All people portrayed in this story are over the age of eighteen. Please feel free to e-mail me as I am glad to respond. Always open for suggestions and willing to chat about stories. Feel free to use anything from the story as I could care less about copy writing and feel that nifty.org is a wonderful site for letting us express ourselves for free. I only hope I am getting better at this writing thing as we all may have the same fantasies I am only glad I could share mine.
I woke early in the morning still dressed in my bra, no panties, garter belt and stockings. I was so beat from the night before I did not feel like changing into my nighty for bed. The guy I met at the hotel bar had only left about four hours ago.
Last night I had only gone to the hotel bar for a drink or two before heading back to my room to spend another night alone. I went to the bar dressed as a man but underneath my male attire I was fully body shaven and toe nails painted bright red. I also wore my red satin matching bra, panties, and garter set with black shear stockings. As I love to cross dress but never had the confidence to go out in public fully dressed this is the next best thing. I was the only person in the bar so far that night. While I sat perched on the bar stool watched some television I had not noticed a man sitting at a table behind me until the bartender went over to get his drink order. After the bartender dropped off his drink order she went to the back room for something that's when the man came up a sat next to me at the bar.
He introduced him self to me and he and I exchanged hellos. That's when he hit me with a big question. He told me not to take offence but wanted to now if I was wearing a bra and pantyhose under my clothes. I turned red and my hands began to sweat. I did not know what to say. He repeated that he was not any way offended by men wearing women's clothes only interested. I inquired from him how he knew, he said from his table he could see the strap of the bra through my shirt and could also see the nylons when my pants rose above my shoes. In the mean time the bartender came back and he wanted to know if I would join him at his table. I agreed and we picked up our drinks and headed back to his table.
At his table I confessed to him how I loved wearing women's clothes and from the time I was about eleven years old how I would borrow my sisters and mothers stuff to dress up in. He bought us more drinks and this loosened me up to tell him more about my kinks. I also confessed to him how I wanted to try a real cock but never did because I did not find men attractive and how turned on I had gotten when I had been paddled at school. This lead to him telling me he was married and was bi-sexual, he and his wife love to swing and she was in another of the hotel rooms right now with another girl they had meet on- line. He told me how they love to role play mostly her in the Dom role and he as her slave. Then he asked me if I would like to take this back to my room as he wanted to see me fully dressed as he had never been with a man dressed as a woman before.
He followed me back to my room with a couple more drinks in our hands. He went and sat in the chair as I sat on the end of the bed and I asked him if he wanted to see me fully dressed or just what I had on underneath. He said he would love to see me in my full attire. I got up off the bed went to my bag and grabbed some shoes and a dress and went to the bathroom. I took off my male clothes and slipped my black dress over my head. I check my self in the full length mirror and admired the dress that fell four inches above the knee, with a choker type collar with two pearl buttons, long sleeves, and slits on either side that showed just a little stocking. I slipped on the pair of black four inch high pumps, with open toe, and sling back straps on my feet and step back out into the room.
As I walk into the room I could see his eyes look me up and down while he straightened up in the chair. I asked him if he like my outfit and he nodded yes, then I asked him if he did not mind that I hadn't either make up or a wig on, he just nodded no. I went and sat back down on the edge of the bed and crossed my legs at the knee were I nervously pumped one foot freely in the air. The chair was close enough to the bed where he leaned out and put a hand on my knee. He wanted to know if I minded, with that I put my hand on his and patted it as to say it was o.k... He then took his hand and placed it on my calf and felt my leg from behind the knee to my heel. I slipped off the other shoe and placed my stocking foot in his lap. With my toe I rubbed his crotch and could feel how hard he was. He than grab the leg he was rubbing and removed the other shoe he began to rub my foot in which I then leaned my head back and closed my eyes.
Then he broken in and asked me if I wanted to suck that real cock tonight. I lifted my head back up and looked him in the eyes and told him yes. I removed my feet from his hands and lap and fell to the floor on my knees just in front off him. This was something I always wanted to do when I dressed up as women but was always afraid too. He was reaching to undo his belt and pants in which I leaned in and undid them for him. I put my hands on his waist band of his pants and underwear as he lifted from the chair. In one quick move I had pulled them both down to his knees. He set back down and lifted his legs so I could remove his shoes and his pants the rest of the way. Placing both hands on his thighs I leaned my head in and put the tip of his cock to my lips and kissed the head. I then moved to the base off his cock and licked the underside off his cock from his balls to the tip, which made his cock jerk. I then wrap a hand around his stiff member and flicked my tongue rapidly on the sensitive underside just below the head, he moaned. While looking up into his eyes I engulfed as much cock as I could then began slowly at first to suck him off like I would have liked to be sucked myself.
After blowing him for a few minutes he let go of some pre-cum I slipped my mouth off so I could taste it better. When I was going back down on him he asked if he could fuck me, I thought he was just talking dirty, he asked again as he put his hands to my head and lightly lifted me off his cock. I looked at him and decided to say yes. He helped me up and took me by the hand and led me to the bathroom. He asked me to hand him some lotion and to place both hands on the sink and bend over. He lifted my dress up over my ass then pulled my panties down to my knees. In the mirror I could see him squeeze some lotion on his finger. With me bent over he place a hand on my shoulder and placed the lubed finger to my rose bud, he slowly circled his finger around my opening to grease it up. Then he put more lotion onto his finger and told me to relax, with that I felt his finger touch me again but this time he expertly inserted it slowly. I felt him slowly fuck my ass with his one finger, I began to relax, he than inserted a second finger and stuck it in deeper and deeper then held it there until he could move them both in and out freely.
When he removed both fingers, I had moaned, I had never had anyone else fuck my ass other than myself using a dildo. He grabbed the lotion and smacked my ass as he had me follow back to the bed, I removed my panties the rest of the way and tossed them aside. I then without being told got up on the bed and knelt on the very edge with my feet dangling over. I could feel him step up in between my legs then he place one hand on the small of my back. I turned to see him cock in hand aim it straight for my hole. He placed the tip right up against my opening and ever so slightly enter me. His cock head slid in just passed my muscle then he stopped and waited till it relaxed till he slid in further. He did this until I was loosen enough for him to start fucking me. When I had loosened enough he fucked me slowly, almost pulling out then ramming it back in, then repeated this several more times. When I started pushing back he began to fuck me faster, grabbing my hips with both hands he fucked me harder and deeper. I was in heaven. As he thrust deeply and harder he pulled out just as quick, with his hands he guided me to turn around and lay on my back. Placing both hands on my ankles he pulled them up and forward were both knees almost touch my chest. In this position I could see his face as well as my nylon clad feet and legs which was a real turn on. This time without any effort he began fucking me again. I could see on his face he was getting close to cumming with that he pulled out and with one quick motion dropped my legs and they hit the floor. He placed a hand around the back of my head and lifted me, I took the hint and drop on my knees on the floor in front of him. His other hand was jerking his own cock; I then opened my mouth and waited. He shot his first load straight across my face his next shot had better aim and went right into my waiting mouth. He shot load after load into my mouth, I showed him his cum on my tongue before I swallowed.
He collapsed on the bed as his phone rang, it was his wife she was done with new found friend and told him to meet her in the lobby. He said sorry he had to go and did not have time to return the favor. I was not upset at all. He asked how long I was in town for and I told him through the weekend till the middle of next week, in which he asked me for my number, he was going to talk to his wife and see if he could return the favor later. With that he was dressed and out the door. I myself removed my dress jerked off and went to sleep.
As I said before just woke up and lay in bed for awhile thinking about last night, god I was really getting horny. I was going to be around through the weekend wondering what I was going to do to top last night off, so I decided that I might as well going shopping. It was not just shopping but shopping for some sexy shoes and lingerie. I got out of bed and went to take a bath so I could shave my leg and such. After I was done and deciding what I should wear my cell phone rang. It was a number I did not know I did not give it a thought and answered the phone.
When I answered my cell phone it was a man on the other side. He said his hello and wanted to know if I new who it was. I told him sorry I did not and that is when he said do you remember last night. We never did exchange names last night but I do remember giving him my number. We discussed the night before and he wanted to return the favor. I told yes and wanted to know if he wanted to meet me back at the hotel. As it turns out he told his wife about me and what we did and she wanted me to come to their house for a little party. The only thing was she wanted to know if I had any outfits like a schoolgirl or cheerleader I could come dressed as for our party. I did not have a cheerleader outfit but did own a schoolgirl outfit; I had purchased it on line from a store that caters to tranies. It was decided I would be at their place about three o'clock.
I was floating on air again thinking I would spend another boring weekend locked up in my hotel room but this time I was going to have the time off my life. From one of my suit cases, one for female attire other for male, I started getting out my schoolgirl uniform. Now I could not leave the hotel dressed as that so I just put on a pair of white cotton bikini panties, white lacy bra, and some suntan colored pantyhose. I packed the outfit up with some high heel shoes and would change when I got there. I pick out a very tight fitting genes and loose sweat shirt for my trip. When I got to the car I exchanged my male shoes for the high heels, as it made me fill like I was out in public without getting any looks since it would be hidden in the car.
I had arrived at their house just after three, I was nervous about getting out to got to the door since I was not sure if I did make it to the right house. Then the front door open and he was there waving me in. They live in larger home out in the country from what I could tell they had to be well off. I grab my bag from the back seat and proceeded up the driveway to the front door. I could tell again he like what he saw as he looked at me striding towards him. My heart was pounding and I could hear the clicking of my heels as I was getting nervous about getting together with him and now his wife. He let me in as told me how hot I looked in the heels. He said he was Jason and his wife was Holly and lead me up stairs to a bedroom.
While he showed me the bedroom his wife came in and introduced herself. She was about five foot four with short jet black hair. Her figure was gorgeous with firm breast showing through a tight white tee shirt and taut little ass in very tight genes. She said I should get changed in here and wait right there and don't leave as she would be right back. With that she grabs he husbands hand closes the door and they left. I did what she said and change into my schoolgirl outfit. Slipping out of my heels and genes I carefully removed my pantyhose and set them aside. Next I stayed in the panty and bra then slipped into some white thigh high stockings. I picked up the blue tartan skirt and step into it and straightened it around my hips. The white blouse was next along with a blue sweater that had matched with the skirt.
When I was finishing putting on the sweater Holly returned. She commented me on my outfit and wanted to know if I needed help with my make up. I said yes I could use the help as I was not very good at it yet. She then had me follow her to her bedroom I picked up my heels by the straps and danged then from my finger as I followed her. I was seated at her make table as she starting picking the right colors for me. She had me wait as she got another chair and sat beside me. I was to watch her in the mirror and mimicked her as she put on her make up. As we were doing this she would say I was starting to make a very cute girl and how fun it was to show me how to do it like she had a little sister. She than told me how sexy it was when Jason told her everything he and I did last night, even to the point of when I was eleven and how I love the school paddling. She also hoped that I did have the schoolgirl outfit and wanted to know if it was going to be alright with me if she could spank me. Of course I said yes and could not wait as it was another fantasy of mine that I was to be paddled dressed as a girl. We giggled and she went to he closet and got out a wig, it was black in color with pig tells all ready made up, she said it would be perfect for my outfit. I sat in the mirror and put the wig on and in the background I could see she was undressing. I asked if she wanted me to leave and go find Jason while she changed but she told me he was tied up right now.
As I was putting on the wig in the mirror I could see her put her clothes on. She had picked out a pair of see through lacy black crotchless panties. Then she put on a black matching six strap garter belt, I watched with lust in my eyes as she slid on the shear black stocking wishing I was her. Next came a long line bra with boning and cut low as to just cover her nipples. I told her I wish I could have what she had on. She then mentioned maybe her and I could go shopping together for some girly things later as she thought I would make a convincing girl and did not think anyone would notice. Holly completed the outfit with a very tight black a-line skirt, red satin blouse, and five inch patent leather pumps. She said for me to put my shoes on and to follow her as we were going to start our party with Jason.
As we were coming down the stairs to the basement family room I could see Jason was already there waiting, she did not lie he was tied up literally. We found him strapped to an incline bench. The bench was built in such a way that the person strapped to it was up about three feet from the ground kneeling on two out cropping slats with feet hanging over the edge and strapped in at the ankles and thighs. The person would be bent over the incline strapped in at the waist; arms are then strapped to the two other slats, and chin resting in a chin rest. Jason was this person strapped in to this thing but as she led me around behind him I could also see his ass was filled with large butt plug. As we walked around to the front his mouth was also filled with a ball gag. She then told me that Jason did mention to me the she was a bit of a Dom as she led me to a chair sitting in the middle of the room right in front of were Jason was tied up.
When we got to the chair she sat and I stood next to her. Holly then began to tell us both how very disappointed she was with both of us. She was upset that Jason went behind her back and hooked up with another girl without her knowing it. She was also upset with me saying how such a pretty young girl could let a man I just met fuck me. I was scolded how dangerous that could be and that I was going to be punished as a reminder never to let it happen again. Jason was also scolded on being caught with young girl could have landed him in jail. I understood this was this was going to be are parts in this little role playing game, her the dominating school teacher Jason the dirty husband caught with a schoolgirl and me the schoolgirl. Wow this was every wet dream coming true, I only hoped I was not dreaming as I would find out shortly.
While standing there Holly finished scolding us then she patted her lap and told me to lie across it. With that I lay across her lap with the tip of my shoes just touching the ground and hand resting on the other side. She had me look at the clock on the wall straight ahead of me. I was to tell her stop and only say stop once the minute hand had reach ten after the top of the hour and not before or she would start all over. It was almost the top hour when she began. Holly spanked me first over my skirted panty ass. When she stopped I felt her raise my skirt to my waist and started spanking again this time harder. Only after about a minute of abusing my panty ass she decided it was time to pull those panties down, she lowered them to my thighs and began to spank me again. Now with panties down and skirt raise only three minutes had passed, she was spanking me with more determination. Holly was spanking harder and faster alternating from cheek to cheek. I think she only paused to give her own hand a rest and when she did she would continue to remind me what a dirty cock sucking little slut I was.
I was beginning to really feel it now I had almost forgot about the clock. Then it hit ten after I said stop please stop and she did. Holly then had me get up off her lap and told me to go to the cabinet across the room. I hobbled over to the cabinet, panties still down around thighs, when I opened the cabinet I was taken aback by the amount of sex toys and spanking implements that were inside. There were dildos, strap-ons, bondage gear, a- long with straps, paddles, and canes. Holly told me to get her the large wooden paddle and bring it to her. The paddle was about two feet long and four inch wide, it looked just like the paddles that were used on me in school. If my erection was not all ready hard as a rock it got even harder. I reach in and grabbed it then brought it to the lovely Ms. Holly. I handed it to her then she took it with a smile and began tapping it against her thigh. She asked me if I knew what to do I nodded yes and turned from her to bend over and grab my ankles. She raised my fallen skirt and slightly touched the paddle to my already well warmed ass. I could feel her pull it away and swatted me; it was wonderful but painful swat. She wanted to know if that hurt but I told it was not all that painful. With that said she swatted me very hard five times in a row; I conceded that it was now painful. That had set how hard she was going to paddle me for the next forty swats I was to take like a good schoolgirl.
After receiving my paddling in front of Jason still tied to the bench I was told to remove my panties completely as I would not be needing them for the rest of the evening. I was told to stay right were I was and not to move an inch. I stood there with my skirt raised in the front like a tent and watch her go over to the cabinet. Holly hung the paddle back in its place my heart skipped a beat when she picked out a cane. She cut the cane through the air but it was not for me as I saw he walk toward poor Jason. She got in right behind Jason and slowly removed the butt plug she must have inserted into him earlier. After that she stood off to the side and behind him and placed the cane on his ass. She began telling him he would also receive forty strokes as I had taken with the paddle. I watched her strike her husband with a look in her eyes like she mean to do him harm. I could see Jason struggle against his bonds and tried to scream but the ball gag would not let him. I then made the mistake of moving, I had only put a hand to my mouth watching her tear into Jason. I was told that when she was done with her husband I was going to take his place.
When she finished striping Jason's ass she loosened his bonds and I could now see how he strained against the straps from the red marks that they had left. As he struggled to stand up he turned and I could see how bad she had beat him as from were I stood I could see very long red raised marks she had left on his poor ass. Holly then motioned for me to come over and take his place. She had Jason strap me into the bench. I was getting very excited but scared at the same time. After I was strapped in I could see she had already replaced then cane and return next to me with a very mean looking leather strap. The strap was black leather looked heavy in weight and painful. This time there was no warning when she took her first stroke against my ass; it was very hard and stung enough to make me yelp. I tried to move but could not being tied as I was. There was no counting there was no time limit all she did was tell me I had one order to obey and could not do that. I was giving a strapping till my ass was on fire. When it stopped I closed my eyes and caught my breath but I soon found out there was another place to administer punishment. I could feel my shoes being removed; Holly had replaced the strap with the cane brought to her by Jason. I then received five strokes to each bottom of my stocking clad feet.
After getting my feet caned I was left tied to the bench. I was now in a painful pleasure and wanted some relief but it was not going to happen soon. I looked around the room and found Holly had removed he skirt and was placing a black strap-on dildo around her waist. She had Jason kneel in front of her to give her fake cock a blow job. He was doing quite well as I wished it was me getting my dick sucked by his expert mouth. Holly then pushed him away, pick up some lube and got in behind me. I felt her lovely little finger grease me up for the fucking I was going to get from her. It was am amazing feeling of mixture of pleasure and pain she was giving me, first the beating she gave me now fucking me with her cock. As Holly was fucking me I did not notice Jason had stepped in front of me until I felt the head of his cock touch my lips. I willing opened my mouth and let him slid his cock in me. They both fucked each end of me till Holly came from fucking my ass and Jason lost his load in my mouth. They both untied me and lead me over to the couch. I could fell every stitch in the fabric from the spanking I had gotten. I did not care as soon as both of them took turns sucking me. Holly soon let Jason take control of my cock as she came up and started kissing me; this had pushed me over the edge as I shot a load of semen deep into Jason's mouth. I came and came but Jason never waivered as he was ever so careful of how sensitive my cock had become.
After that we fell to floor and rested hold each other. Holly was still quite aroused as I first watched Jason on top of her fucking. I could just stand by so I got in behind him and inserted my dick in his ass. This made him cum almost instantly inside of his wife. He fell off of her and I took his place with my tongue I ate out all of his seed as I could get while he got in under me to suck me off. Soon Holly came and came from me eating her out. I also came in Jason's mouth in which he saved until he kissed his wife and shared my seed with her.
After that weekend we all became good partners. I see them often when I am in their area. I now live more as women than a man and found a Master whom disciplines me often. He can not replace Holly as the disciplirian or Jason as a lover. When I do visit Holly and I do going shopping together for clothes and shoes but now I have the confidence to go dressed as women.
Natalie.