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I have been cross-dressing since I was a young teenager trying on my mother’s clothing whenever I had the house to myself. I was now out on my own and between relationships. I thought I was a heterosexual male, having only had sex with females. I was not attracted to males at all. All my relationships were with females, several long-term girlfriends included.
Since living on my own and moving to a new small town for a job I spent more time at home cross-dressing and building my wardrobe. I spent many nights cross-dressed and masturbating at home. More and more I began to fantasize about dating men while dressed. I was an avid reader of penthouse “Variations” and the cross-dressing stories were my favorites along with the domination ones. I was not gay or did not think I was but I was curious for sure and decided to act on those feelings.
It was many years ago before the Internet. I met a guy through one of those TV/CD Chronicle magazines from the adult book store. People would take out ads looking to meet for kinky sex. You would send two dollars per letter a photo (optional) and self-addressed stamped envelope with ad number written on the envelope. The magazine would forward it on to the contact and they would write or call you if you interested them.
I sent responses to several advertisements and received several return letters. I sent no pictures of me, but got some pictures back. Biker boy (my nickname for him) was not one who sent pictures. He did include his phone number and he wrote a nice, yet rather messy return letter to me. It seemed heart felt and sincere. His letter stated he was looking to meet and play with a TV/CD preferably one that was dominant. I was fascinated by the BDSM lifestyle yet my only exposure, was the many porno magazines I had read on the subject and a couple role-play scenarios with an ex-girlfriend where she spanked me and used her dildo on me. I gave Biker boy a call and it went something like this;
Hello
“Whom am I speaking to?”
This is Mike, who’s this?
“This is Mistress Gloria you sent me a letter”
Oh Hi,
“That’s no way to speak to a Mistress is it?”
No Mistress I’m sorry (boy did his voice change from Hello)
“You must always address me as Mistress Gloria”,
Yes Mistress Gloria,
“So you want me to be your Mistress”
Yes Mistress Gloria.
“Are you alone?”
Yes Mistress.
“Then take off your clothes now, you can put down the phone but hurry”
I’m back Mistress,
“Good now get your cock hard and answer some questions”
I can’t remember the rest of the call in detail, but he told me his cock was an average six plus inches, fairly thick with big balls. He was about 5’10” stocky, muscular with a small beer gut. Just an average looking guy and he lived alone in Jacksonville in an apartment. He said he had never been with a CD or Mistress and wanted to try it. He would do what ever I wanted; I could come to his house or meet in a motel. We could meet somewhere neutral like a club or restaurant if that was what I wanted. Meeting on weekends would be best and that he work half day Saturday mornings.
I told him nothing but if I decide to visit, he would not be disappointed. I told him to strip naked and jack off for me right now. He should talk dirty to me while he was doing it and he should eat his cum when he was done. He did, at least I think he did, or he was a good actor. I could hear him slapping his meat and his breathing was erratic. I told him I would think it over look at my schedule and get back to him. When I hung up, I finish myself off I was rubbing my cock over the top of my panties the whole time.
I was very turned on by the whole scene, the letters, the phone call, him calling me Mistress, jacking off for me. I had not had sex with anyone for six plus months since I had moved. He lived about two hours away by interstate. I could not stop thinking about meeting him. I was torn I wanted to meet him yet I was scared. I wanted to cross-dress with someone else and come out of the closet even if it was just for one person. I had mixed feelings and yet I was extremely horny and excited. After three days of complete torment, I decided to call him.
I called him back to arrange for our play date. I told him we would meet on a Saturday less than two weeks away. I gave him a list if conditions he must meet before or date. istanbul escort We would meet at his pace and I wanted it to be clean and neat. He was to ail mail me a map and directions to his apartment from the near exit off the interstate. I wanted a gift from him and I gave him my sizes I wanted some article of woman’s clothing. He was to have several bottles of chilled Chablis waiting for me.
He was to be clean and freshly showered. He was to be completely nude and on his knees when he answered the door to me. I wanted all the blinds and curtains closed to insure our privacy. The room softly lit with scented candles burning. I also told him if he did not do every thing I ask I would stop and leave immediately ending or date. He had to trust I would not hurt him because I trusted him the same. He agreed to every thing no questions asked. I told him not to touch himself at all before we met.
I drove down the night before and found his place then drove to the nearest motel for the night. I bathed, shaved, used a depilatory and gave myself an enema. I was smooth as silk and I used some nice lotion on my freshly shaved body. I put on a bra and panty set plus pantyhose. Then put on a tee shirt and jog suit over every thing. Then I went out to have some drinks. I was nervous as hell and needed to relax. That night I lay in the bed and played with my self but denied orgasm. I also played out in my mind many different scenarios for our meet tomorrow.
I showed up at his place the next day around two in the afternoon. I had on my black Shorty girdle, black long line bra, stockings, 3″ stacked-heeled boots, black jog suit and women’s trench coat, light make up. When I got in he had done every thing I wanted, he was naked on his knees, his place was clean, and he got me the wine and a nightgown for a gift. I took off my coat and jog suit had him get me a glass of wine. We sat in the living room of his small one bedroom apartment and talked. This is when I learned he was biker boy. He had many tattoos; there were motorcycle magazines around and a helmet on one end table. There was also Harley parked out front. He was bigger than I was and stocky, older, and burly, could have kick my ass if he wanted to. He was such a pussycat with me, spoke softly did not cuss, did every thing I ask, even if he was a bit rough around the edges. He treated me with respect and like a real Lady.
He like me was very nervous; he sat on the floor at my feet like an Indian I had to tell him to put his hand at his side so I could see his cock. I drank my wine and smoked a cigarette while we talked. I mostly talked he just answered when I ask him a question. After finishing my glass of wine, I had him take my bag and set it by the bathroom door.
The bathroom was in the bedroom. I had him lay on the bed, I tied his hands, and feet then blindfolded him with a silk scarf I had. I could see him from the bathroom he just laid there silent. I had tied up his cock and balls with a thin leather purse strap. I took this time to finish getting ready.
I would watch him from the bathroom, then go in, and tease him while heaving up my make up. fixing my hair and putting on my dress, Mike’s balls were huge, they didn’t fit in my hand, fuck the were awesome, I would kiss his cock and balls, then work on make up, twist his nipples, kiss his nipples and lips. Then work more on my makeup, then more teasing. I carried on like this for 40 minutes or so. I finished with my make up and dressing. I took off the blindfold and he went nuts, I had on a low cut red dress with big black buttons down the front. I had tucked the cups of the bra into the corset like bodice of my long line bra. I had been wearing suction cups on my nipples and they were huge, puffy, and dark. You could see them with my low cut dress. I knelt on the bed and let him suck and lick them while I played with his cock and balls, he got hard as a rock and his balls even swelled larger. He was a hairy but his cock, balls and ass were shaved smooth. So licking his cock and balls was great.
I didn’t stroke him but did just enough to keep him hard. I was getting hard from playing with him; I was in love with those giant balls. We went into the living room. He got me another glass of wine. I had him sit at my feet and licked my boots. He had to lick the buttons on my dress before I would unbutton it. I played with cock and balls with my boots, just escort bayan enough to keep him hard. He licked me all the way to my cock, legs, knees, thighs, even my panty covered rock hard cock. My cock was bigger than his was, but both my balls were smaller than one of his. I was quite taken with his huge bull balls they were impressive.
Then I spanked his ass OTK, first with my hand, then a wooden hairbrush, Hard too it made his ass dark red. He was a big strong tough guy but I was really laying in to his ass. The hairbrush packed quite a punch and it was taking a toll on him. I would lightly scrape his ass between spanking attacks with my fake red fingernails. We had not talked about limits or a safe word. I would ask him how he was doing during the short breaks I took while spanking him. Then I would tell him I was going to continue and I
would say all right, he would always answer, yes Mistress.
I was enjoying the power I had over this big strong man. I am petite short, 5’4″ and 135-pound male with blue eyes and long natural blond hair. Biker boy had to have weighed 75 pounds more than me and was taller by at least half a foot. I am scrappy but I think if he wanted to, he could easily over power me. I continued my assault on is his ass until he started to react with whimpers and grunts of pain. He also began to squirm and try to wiggle away from my blows. I had been spanking him for at least thirty minutes his ass was now red slightly blistered and was showing signs of bruising. He never complained never once ask me to stop, he took his spanking almost silently until the very end. When I stopped spanking I rubbed his ask for sometime while he was still on my lap. I had captured his cock and balls between my stocking covered thighs and squeezed them and released them, I repeated this until his cock began to stiffen.
We had now been at this scene for close to two hours. All my apprehension and nerves were gone. I was very comfortable and at easy not to mention very turned on. My cock had been in a semi state of hardness from the time I walked into the apartment and had been leaking precum the entire time. It was now time to get on with the sex portion of our play date.
Then I had him kneel before me on the floor and lick my boots all the way up my thighs to my panties. I had him lick my cock and balls when they were in my panties until they were soaked. Then I stripped off my panties and moved to the edge of the couch. I told him to suck my cock, lick, and suck my balls. He did that with enthusiasm and I was hard in no time at all. Sometimes I would grab his head and fuck his face. I almost came several ties but would push his head away at the last second before I came. I would settle down then have him start again. At one point, I even pulled my legs up and had him lick my asshole. At my direction, he was driving me crazy with lust. I had never had this complete and total control over anyone before and I was going to make it last. I had never been with a man before but that thought was not on my mid I was just having sex hot nasty wonderful sex gender was not a concern now.
Finally, after two stoppages I could not hold out any longer. When he had me hard and ready to cum for the third time, I grabbed his head shove my pulsing cock as far as it would go down his throat and released spurt after spurt of my pent up sperm. I held his head with my hands and thighs until I regained my breathing and my cock shrunk. I know I must have blacked out even if it was just for a second or two. It took me about 5 minutes before I wanted to move. Biker boy just lay still tonguing my soft cock until I pushed him away.
I was wiped out but I was not done. I had Biker boy get me another glass of wine and I smoked another cigarette. I made him first get his vibrator then had him lie on the floor and get him self hard. I played with his balls with my boots, flipping his balls with the toes and softly mashing them with the soles and between my feet. He was hard in no time at all. I found his little display very arousing and began to play with my self also getting hard once again. I stopped him again when I saw him enjoying himself and getting close to cumming.
I then tied his balls with the leather purse strap. I wrapped around the base of his balls twice before tying it off. I then had him get on his knees in front of me resting his head in his hands on the floor. His red Pendik escort ass was just standing up in the air right in front of me. I then worked his vibrator into his ass, slowly inch by inch using just a little lube. He was now starting to moan and grunt as I work the vibe deeper and faster. The vibrator was about seven inches long with a rounded point and tapered to about the diameter of a golf ball about half way down the shaft to the base. I continued working it into his rear until I could shove the whole seven inches all the way in right to the base.
When I started to pick up speed and force, he became much more vocal grunting moaning, ahhing and ouoohing. I knew it must have been uncomfortable but he never complained. I continued to punish his ass and then started to play with his big swollen balls. Stroking and squeezing the every so often stroking his semi hard cock also. His balls were tight and in his tied scrotum and the two of them fit in my small hand like a softball. They were turning purple and I think swelling even more it was an awesome sight and I found it highly erotic. He was now lost in his own world moaning, sweating, thrusting back on the vibrator plunging deep into his colon, sucking deep breaths when I would squeeze his engorged scrotum. My cock was hard from the scene before me I was not touching it. Both of my hands were busy with stimulating him.
I fucked his ass for about 20-30 minutes with his ribbed vibrator with no mercy. When I turned the vibrator on he began to get frantic trying to squirm away but I admonished him and told him to be still. Now with both my hands on the vibrator I started to fuck him violently fast, deep and hard. He told me later that this violent fucking was very intense. That it hurt at first then felt great, and he just took it. He never thought for a minute to ask me to stop. I could only keep that pace for a few minutes before I had to stop. I shoved the vibrator all the way in to his ass and made him roll over onto his back. I didn’t really know what I was doing, I do know no girl ever let me ass fuck them that hard.
I then had him lie on the floor and masturbate for me, while I stroked my cock. I couldn’t take it for long I was highly aroused. I dropped to my knees and straddled his head feeding him my ass again. I stroked my cock while he licked me and masturbated himself. When he started to get off, I attacked him with my mouth, my first taste cock. I just leaned forward and deep throated him, he was not long or thick he was just average cock wise. I spent a couple minutes slobbering and sucking his cock and balls before he finished in my mouth. I sucked spurt after spurt from his humongous balls, I licked up what leaked out and even snowballed some on to his balls just so I could lick it off.
Then, with him on his knees, I had him suck me off while I face fuck him for the second time. I made him gag a few times. Finally, I collapsed on the couch for him to finish me, I held his head and with my cock in the back of his mouth gave him a good load. I even held him there after I was done and made him suck my soft cock. Then I actually made out with him on the couch some while I recovered. We talked some about how intense and exciting the whole scene was. Both times I came were very powerful, much of what we did was spontaneous neither of us hand done anything like that before.
Then CD remorse or guilt hit me. I suddenly needed to get out of there. I went to the bathroom and stripped off my make up, I took off my dress and stuffed everything into my bag and left. I left my panties, bra, girdle, hose and boots and pulled on my jog suit then left. He pleaded with me to stay longer and even spend the night but I never considered it. CD remorse is kind of guilt after you cum. The excitement is gone there is a big let down and embarrassment. You just want to get out of your things. I don’t get it much anymore, but it was strong that day.
During the two-hour plus drive home I was absolutely giddy and proud of myself. I had my first bi experience and it was thrilling. I cross-dressed for a stranger for the first time ever. I role played as a Mistress, gave my first spanking and experienced my power exchange ever. Suck cock and swallowed my first load. Yeah I did it and God it was hot. It wasn’t gross and I was amazed at how his cock felt. His gigantic balls were such a turn on. I played with my cock most of the drive home. I even pulled over in a rest area parked way in the back in the corner and jacked off for the third time that afternoon.
I never contacted Biker boy again but he opened a new chapter in my life that day and for that, I hold a special memory of him.
Ben Esra telefonda seni bosaltmami ister misin?
Telefon Numaram: 00237 8000 92 32