in, but it was just too large. So I bought a smaller life like one. This was also a viborator. I had many hot nights fucking my butt and cumming in my mouth. I was becoming a real cum slut.
It was never my intension to try to be "passable" but I had a desire to feel more feminine and my body was made for it. I'm 5"11' 150 lbs with long legs so I started to do some eye shadow and lipstick as well. I messed around with web cams a few times but never got a response that I wanted. So as you may have guessed I started putting ads on gay web sites. It was simple; Bi male, 40 yo likes to cross-dress; looking for a NSA man for some discreet fun, I'm an aggressive bottom that loves oral and wants to try anal.
I have had a few experiences with men but never satisfying me. They always had small dicks and didn't really get into the lingerie thing. After about a week or so of sorting through bs I finally found a guy that seemed real and interested in what I was looking for so we began our correspondence. He was around my age, lived near my work and had a nice body and what he described as a big cock. So the date was made! It was not my first time but I had a feeling that this would actually be what I so longed for. We exchanged photos and that was all I needed. He was very good looking, 175 lbs and 6 ft tall. Divorced and lived alone. I told him of all the things that I would like to do and he responded very positively. He was especially into the lingerie and even thought that smoking could be sexy. Score for me! I had a few days to get ready and I wasn't going to suppress anything with this guy. The day finally came. I was going to meet him at his place after work. That morning I prepared my "bag" and finished work early. I went to the Y and worked out as normal but showered in a "family" stall dressing in my white corset, seamed lace top stockings with Cuban heels and a thong. Over this I put on sweats and a loose fitting shirt. On the way there, I stopped at an old warehouse parking lot and finished my outfit in my car. I wanted to arrive fully dressed as we agreed. First a tight leather skirt and a chiffon top; got those at Good Will, then a little lipstick, eye shadow, mascara and the wig. I was now ready for the 5 minute drive to Mike's house.
I took a little bit of a detour and smoked a 120 and debated if I could really do this. But one look in the mirror told me,
"Yes, this is it. It's what you want and need. Don't back out now". So I continued my drive and pulled into his drive way. He had a very nice townhouse with a private drive in the "upscale" section of downtown. OK, I thought, go for it. One last drag and quick sprits of perfume then I put on my white 6 inch "screams" with metal spikes, opera gloves and grabbed my bag and knocked on his door. Yes I was very nervous but extremely turned at as well. He answered the door and said "Jill"? I took the opportunity for some levity and said'
"No, is this the women's PTA meeting"? A laugh from him broke the tension and I answered,
"Hi Mike. I'm Jill" his response was, "holy shit, you're beautiful" the door opened more and I walked in.
His place was very clean and nice as I sat down on the sofa. He asked me if I wanted a drink and said sure.
"Beer or wine"? "Beer thanks". He returned with a couple of brews and we started a conversation. Small talk at first then a brief history of our sexual past. As the beer began to work on our nerves we started to move towards each other. It was very slow and extremely sexy. We looked into each other's eyes and our mouths met. I slowly began to put my tongue in his mouth as he did to me. We were actually making out. I love to kiss and find it one of the most erotic parts of sex and he was no slouch at it, very sensual and controlled. I loved it.
We could have kissed for hours but both knew we wanted more. I got up and asked where the bathroom was. I grabbed my bag and excused myself walking slowly to the lavatory. Once there, I quickly took off the skirt and top leaving me in my sexy lingerie. I grabbed a cig, light up and proceeded back into the living room, my heels clicking on the hard wood floor. His pants were still on as he watched me with a very seductive look. I put on my best show for him. Modeling my lingerie and demonstrating my skills at seductive smoking. He was very receptive to this as I looked at him while doing French and "snap" inhales. Yes, I love the smoking part. Always have.
"Wow, you're so fucking hot" was his response! I said,
"I know, so are you Mike". With that he stood up and we began to kiss again. I took off the heels not wanting to be taller then him. This time, our kiss was much more deliberate and intense. As I sucked his tongue, I started to undo his belt and zipper with my free hand. His pants fell to the floor leaving him standing in his tented jockeys.
We stopped our kiss and I stepped back and looked him in the eyes and said,
"Can I suck your cock"? It wasn't really a question as I pulled down his underwear exposing the most beautiful dick I have ever seen. He was ½ hard and already at least 7 inches long, cut and cleanly shaved. At last I thought a real dick and a real man! I began by kissing him on the neck and slowly moved down his chest, sucking his nipples, and licking his stomach. With my right hand I began to stroke his cock while holding my 120 in my left.
There it was a penis, long, thick and getting hard. I was so ready for this. All those years of wanting it and now I was going to do it! Dropping to my knees slowly beginning to lick the crown and ring of his masterpiece, tasting the wonderful sensations of cock. Oh how I love oral sex. He began to moan as I kissed and licked his shinny purple head. I was about to suck the cock of my dreams and. I looked up at him and said,
"I want your cock in my mouth, I'm going to deep throat you and swallow your cum". I licked my lips, opened my mouth and wrapped them around his cock. Slowly I moved down his shaft bringing him towards my cock loving throat, taking my time sliding down this incredible dick. With every centimeter I felt more and more lust for giving head. It was that most erotic, sensual feeling I have ever encountered. It was beyond my wildest expectations. His dick was in my mouth and I was giving a blow job to a man while dressed a women. My ultimate fantasy was now real.
I moved my mouth down his cock until the head was touching the base of my throat. My desire to deep throat him was going to happen. I relaxed my muscles and brought him into my in. He gently pushed the back of my head and soon he was there, telling me how great it felt saying,
"Jill, suck my cock baby. Take it all. Oh yes your a great little slut. Suck it honey, suck it Jill" And I did. This was the most incredible experience I have ever had, deep throating an 8 inch penis without the slightest difficulty. It was beyond words. He was never rough at all. The whole time being sensual and very gentle with me. Soon, he told me that he was going to cum. Now I wanted to make the most of this so I backed off and relaxed while I strocked his dick and grabbed another 120. I said,
"Mike, I want you to cum in my mouth while I jack you off". I took a long drag from my 120 and brought him back into my mouth while I stroked his shaft. I could feel him starting to cum as his balls got hard as he began to moan. Yes, I was going to swallow his cum soon and I could not believe it. My mouth was covering about 2 inches of his shaft while I jerked the rest of him with my hand. He began to pulse and thrust in me saying,
"I'm Cumming Jill. Take it. Swallow my cum baby. I love it. I love you". Then he let go. His first shoot went into my mouth followed by three more huge spurts as I pulled his dick from my mouth and jerked his shaft onto my face sending another three or four shoots on my lips and face. I was covered in his cum and had a mouth full as well. He began to subside and shot the remainder of his cum on my chin. I looked up at him showing the sperm in my mouth and swallowed. His cum tasted so much different than mine, salty, sweet, warm and wonderful.
He sat down on the sofa relaxing, reveling in post orgasmic bliss. I crawled between his legs and looked up at him. My face was glistening with his jism. He quietly said,
"That was the best bow job I have ever had. You're so hot Jill". I responded,
"It was all my pleasure Mike". I slid up next to him and offered my mouth and kissed him. He began to lick my face and suck his cum from my mouth. We shared his orgasm while I finished my 120. We chatted for a few minutes while he refracted. I was no where near ready to stop. He had mentioned to me that it would be hot to video tape our encounter and I asked him if he would like to continue someplace more comfortable.
"Yes, I'd like to" and he excused himself and went upstairs, leaving me alone wondering what was to come next. Five minutes later he called me to his bedroom. I walked up and found a really nice full size bed with satin sheets and pillows. He had set up a video camera with a monitor on the dresser. This was hot and I was ready for what I knew was coming next. I jumped on the bed with him and we started making out. He switched on the video and our images appeared on the screen. How hot is that, me dressed in lingerie kissing this stud? I broke our kiss and said,
"Mike, fuck my ass. Put your cock in me baby. I want it so bad." He started by licking my face and moving down my body. I rolled over as he kissed and caressed my butt.
I had never had anal sex before, but all the dildos I had used in the past assured me that I was more than ready for it. After a few minutes of kissing my rosebud, he got up and went to the dresser grabbing a tube of Astor glide. He liberally applied the gel to his cock and then spread some onto my pretty little butt hole. He placed a pillow under my stomach and I exposed my cherry to him. Oh man, I was so hot for this. He began by rubbing his cock head up and down my rear. Then he placed his head on my boy pussy. He was very gentle and slowly pushed his dick inside me. All the time he was telling me how hot I was and that my ass was perfect. It was so sensual, erotic and romantically slow. Just what I wanted. I could feel every contour, every vein and muscle of his cock as he pushed gently inside me. Soon, he was at my prostate and I was beyond control. I have spoken with guys before about anal sex and how great it felt. This was well beyond any fantasy for me. I could not believe anything could feel this good. He was awesome. The whole time he pushed into me. Never withdrawing until he had all of his 8 inches inside my pussy. There was never any pain at all. It was so natural and easy for me. I then felt his balls touching my ring and then asked him to fuck me. He pulled out and then pushed back inside, slowly at first but then increasing the tempo. It was marvelous.
Soon I was becoming a little slut and was begging him to screw me harder. I switched positions at that point and got on my knees and he quickly began to fuck my ass doggy style. I looked over at the T.V. and saw the most incredible sight I have ever witnessed. This man was fucking me. What I needed next was another 120. It's all part of Jill I guess. I lit up and watched his cock go in and out of my ass while I smoked and cried for more. "Fuck me Mike, screw my tight ass. Give it to me baby. I love it". And he did. We again changed positions and now I was on top. Our pace was getting really fast and I started to feel very slutty. I wanted to taste my ass and his cock. I told him this and he pulled out of me as I dropped down to his shinny dick and sucked his shaft. I could taste myself on him and I found it to be insanely hot. My ass, his dick it's beyond words. I was such a slut. We resumed our cowgirl position and he started to fuck me like a wild man. In and out, fast then slow. It was so sensual but hard core at the same time. There was no way he could last much longer as he began to thrust deeper inside me. That's when I lost it. I started to cum with his cock deep inside me. A grabbed my shaft pointing it towards his chest and let go. My sperm shoot all over his upper body and face.
"I'm going to cum Jill" was his response. I was so fucking hot at this point that I could barely control my actions. I wanted him to cum in my ass but also needed to swallow his sperm again. So I pulled off of him and went down on the cock that was in my girl pussy. He began to scream and then started to cum in my mouth. This time I kept his shaft inside me as he shot his beautiful sperm down my throat. I swallowed most of it then brought my face to his and we again shared his essence.
Totally spent, we hugged and kissed and then fell asleep in each others arms. Later that night, we woke up and began to simply kiss and hold each other close. When morning came, we showered and sucked and fucked again. I can't tell you how great this experience was for me. We became lovers at that point and continue to explore each other in ways I did not know could happen.
It's all true and I would like to tell you more. Hope you liked reading this as much as I loved doing it. Would you like to hear more? Let me know. Jill.