CD's and TV's are not really chicks they are guys and they have guy sex drives! Unlike many online Cyber Queens as I call them. Years ago I did do some cross dressing. Unlike those AOL and Yahoo frauds I really did dress up and unlike them despite digital cameras being new things and very expensive I did get some shots of me dolled up. I found lots of gay guys wanted to suck dick and be fucked by a dick. They didn't give a shit if I was wearing a gorilla costume. So I ignored them all! Anyone who had no pictures didn't get a second look from me either!
Finally I went out of town to Wisconsin on business to a hotel for a couple of nights. I knew this was my chance to really dress up go online and see if I could seduce someone into fucking me! Or at least find out if I had the nerve to go through with all or part my wicked fantasy! My first night I got completely dressed...body stocking covering me neck to toe...I didn't need it really because I had already shaved off all my body hair! I put on a sexy bob cut red wig, eye makeup and lipstick along with finger and toenail polish! Then I slipped into a form fitting dress and for a guy 40 years old I wasn't a bad chick! As it got late I hooked up the webcam and after spending almost two hours weeding out the total queers and fakes..I found a nice straight married guy who seemed to be very turned on that I was in the town right next to his.
I told him to have a couple beers to build up his courage and then he could enter the back entrance of the hotel and I would quickly sneak out of my room to let him in! Nervous I waited and did myself in the mirror a few more times. In about 30 minutes a car pulled up that fit his description...my heart pounded and I opened the back door and this 6'4" 200 pound man with sandy hair and green eyes met my eyes and looked me over. As I led him into my room he said "wow you look better than your pictures and webcam shots!".
I gave him a couple more beers and we started to laugh and have a real good time. I realized then one of us was going to have to make a move since we were both getting comfortable. I stroked his leg and moved my hand down his thigh as I offered to take off his boots.
This now got me on the floor on my knees in front of him. In perfect position I then unbuckled his pants and he raised his hips so I could pull them off. I opened his shirt up also to reveal a very nice smooth chest! He stretched out on the chair in front of me leaning back and saying out loud to no one in particular "oh man..I can't believe this is happening..." I pulled off his tight fitting boxer shaped undies to reveal a very nice shaved cock that was already more than half hard.
On my knees I spread my legs so I could lift up my dress and reach into the crotchless section of my bodystocking and play with myself while I started to lick his balls and stroke his wide 7 inch cock. I had only sucked a cock once before, years previously with a shemale who had a huge 8/9 inch fat cock and I know I didn't do a very good job on that baby! But now I was hot and ready to do better! More turned on than I had ever been seeing a cock. Especially this up close and personal I put a shaky feminine hand on his now very hard manhood.
I licked up the middle line of his balls...all the way to the underside of his dick and back down..I kept doing this and he closed his eyes as I stared back up at him...he sighed..."oh baby...that feels so good!" I sucked on the head of his cock and massaged it with my tongue..he then put his hand on the back of my wigged head and began gently pushing it down on his dick!
I took more and more of him into my mouth...and it filled me up pretty good. Like any novice dick sucker my teeth rubbed his dick several times..he was a real gentleman and said nothing. Finally I learned to suck it the way I like it sucked...all tongue and roof of mouth sliding back and forth like some hot wet pussy or even a tight wet asshole!
He was now gyrating his hips up and into my mouth and I controlled most of his thrusts by sucking harder on his dick the way you do with a really thick milkshake through a straw! He was hot enough now where he was making all kinds of noises and saying things like "oh..God..that is so good...you suck my dick better than my wife does...shit baby.." Then he said the magic word I was hoping he would say...he called me by my girl name I used when in drag. "Oh Jennifer...oh..baby..Jenn..that is so hot...oh shit you are going to make me come Jennifer".
Now I was stroking my own fat clit and I tried to time it so I would cum around the time he did. I rubbed and stroked his balls with my left hand while stroking my own with my right. He pushed his hips up into my face..and grabbed my head with both of his hands and let out a wicked grunt and moan that sent me into sex heaven..a dreamy place where time and the world we know does not exist! Careful not to bite on it or choke on it as his cock head slid down my throat..I held his cock tightly between my tongue and roof of my mouth maybe an inch or less from the back of my throat!
I could feel his cum releasing from the tight ball sack I had in my hands! They went from puffy little balloons to tight ping pong balls just as he climaxed..but it was his cock where I could feel the cum on its way the most...the shaft got rigid and wider as the cum rushed up to the head of his dick. I closed my eyes...took my hand off my own dick and reached up with that hand to grab one of his ass cheeks which was now off the chair as he thrust deeply into my mouth.
Then I felt his cum release out of his fattened cock head and into the vacuum that was my sucking mouth. It was smooth and hot and a little salty at first but also sweet on the after taste. One hard big squirt straight from his lovely cock and right down into my throat..again he had pushed my head all the way into his crotch and I was pushing his ass cheeks with both hands into my face also.
I know how good it feels to cum in someone's mouth without pulling out or back or having that person stop and finish you by hand..or gag..or choke and kill that precious moment! And I wasn't going to ruin it for him or me! A second then third squirt...each time I amazed myself as it slid down my throat like I had done it before when I knew full well I hadn't!
He wasn't lying when he said he hadn't fucked his wife in a week and hadn't beat off in 4 days! His squirting was timed evenly with his hip thrusts and I rolled with the wave..4, 5, 6 full squirts..and then about 4/5 after bursts..little shots that I also quickly swallowed. I felt like such a hot whore as I knew all the grunting and thrusting was coming to an end but I nursed his dick like a baby with a pacifier. But I give the boy credit here. He didn't yank it out my mouth and pull his pants up and run out of the door.
He laughed and sighed and told me it was the best blow job he had ever had! I smiled unable to speak as I was finishing swallowing that last teaspoon full he shot into my mouth. As chick like as I could I swallowed petitely and resisted the urge to rub my face in a guy manner and instead straightened my hair/wig and pulled my dress down not wanting him to see my dick and ruin a pretty good illusion I had created!
"That was very hot I said" softly and in a suddenly very femy voice concerned that he was pleased with me. Neither of us knowing anything about sex etiquette between two guys with one in drag pretending to be a woman. I put myself on the end of the bed in front of the chair where his completely nude body except for an open shirt was now sprawled. I looked in the mirror and primped a bit. He let out his first words of guilt for the night. "Lucky our wives can't see this huh?".
Like some 300 dollar a shot prostitute I fired back.."that is what hotels are for baby!". He laughed and then said the special words that made my night. "Is it OK if I stay awhile longer ya know?". Then just like the bubble headed slutty chick I had turned myself into I said "oh that would be great..stay as long as you like". We sat up on the bed and watched some straight television for a while. I am actually 6'1" 175..but next to his 6'4" 200 I looked girlfriend like. I leaned against his shoulder once I knew he was over that post orgasmic guilt we men feel for about five minutes after fucking anyone or anything or even jerking off. He pulled me into his chest..and then I suggested we put on some porn from Spectravision!
We chose the one alternative flick they offered. "Bi Now..Gay Later". It had all kinds of mixed action including our favorite scene one of the bi guys dressed up in bra and panties and thigh high stockings! He got fucked by the other guy while he fucked the real woman! Hot..hot and hot! My new "boyfriend" Steve I was now calling him and he kept calling me Jennifer which made my head swim! Was hard again in 15 minutes...and I gently stroked his cock the way you would pet a dog or cat.
We had already agreed online he would not have to satisfy me in any way shape or form. But I was starting to think he was having new thoughts about that. He kept asking me to pull up my skirt so he could see if my cock was aroused. He said it looked nice and hairless gently popping out of my black scalloped imprinted body stocking. Later when I got hard watching the steamy movie he began to stroke me while looking at the screen as if nothing out of the ordinary was happening. As I got hotter and hotter and panting he turned into me nuzzling my neck and kissing my cheek..( I was so glad I shaved my face twice earlier that night and had put on heavy makeup to cover any shadow) I was weak from almost coming while sucking him off earlier so in a couple minutes he was stroking me hard and whispering in my ear.
"You going to come for your man Jennifer?...You want to cum for Steve don't you?" To which all I could moan was ..."Yea baby...I wanna cum for my man" I could not believe myself I was lying in bed with a hot formerly straight guy pumping my girl dick for all it what was worth. I was going, going gone now..and he was loving it...he kept referring to my dick as a clit and pussy..."You know that hot clit wants to come..that pussy needs to cum doesn't it?". Cum I did...drenching the front of my bodystocking in the tummy area and up on to my raised sweater dress! Steve had clearly enjoyed this brand new experience as much as I did. Handing me some kleenex to wipe myself off, even helping out a bit.
His cock was now bulging and pointing upward and outward every which way he leaned. My breath was not completely slowed down when my new boyfriend Steve let me know he was not only a good lover but a demanding one also. "Jennifer baby..I know you just came..and you liked that didn't you?" To which I mumbled.."uh..huh..". I brought some rubbers with me..then with a bit of a wicked smile he added "the ribbed kind for extra sensation". I had never had anything but my fingers and a couple of not so hot tries with a vibrator up my tight butt! But I really was enjoying this whole kinky scene with Steve and actually wanted to satisfy him at this point. Even though I had not promised I would take him inside me that way.
So I took the rubber out of the package placed it in my mouth the way I'd seen whores do it..and some porn stars..I used my mouth as a condom fitter sliding it all the way down his shaft till the latex and his 7 inches had me to the gag point. I had already made sure not to eat much that whole day and I had already done my "girly douche/enema" before he got there. So I wasn't worried about the obvious possible non hygenic results of him probing my lower extremities so to speak!
He rolled me over on my back...lifted up my legs..or I lifted them in concert with him we were both of the same mind sets now. I was his chick..and he was my man and he wanted to fuck and it was my job to satisfy him completely. With my crotchless bodystocking just leaving my butt exposed he lubed up my asshole with his finger while holding my legs together with just one big hand while smiling at me and saying "I do this to my wife sometimes but she says it feels too big sometimes".
I knew that was my clue to keeping up the amazing sex you can't get at home theme going. So I took a quick deep breath, closed my eyes and felt him pushing and probing his dick into me! As the head finally slid in after about 2/3 minutes of trying. He began to slowly push into me with what I estimated to be a 7x5 inch cock!
He was enjoying the slow ride in and even pulled back a tad a few times as if to mark the territory he had just been at! I let out a not so feminine croak since the intensity of his cock now half way inside me had taken me over almost completely! "Oh God Steve..you are so big..Oh..Jesus..shit, slow and easy baby..oh...ahh.unhh..I hope I can take it all honey; I whispered in slutty tones! I want you inside me baby, oh please..make me a woman with your big dick! Make me your woman! Steve please"!
Then he pushed further slowly I felt that big cock get sucked in to me until I could feel his warm smooth balls against my ass cheeks. "Fuck Jennifer...oh God..you are my woman...now...you feel my cock inside you now...? Whose your daddy now? Mmmm? Whose your man Jennifer? You feel that?" Feel it?! I could think of nothing else! I wondered how he would move it in and out it was so snugly jammed inside me! But he smartly held it there while I stroked his lovely round ass cheeks as if to say "easy boy let me get used to all that manhood inside me!".
Now I was Silly Putty as he slid his arms behind my back and neck and pressed that smooth chest against me. Grabbbing my shoulders with his hands the way you would a chin up bar he pulled his hips back slowly at first; listening and watching me exhale and moan. Then all the way back. But then harder and harder each time. My ass felt like it was on fire..that velvet piston pushing up and into places I had never felt before. It was even hitting what I've since heard gay men and sex experts call the male G spot.
A place where a cock in the ass massages the prostate gland and causes an intense internal pleasure as if the sensitive skin from under your cock head were up deep in your ass! My dick even tried to get hard but I found you can only get so hard with a cock that deep inside you! It rubbed against his flat muscular lower abdomen and was like being jerked off by the friction there. A similar feeling to a woman getting clit and cunt stimulation at the same time I would imagine!
Now we were yelping things at each other and I know if someone was next door they had to think a young couple was on their honeymoon! For the first time all night Steve began kissing me. Shoving his hot tongue in my mouth and then kissing and biting my neck too. He inhaled the Givenche perfume I was wearing (and loved to smell on my wife) and he sighed and whispered hotly in my ear. "Oh you smell like a woman baby!" As my ass gripped his stiff manhood I quivered with these new found "mangasms" and found my little girl clit was close to exploding without being all the way hard either! Steve was deep in his own sex trance...pounding me now..so much so I knew my butt was going to be very sore afterwards but I did not care at that point!
Now convinced I had found my true kinky flip side partner (a straight guy who wanted to fuck another straight guy dressed in drag who wanted to seduce a straight guy!) I gave out a throaty whisper to my new hot love! "Oh baby you ready to come?" "Oh yea Jennifer I could come anytime now!".
I said "take off that rubber and fuck me like you do your wife!" He didn't pause one second he slid his cock out of me..pulled off the rubber and began to thrust away like a madman for 30 seconds and then as he came letting out a banshee like scream you would expect to hear from a first time paratrooper! "Oh shit Jennifer baby...oh my fucking God..you feel so good...fuck..I want you to be my woman all the time...I wanna fucking marry you and knock you up...you wanna have my babies don't you?" Squirming and writhing I was so far gone with him I'd agree to anything! "Oh yea Steve fuck yea..you can fuck me anytime..I'm your bitch..I'm your fucking cunt...oh shit please cum inside me..please..yea shoot those babies up into me...make me a woman!".
He made me a woman alright..I thought he had dumped a load in my mouth. My stomach was so empty and only beer and his cum inside it was making me a bit queasy in that department..LOL! I wrapped my legs around him as tight as I could while he came rivers into me. I cannot describe the warm wet feeling of having a cock driven into you that way except to say I get hard and have to jerk off to this day when I think of it. Thrusting and pumping...biting my neck...yelling "Jennifer..ah...shit..take my cum". He came twice as hard and twice as long as when he shot his load into my mouth. My ass and whole lower half felt the way feel when you lower your butt into a hot tub!
I pushed my girl dick against his hard lower stomach and actually came against him as my ass did pretty much the same it was so intense I must have passed out briefly because the next thing I know he was grabbing my face with his hands..going.."Jen you alright?" Coming out of the ether of that intense endorphin filled rush I smiled and kissed my hot man. Both of us no longer surprised that such sex had occurred without a woman in the room. Well there was a woman in the room but now it was just us two guys lying on each other panting, kissing, whispering, giggling!
Steve's wife was out of town that night and the kids were with her. So he stayed a few more hours till early morning when I suggested he might not want the light of day to ruin the illusion we both had worked so hard to create. He still E Mails me.and we did do it a couple more times after that. He was my first and only man I ever gave myself to sexually like that. He was always the man and I the woman. I never fucked him and he never sucked me off. He loves that and so do I as a matter of fact. He also admits the sex was the best ever! Me too is all I can say!
Now the best part of this story comes now. It is not some wild fantasy this actually happened to me 10 years ago at the Holiday Inn in Eau Claire, Wisconsin! It was during a brief but very sexy period when for some reason I just started dressing in women's clothes! It happened one day just like that. I was in my office on my computer and I had this wicked thought out of nowhere...I wonder what I'd look like as a chick?
At first I thought I'd play it on the Dominant side and there were many who wanted that but they all seemed as gay as May! Then there were the ones who wanted just to dress with you. Don't need a partner for that sorry. Then those who wanted to dress and then play! (fuck) Two guys in drag fucking..I never like the pictures but the feeling of two bodies in all that nylon, latex, lingerie is and was very appealing.
But finally I just acted on it and like producing a movie or a play the project had a beginning, middle and an end. I find the thought of it very hot and I wish I had videotaped our first session. I taped our third and last and that was still a very hot session! I made a copy for Steve that he keeps throwing out then writing me for another! But sadly I'm too old now to dress that way. Nothing sadder than an old drag queen! But every time I whack off to that video I am damn glad I let Jennifer out to play!
Since then despite what the gay culture crowd has said; my only venture back in has been a generous fellow who enjoys sucking me off with no reciprocation. I have used him 3 or 4 times over a 5 year period when my wife and I are at war! I maybe Bi but I won't be Gay Later!
The Former Jennifer now Jag...If you like I might tell you what our second and third times were like!