tagTranssexuals & CrossdressersThe High School Reunion

The High School Reunion

bydysfunctionaldreams©

It was the week of Thanksgiving and I had planned on going home to visit the folks as was customary. Recently with the advent of Facebook, many of my old high school classmates had been in touch with each other and had also set a meet during the holiday break. The place that was selected was an old dive bar attached to a restaurant. After checking in with the folks, I informed them that I was going to go meet up with some old classmates and for them not to wait up.

We got back to Ann's house and she brought out beers for Chris, Mark, and I. She poured herself a glass of wine and joined me on the couch. Chris and Mark seated themselves in the chairs that were on either side. We talked about things that had happened to each of us over the years while we drank our first, then second rounds of drinks. At one point, the conversation turned sexual and Ann eventually leaned across to me and started kissing me. I was pretty drunk, so I sat back on the couch and went with it. She stopped and took note of my casual nature and asked if I were more dominant or submissive. I had to admit to being more on the submissive side and her eyes perked up at the statement.

She stood up then and took my hand. She pulled me up off the couch and stood me in the middle of the room, with my back to Mark and Chris. Then she walked into her bedroom and came back shortly with a video camera which she handed to Mark. She told him she wanted a history of the future events of this night and showed him how to work it. Then she seductively came over to me and began to undress me. Before long, I was standing naked in her living room. Then she went back to the couch and ordered me to drop to my knees, crawl to her, then remove her panties with my teeth, which I did. Then she told me I had to lick her pussy until she had come all over my face.

After the pussy licking, she said I would be her girlfriend for the night. With that, she grabbed my hand and led me into the bathroom. Mark and Chris followed, Mark videotaping all the way. Ann led me to an old iron bathtub, and had me watch while she filled it. Then she ordered me inside and proceeded to bath me. She pulled one of my legs out and sprayed shaving cream on it, then shaved it bare. She did the same with the other, then my arms and face. She had me turn over on my hands and knees so that my ass was out of the water while she delicately shaved my ass until it was also as smooth as a baby's bottom. She made sure to have Mark get a close-up of my now clear asshole.

After the shaving, she had me stand and dry off. Then she walked me over to the counter where she bent me over. I heard her filling something with water, then felt a tube slide into my ass. I went to stand but she immediately pressed a hand to my upper back, holding me firm in place. She told me to relax and began to fill my insides with water. Once I was completely full, she had me go to the toilet and empty my bowels out. Once I had finished, she ordered me back into position for a second cleansing.

Once done with that, she led me into her bedroom. I stood naked while she went over to her dresser and pulled out some lingerie. Then she came over and made me step into a black lacey g-string. Then she attached a garter belt around my waist. She added a black lace bra, and then had me pull black stockings up my legs. She had to show me how to attach them. She added some breast enhancers that gave me two nice perky little breasts. Then she went to her closet and pulled out a short black skirt that went down just below the tops of my stockings and then a short sleeve thin black shirt with a low cut front. I could down it enough to see my enhancers, but realized that those standing in front of me could not. She finished the outfit off with a pair of two inch pump sandals.

She took a step back and admired her work, then brought me over to her vanity desk. There, she applied all kinds of makeup and found a black haired wig she had worn to be the short girl from the Scooby Doo cartoon. As she worked on me, I began to notice that I did look quite feminine. Once she concluded the makeup and wig, she added a necklace and a bracelet and then stood me up for a final survey. Both the boys whistled at me and then she agreed that I was about as girly as she could make me. The one exception to that conclusion was when she called me Karen from the doorway and signaled for me to head into the living room.

Ann went over to her stereo, put on some music and ordered me to dance seductively for the guys while she changed into something more comfortable. The guys sat in their chairs and I swayed for them, massaging my new breasts and rubbing my ass occasionally. Ann came out a few minutes later and sat down on the couch. She was dressed in jeans and a t-shirt. I could see her nipples poking through as she had decided against a bra. She waved me over and demanded a lap dance. I shook my ass in front of her, then straddled her hips and began grinding into her. I actually thought I felt a bulge in her jeans and I rubbed my bare ass against the fabric of her jeans. I turned over so I was lying on top of her, then made so that I was faking riding her.

Then I felt her reach down and unzip her pants. To my surprise, I felt a plastic cock fall against my ass cheeks. I looked back to see her pull out a tube of lube from her front pocket and begin to cover her cock. She told me to turn back around, but in my moment of viewing I deduced that it was a black strap-on dildo and must have been about seven inches long.

Ann began to hike my skirt up and Mark shifted around in front of me. She told me to spread my legs so that I was straddling her legs, causing my skirt to stay all the way up. This also gave Mark a perfect view as I felt her slide my g-string to the side and stick a lubed finger into my ass. She worked it in and out for a minute or so and I felt my cock stiffing slightly. Chris joked that I must have liked being penetrated.

Then Ann pulled her finger out and ordered me to shift back so that the tip of her cock was directly below my now well-lubed ass. I did as ordered and felt the large plastic head meet my tiny hole. Then she commanded me to keep my eyes on the camera while I rode her cock. I looked up at Mark and slowly began lowering my weight down onto her pole. It took a long time with many upward reversals, but I finally buried all seven of her inches all the way inside me. Once there, I just paused for a moment until Ann smacked my ass hard and told me to fuck.

I started rising back up so that her shaft was only a third of the way inside me, then lowering myself back down to two thirds. I kept this up for a while as sweat started slowly dripping down by back. I could feel myself starting to get flushed as I worked her plastic cock in and out of me. I was relieved when Ann ordered me up off her and into the dining room because my legs were also starting to get tired.

Once in the dining room, Ann backed me into the corner of her long wooden dining room table. Then she pushed me back so I was lying out along one of the sides with my ass on the edge and my legs up. She wrapped her arms around my legs, shoved her cock back inside me, and started pounded me. When I was riding her, I was definitely taking my time. On my back, this was a completely different feeling as she took long, fast, hard strokes deep into my ass. I started to notice myself reacting with every inward thrust by letting out a little whimper. Mark had come up beside the table to get a close up on my face as I would let out those little sounds. I just stared up into the camera and could imagine the image of satisfaction I must have had as Ann slammed her cock seven inches deep into me on every thrust.

Then Ann asked if I liked taking cock inside me. I just smiled and nodded. She pointed out that I had another one right by my face, Mark's. Taking her cue, I reached over and unzipped his pants as he remained motionless, the camera aimed at my face. I pulled his limp cock out through the hole in his boxers and began to stroke it. He was a little distance away from the table, so I reached around his waist with my right hand, and then leaned over as he neared and took his head into my mouth when it got close enough. I held him tight against the table and started to circle his head, then backed off and licked down the underside of his cock. I swirled my tongue back up to his head and took him back into my mouth. Then I started pulling my head left and right until his cock met the back of my cheek to the edge of my lips.

Ann had kept pummeling my ass and it now felt raw. She said something to Mark and a moment later I felt him pull his cock out of my mouth and shoot his cum all over my face. The first load flew right past my mouth and landed on my cheek, some even hit my ear lobe. The next shot was more accurate, but still off the mark as it landed on my face just next to my nose. One last little dribble found its way to my chin. I looked down at Ann and saw her holding the camera, her full weight buried against me and her cock slammed deep inside me for that whole incident. Mark kept his cock above me and shook it clean, each time spraying my face with small ropes of his cum.

Ann told me what a whore I was, then pulled her cock out of me. She handed the camera back to Mark and then pulled me up off the table. She led me back into the living room where Chris had passed out watching Sports Center. She commanded me to unzip his pants also and start sucking him off. Once Mark had pulled his pants back up, she told him to stand behind Chris and film the action. She told him that if I took my eyes off the camera to let her know.

I dropped to my knees in front of Chris, cum dripping down my face and falling between my tits. I unzipped his pants and pulled his cock out. I felt him stir groggily as I took him into my mouth. Ann joined the action a moment later as I felt her spread my legs apart and shove her cock back inside me. Chris just looked down at me blankly while I stared past him, bobbing my head up and down on his cock.

At one point, I took his cock out of my mouth and looked down while tonguing his balls. I heard Mark notify Ann of my lack of eye contact. She called me a dumb slut for not being able to obey directions then added more lube to her cock. She told me she was going to punish me ten times and I was to count each punishment. I was a little confused until I felt her pull her cock most of the way out of me, then smack my ass hard with what felt like a riding crop. I squealed like a little girl and then she slammed her cock deep inside me while I clenched my ass tight from the pain. I audibly moaned then said the number one. I felt her pull slowly out, followed by another smack on my other cheek. I squealed again, then got drilled to the hilt. I moaned louder this time and then panted out the number two. I managed to keep my eyes on the camera during the first two whippings, slowly stroking Chris' erect cock.

Ann continued beating my ass as I continued squealing like a girl and moaning like a whore. Halfway through, Chris got bored with my hand job and began smacking my face with his cock. Once Ann had counted to ten, she asked Chris if he wanted a piece of me. He nodded to Ann, stood up, and then pulled me to my feet. He led me over to the couch and pushed me back. I sat down, but then he pulled my ass out so that it was on the edge. He grabbed my legs, positioned my ankles so they were over his shoulders, and stuffed the head of his cock inside me. Then he fell forward and put both his hands on either side of my head. His body weight forced my legs tight to my chest and my ass to lift off the couch. With his weight pressing down, Chris had buried his eight inch cock all the way inside me on the first thrust, causing me another girly whimper.

Ann sat on one side of me and told me to say all kinds of nasty things. I remember telling myself I was a fucktoy, a cumdumpster, a cock pinata, and a dirty whore. Mark was seated on the other side videotaping the whole episode. Meanwhile, Chris pistoned in and out of me, driving his cock down and smacking his balls against my sore ass cheeks. Ann grabbed my hands and put them on Chris's ass and made me feel the muscles contract when he had driven into me. With my legs on either side of my head, I was forced to stare up at Chris while he fucked me hard. He stared back down at me, leaning forward occasionally to stick his tongue in my mouth and kiss me passionately.

I lost track of time as I continued to be Chris' piece of ass, but felt myself getting really hot as he fucked me hard and kissed me for an extended period of time. I was gripping his ass tight and moaning with pleasure. Then he drove his cock all the way inside me and flooded me with his cum. This put me over the edge and I felt myself cum into my g-string, both of us spasming wildly.

Chris stayed on top of me for a minute longer, and then pulled his cock out of my ass with a pop. My legs fell to my sides, displaying my distended ass for Mark and his camera. A drop of Chris's semen had slipped out when he pulled out and sat on the edge of my ass. Otherwise, the rest was still pooled deep inside me as I remained angled back, with my ass up in the air.

Ann got up and went into her room. At the doorway, she pointed to Mark and told him to come into her room for the night. I shifted so I was lying down on the couch, repositioned my g-string, then Chris came and joined me. He wrapped an arm around my waist and we lay spooning until I fell exhaustedly asleep.

Midway through the night, I felt Chris shift slightly. He had one arm under my neck and wrapped across my chest, the other had been on my hip when I slept. I could feel his free hand lifting up the back of my dress. He exposed my ass, then grabbed my g-string and pulled it back to the side. I felt the tip of his cock press against my fuck hole as he put a hand back on my hip.

Much to my surprise, I had actually enjoyed the fucking I had gotten earlier. As I lay there realizing that Chris wanted to be inside me again, I got very turned on. I reached over his free hand and put my hand on his ass and pulled him tighter to me. He also pulled on my hip and I felt his cock head inch inside me. I lifted my left leg and felt him grab it behind my knee and pull it upwards, exposing my ass even more. He then slowly buried his cock back to the hilt.

He started to fuck me again, this time much slower than earlier. He took long slow strokes, pulling almost all the way out before driving completely back in. He gripped me tight to him with the arm I was laying on, holding onto my left breast with his right hand. I started to moan again lightly with each penetrating thrust. He fucked me this way for a few more minutes, and then rolled us over so he was on top of me with my face buried in the couch. I felt him pull out and pull himself off of me, and then I felt both of his hands on my hips. He pulled my hips back until I was on my hand and knees and then he reentered me. He fucked me hard again and I could feel our balls touching on every inward thrust. I could also feel my ass cheeks jiggle every time his hips smacked mine.

I had my head down while I was being pounded and didn't notice Mark approach the couch. He sat down in a way where I had to move my hands to accommodate his naked body. Then leaned back and I saw his erect cock pointing right up underneath my mouth. I didn't waste any time and dropped down onto his shaft. For the second time that evening, I had a cock in my mouth and one in my ass. This time, however, they were two real cocks and the thought made my own cock stand firm.

Chris continued his assault on my ass and I worked Mark's cock with short fast strokes in my mouth. A few minutes later, Chris pulled out again and I felt him sit down on the couch behind me. I felt hands on my hips again as he pulled me back and to the side until I was riding him reverse cowgirl. I had both my legs bent uncomfortably underneath me as Mark stood up and walked in front of me. He guided his cock back into my mouth as I put both hands on his hips for stability. I began to ride Chris' cock up and down, which also caused me to take Mark in and out of my mouth.

I found a good rhythm and fucked Chris nicely. About five minutes into my cowgirl antics, I felt Chris shoot his load into my ass for the second time. Mark followed a few seconds later, but this time he held my head onto his cock and made me swallow his cum. I gulped it down and then looked up at him as he pulled his cock out of my mouth. He held it in front of me to clean and I licked it dry.

It was at this moment that I saw Ann, again with the video camera and a devilish smile. She told the boys to leave after they got cleaned up because I was going to need some rest for the long day we had ahead of us tomorrow. But that is another story...

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