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Yesterdays Dreams by: Patricia Anne Anderson
Somethings happen that we dont relay expect and in my case it was totally unexpected. My girlfriend and I tried something one day and it turned out that I liked what we did. So much so that I do it on a regular basis now and she and I enjoy these sessions very much. We have even invited some of our friends to join in.
It was a Sunday afternoon and as far as the day was going like any other Sunday we spent together. My girlfriend Carole and I were watching a show on Television about Transsexuals and Crossdresseers and she looked over at me.
"Gee Patrick, I wonder what you would look like dressed up, you do have the small size and everything.
I just looked at her funny. Yes I was rather small for my age of 19, she was 18 and as tall as I was. I was only 5 6" tall and weighed all of 130 Lbs. I started to say something and she started to plead with me.
"Oh please Patrick, please lets try this just once."
"Well OK honey if you want to."
"Great lets go into the bathroom, there are some things I need to do."
I followed her to the bathroom and she told me to get undressed while she prepared a bath for me. She started the water and then put some rose scented bubble bath in the water. I didnt mind because I took a bath with her every now and then and I loved the bubbles. She took out a bottle of Nair and began applying it to my body. I waited the required 15 min and then stepped into the bath. The minute the water hit my skin all my hair fell off. I felt sort of funny but Carol told me that it was natural and that my skin would be baby smooth. It did feel different as I noticed and actually felt good.
Carol took off her clothes and got into the bath with me. This aspect I loved and we kissed. As she kissed me I got an instant hard on and she told me to sit down and she would take care of it for me. She straddled my legs and as my cock sank into her warm pussy I almost went crazy. The feel of my smooth skin next to hers was a real turn on. I could not help myself as we both came to a crashing orgasm.
"There that should take care of that my love." she said with a smile.
"It most certainly did sweetheart."
She washed me all over and when she picked up my razor I wondered what she was doing. She put shaving cream around my pubic area and expertly started to shave my pubic patch into a heart shape like hers. I couldnt help but admire the way it looked. She also shaved all the hair off of my balls. So I was hairless even there and it felt funny. She washed my shoulder length hair and put cream rinse in it to make it soft. I kept my hair long because Carol liked it that way. When I went to work I would put it in a pony tail so it wouldnt get in the way. But at home I kept it down. Carol continued to fix me up as she said. When we got out of the bath she took my hand and we went into the bedroom.
I had a towel wrapped around me like she did and one on my head the same as hers. She sat me on the bed and went to her dresser to get several things out. I noticed that she was taking out a corset that she had gotten when she got a bit overweight. It was made of white satin and had hooks in the front and laces in the back. She told me to stand up and she wrapped it around my waist. She attached the snaps in front and started to pull the laces in the back. She told me to stand up and raise my arms over my head. When I did she pulled the laces even tighter. I could hardly breathe and my waist was down to almost 22 inches.
"There that ought to do the trick." she said with a smile.
"it certainly does my dear but I can hardly breath."
"Well you will get used to it in a while sweetheart believe me."
I had no reason to dought her as she knew what she was doing. Next she had me lay flat on the bed with my legs spread. She took my balls and pushed them up inside me and did the same with my cock. It hurt at first but then I got used to it. She took some clear surgical tape and put it on me securing everything in place. She even fashioned a make shift vagina out of the skin from my ball sack. If you saw me you would swear that I had a real vagina. It was actually cool and I was surprised that Carol knew how to do all this to me. She picked up a pair of nylons and told me to hold out my legs and she rolled them up and attached them to the garter straps at the bottom of the corset. They were black and very silky with a lace top the ones I had seen her wear on many occasions.
Next came a pair of red silk panties and when she pulled them up around my waist they were high cut and they fit remarkably well. I started to get turned on and it was hard because my cock was tucked up inside me it couldnt get hard and it hurt. I kept getting these feelings and I was wondering, what next? I soon found out, Carol took what looked like gel sacks out of her dresser and applied something to them. Then she put them on my chest and to my surprise I had two very real tits with pert nipples.
These are silicone breast forms honey, they will not come off as I have glued them to your chest with spirit glue. They will warm up to your body temperature and after a while will feel as natural as mine are to me. You will also note that when you pinch the nipples you will be able to feel it."
I did as she told me and sure enough it felt like I was actually pinching my own nipples and rubbing my own breasts. I wondered where she had gotten them but wasnt going to ask. She picked up a bra that matched the panties and she had me put my arms through the straps and hooked it in the back. It was an underwire push up type bra and it really gave me a cleavage that any woman would die for. She smiled at her handiwork and took my hand. She led me over to the vanity where she sat me in the chair.
She took the towel off of my head and put rollers in my hair. She sprayed on some setting gel and then picked up her liquid foundation and started applying it to my face. The base being done she picked up her compact with powder in it and applied that also. Next came the blush to my cheeks. She put lip liner on me and applied dark red lipstick. The kind that says come fuck me. Then came the eye liner, I was kind of fidgety and she poked me in the eye several times.
"Come on honey sit still please while I put this on."
I sat as still as I could while she finished and then she put on dark eye shadow and mascara to my eyelashes. She began to pluck my eyebrows to narrow them and it smarted for a while. That being done she applied some eyebrow pencil to them to highlight. I sat as still as I could. She took the rollers out of my hair and combed it into a female shape and then turned me around. The person I saw looking back at me was not me. What I saw was a beautiful woman. She kissed me on the cheek and led me back to the bed where she had one of her slinky red dressed hanging there. She told me to step into it and she zipped it up the back. It was a short dress that barely covered the tops of the nylons I was wearing.
Next she put a pair of her high heeled shoes on my feet. They had an ankle strap and when she hooked the straps she told me to stand up. I had a rough time walking because of the 5" heels. She helped me walk in the tight dress and shoes. Then she led me to the full length mirror. I could not believe what I saw. The most beautiful woman I had ever seen was looking back at me.
"There now we are ready for our date." she said
"What do you mean date?"
"Well I called a couple of friends and they are on their way over here now."
"What?" I exclaimed.
"Well I just thought it would be fun dear."
"You mean a date with men?"
"Yes a couple of men I work with, they dont know you and the way I have you made up they will never know."
I was perplexed when she said this, I relay didnt expect anything like this to happen. But as she explained things further I went along with it. She got dressed in a similar outfit while we waited and to all the world we were just two woman getting ready to go out for the evening. We waited about and hour and then there was a knock on our door. Carol went to answer it and in walked two of the tallest and most handsome men I had ever seen.
"Come on in Brad and Albert, we are expecting you."
"This is my sister Patricia that I told you about."
"Hello gentlemen." I said in my sexiest voice that I could muster.
"Brad, Patricia will be your date for the night."
"Albert is my date."
Brad came over to me and took my hand and kissed it. I thought that was very sweet of him seeing as how I had never done this before. I did not know where this evening was going but I had a slim idea.
"Well where are we going?" asked Carol.
"We are going to Chei louise." said Albert.
"Oh that is a nice place." I said.
"Yes it is and it will be fun." said Carol
Carol handed me a purse that she had made up for me and we all left. Arm in arm I went on with my date. He was a real gentleman as he opened the door for me and everything. I got in using the tricks that Carol had instructed me to use. When he got in he wanted me to move closer to him so he could put his arm around my shoulder. I slid next to him and I was really starting to like this. He put his arm around me and let his hand slip down a little and rested it on my right breast. I didnt try to move his hand because I remembered what I used to do with Carol when we went out.
The drive to the restaurant was quite a ride. I could tell that Brad was getting rather turned on because he kept looking at my legs. The dress I was wearing rode up my legs and exposed the top of my nylons. He smiled every time he looked at me. When we got to the restaurant he opened the car door for me and then he did something that I was not prepared for. He bent down and kissed me tenderly on the mouth. I didnt know what to do so I just kissed him back.
He took my hand as I got out of the car and then he put his arm around me. We went in and met Carol and her date. We had a table for 4 right next to the dance floor and after we ordered dinner Albert ordered drinks for all of us. When the waiter came over he asked both me and Carol for ID. I was really scared at this time because I didnt have any female ID and I was under 21 anyway. But I didnt count on Carols resourcefulness. She told me to check my purse and as I did I found an ID card with my picture on it, my female picture. I showed the waiter and he seemed satisfied and went to get our drinks. I had a Vodka Gimlet which was a good drink for a woman. Brad had a martini. I didnt drink all that much and after one drink I was a bit tipsy. Carol laughed as I felt Brads hand on my the under the table.
Dinner came and I ate slowly as Carol did, I did what she did, I wanted to pull this off. Little did I know that Carol had told the men all about me. After dinner Brad asked me to dance and this really threw me off. I had never danced with a man especially while wearing a dress.
"I dont dance very well Brad."
"That is OK Patricia, just follow me."
We moved to the dance floor and there was a slow dance playing. Brad took me in his arms and started to slowly move around the floor. He was really a good dancer and I followed him as best as I could. I laid my head on his chest and he pulled me close to him. I could feel his maleness between his leg as we danced and it was sort of turning me on. Damn what is happening to me? I thought to myself. I am real starting to enjoy this whole thing.
Brad pulled me closer and moved his hands from the small of my back to my rear and started to squeeze it and rub it. Oh my god what was happening to me? I actually let him do this to me. Where was my mind? what am I thinking? I was liking this attention the kind I showed towards Carol. Oh well I decided to let thing proceed as they were.
Carol looked over at me and smiled. She winked at me and flashed a knowing smile my way as her and Albert danced. Brad and I danced several times to slow dances and even to some fast dances. I was really having fun and I knew Carol was too. I love Carol so I went along with this whole charade. When we sat down again there was another drink for me. I sipped it slowly and still I got more tipsy. It was getting late and Carol said she wanted to go home. She and Albert left before me and Brad.
On the ride home Brad was holding my hand. He placed my hand on his leg and then moved it to his crotch. I could feel his cock throbbing as I laid my hand on it. Now what do I do? does this guy expect me to have sex with him? The aspect had crossed my mind when I was younger of having sex with another man but that was just a thought.
This was here and this was now. I was in a situation that I had let my girlfriend lead me into. I just relaxed and let my hand rest on Brads crotch. He seemed to like what I was doing. I started to rub him there gently and tried to do it like Carol did it to me when we were alone. He started to moan a little and he was really getting antsy so I stopped.
"Damn Patricia, why did you do that?"
" I dont really know, I thought you would like it."
"Well I did, and you can keep doing it if you like."
I didnt know what to say, I put my hand back on his leg and we continued to drive home. When we got there before he let me out of the car he took me in his arms and kissed me. All I could do was to open my mouth and let his tongue slip in. I let him explore the depths of my mouth as my tongue wrapped around his. I couldnt believe this, I was responding like any woman would sexually to his kiss and it was making me feel good. Where would all of this lead to?
He let me out of the car and took my hand. When we got to the front door he again took me in his arms and kissed me only this time I put my arms around his neck and put one of my legs up behind me like I had seen Carol do so many times with me. I was really starting to enjoy myself.
When I opened the door I heard Carol and Albert in the main bedro9om and they must have been having a wonderful time. The thing was I smiled and was happy for her I knew this might happen. Carol had always been sort of kinky and that is one reason I loved her. Brad and I sat on the couch and started kissing and hugging. I was by now really getting into this role.
Brads hand wandered to my right breast and as he massaged it I could actually feel what he was doing. It was getting me so excited then all of a sudden I started to shudder and I could feel something deep down inside. I was actually having an orgasm from his manipulation of my breasts. I started to wonder what it would be like to have real breasts.
He kissed me deeply and was French kissing me to boot. And the thing that really got me was I was responding ever so much. Brad started to unzip my dress and I didnt even complain. He took my dress off and I let it fall to the floor. We stopped kissing and I knelt on the floor between his legs. I did something that I thought I would never do. I started to undo his belt and trousers. I pushed them to the floor and reached inside his undershorts and took hold of his huge cock. It was already getting hard in my hand and when I p0ulled it out and looked at it I almost fainted. This thing was a monster, 9 or 10 inches of hard male cock staring me in the face. It was so fat I could hardly get my hand around it.
Dispite this, I started to kiss his cock and as I did I licked his balls and massaged them. He was going wild as I did this.
"Oh baby, kiss my cock, lick it all up and down."
I did as he told me and soon I could see a pearly drop of pre-cum at the tip. I licked it off and it didnt taste all that bad. I opened my mouth as far as I could and took the tip in. It was huge and I had a hard time with it but I managed. I couldnt help but think to myself.
"How could any woman take this thing inside her?"
I got half of it in my mouth and that was all. Brad put his hands on my head and held me there as I started to bob my head up and down. as I did I got more and more of this monster in my mouth and finally all of it. My cheeks were stretched to the limit and when he tried to force it down my throat I nearly gagged. He backed off and let me do what I was doing.
"Yes baby, suck my cock, suck it all, that feels so good."
I was trying my best as I sucked harder while using my tongue on the sensitive underside. He was going into over drive as he started to fuck my mouth. It seemed like forever but finally he got stiffer in my mouth and his cock seemed to grow bigger.
"Yess I am gonna cum baby, drink my cum, swallow it all."
I didnt know what to do at this point as I felt the first blast of his salty man fluid hit the back of my throat. To keep from drowning I swallowed as fast as I could. Surprisingly I didnt lose one drop. I could feel it slide down my throat and I could feel his cock throb with every blast of cum. I let his cock slip out of my mouth and just held the head in while he continued to cum. There was so much that it made my cheeks balloon out as I swallowed all of it. Finally he was done and I cleaned off his cock and let it slip from my mouth.
"Damn Patricia, that was the best blow job I have ever had." he said as he stuffed his cock back into his undershorts.
"Thank you Brad." I said as I smiled at him.
"You are one mean chick Patricia, where did you learn to do that?"
"It just came naturally Brad."
I didnt want to tell him how I knew what he wanted. But I didnt realize that Carol had told both me about me and that it would be fun to see what I would do. She got her wish as Brad and I stood up and walked to the bedroom. In the spare bedroom Brad laid prone on his back while I sucked him to hardness again. I reached over to the nightstand and pulled out a tube of KY Jelly and handed it to him.
"Here Brad, please fuck me." I said with a come on look.
"That I will certainly do my dear."
"Brad be gentle please, I am a virgin you know."
"Yes I know sweetie, Carol told me all about you."
That was revealing news to me as I looked at him.
"Yes I know you are her real boyfriend and she did this to see what you would do and I guess she found out."
"Yes she did Brad, now pleas fuck me."
Brad rolled me over on my stomach and put a pillow under me. Then I felt him putting the KY inside me and around my virgin asshole. I knew it was going to hurt and I didnt know if I would be able to take his massive member. He put the head to the opening and started to push in.
"Oh my god, I screamed." as he pushed the head in.
"It hurts Brad, it hurts."
"Yes it does baby, but in a minute it will be just fine."
I didnt believe him as he pushed more of that monster inside me. It felt like he was pushing a telephone pole inside me and it hurt. He continued to push forward and I gritted my teeth and grabbed hold of the covers on the bed. The tears were starting to come now as I thought he would split me in two. Farther and farther he shoved into me and I was in pain. But he was true to his word, as I felt his balls hitting the backs of my legs I knew he was all the way in. I shut my eyes and just waited. He started to withdraw and it felt like he was taking my whole insides with him. He got out as far as the head and then started back in. After a few minutes it started to feel better and actually felt good.
He continued to fuck me and as he pushed against my prostrate I became more and more excited. I started to shudder and I was actually having an orgasm. It felt good and I screamed at Brad.
"Fuck me, please fuck me deeper, oh it feel so good."
He pounded into me and it was like there was no stopping. I had another crashing orgasm as he fucked me.
"Oh god I am cumming, I am cumming, fuck me."
It went on it seemed like forever I was in an obvious state of ecstasy. Brad continued to slam into my ass harder and harder and it felt like his massive member was going to go completely out my mouth. He was now fucking me at jack hammer speed and I had another orgasm.
"Oh god, fuck me, fuckkkkkkkkkkkk Meeeeeeeeeee." I screamed.
It wasnt too much longer and I felt him push all the way in and he got stiffer, his cock seemed to expand to twice its size and he screamed.
" I am cumming, take it all baby, take it all."
"Oh cum inside me Brad, fill me with your love fluid, fill me all the way."
Blast after blast of his hot sticky cum splashed into my bowels. It seemed like he had a gallon of the stuff as spurt after spurt shot up inside me. I was in ecstasy as I had yet another orgasm. When he was done he collapsed on top of me and as his cock came out of me I rolled over and kissed him.
"God Patricia, that was just mind bending."
"Yes it was for me also Brad, you are so good.
We held each other for the longest time before we noticed that Carol and Albert were standing at the bedroom door and Carol had the video camera. She had taped the whole thing and even our session in the living room when I sucked Brad off.
"Damn Patricia, I should have done this allot earlier. You are really good and I think Brad likes you."
"That is an understatement Carol, she is better than any woman I have known."
I had to laugh because I knew this was the first time I had ever done this. I knew now that Carol and I had to do allot of talking. I went to sleep that night with Brads cock inside me. He was curled up behind me and I was happy.
Carol and I are now living as two woman. She has me on female hormones and my real breasts are growing. I am scheduled for breast augmentation in a few weeks and who knows after that. Maybe I will have the operation and become a complete woman. Brad and Albert come over on a regular basis and I love the feel of Brad inside me. I have even had both Brad and Albert at the same time but then that is another story.
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