I am sitting in the living room waiting for my date to show up. A date arranged by my wife Gwen. I am dressed in a slinky red dress, underneath my torso is encased in a white corset which reduces my waist to a mere 25 inches. On my legs are a pair of black nylons attached to the straps hanging down from the corset. The tight white panties are holding my testicles up inside my body and my penis back between my legs. On my feet are a pair of red ankle strap shoes with a 6 inch heel. I am wearing a auburn colored wig that reaches down to the middle of my back. My make up is done meticulously. I wait nervously as my wife Gwen putters around getting ready for her date. Just how did I get in this position?
It all started about 4 years ago. Actually my interest in female clothing began when I was age 7. I was born an only child and my father died very shortly after I was born in an automobile accident. My mother tried her best to raise me as a boy but she just couldn’t. When I was 7 I started experimenting with my mothers clothes. I would dress up and play house wife. I even got to like cleaning the house and cooking dinner when I was a teenager. My mother loved it and soon afterward she began to teach me how to cook. All through highschool I wanted to be a female as much as I could.
My mother did her best to encourage my dressing but she didn’t want me to be a real girl. She love the fact that she had a son who could relate to his female side. After I graduated highschool I went to college and my crossdressing was put aside. The urge was there to dress but I just didn’t because of my friends. I met my wife Gwen in our senior year and we quickly fell in love. We were married right after we graduated and I was in no big hurry to share my desire with her. That all changed 3 weeks ago when she came home from work and caught me dressed in a skirt and blouse.
To my surprise she did not get mad at all. She just came up to me and kissed me and smiled.
"So I see you have finally decided to follow your passion dear."
"Ahhhhh, I don’t know what to say, you aren’t mad at me?"
"Of course not sweetheart, your mother told me a long time ago and
I have just been waiting for you to tell me, but this is just as good."
I just sat there looking at her with a blank look. Then a smile came to my face. I stood up and took her in my arms and kissed her.
"So my dear husband lets explore this farther."
"What do you mean Gwen?" I asked.
"Well I would like to see just how you would react when confronted with the situation of being with a man."
"But honey I am not gay."
"I didn’t say you were honey but it would be interesting."
"Are you daring me too?" I asked.
"Yes in a way I guess." Said Gwen.
"And then what if I like being with a man?" I asked.
"Then we will explore your sexuality farther my dear." Said Gwen with a smile.
We sat and discussed the options for a while then Gwen took my hand and led me to the bedroom. She told me to get undressed and she went into the bathroom. I heard the water running and she came back out.
"I am running a bath for you my dear, I want you to go in and before you get in the bath water spread this all over your body."
She handed me a tube of depilatory and helped me spread it all over myself leaving a little triangle patch of hair just above my cock and balls. I waited the required 12 minutes and stepped into the bath. When I laid down in the water all my body hair came off. To my surprise she joined me in the bath. Now Gwen was a very beautiful woman and her size 36C breasts were sticking out at me. I couldn’t control myself and neither could she. I was instantly hard and she straddled me right there in the bath and we made love.
If you have never made love in a bathtub it is a real experience. Gwen was like a wild woman as I sank my cock into her tight vagina I nearly shot my wad right there and then. I held back as she fucked me and when I did cum it was like a volcano erupting. I nearly passed out from the sheer pleasure. My smooth body rubbing against hers was fantastic.
We got out of the bath and Gwen toweled me off. I had to admit that this new twist to my crossdressing felt good. She took my hand and led me to the bedroom where she sat me on the bed. I was puzzled as she went to the closet and took out some clothes. Then she went to her dresser and took out some panties and a bra. She also took out one of her satin corsets.
She laid them on the bed and then turned around and gave me a kiss on the cheek. As she puttered around the bedroom I sat there watching her and she was smiling.
"Now Patrick my dear we are ready." She said.
"Ready for what dear?" I asked.
"You will see honey." She said.
She picked up the panties which were a dark red and satin. She slipped them up my legs and around my waist. She smiled as she stood back to observe what they looked like.
"Hmmmmm, we will have to do something about that bulge." She said as she touched the front of the panties.
They were a pair of her panties and they fit like a second skin they were that tight. She had me pull them down and she took my balls and stuffed them up inside my body cavity. It hurt a bit but I didn’t mind at all as she took hold of my cock and pulled it back between my legs. Then she pulled the panties back up and smiled.
"There that should do the trick." She said with a smile.
I looked down and saw that I was perfectly flat just like any girl would be. It actually made me smile and I had to look in the mirror. As I stood there looking in the mirror I saw a flash and there was Gwen with the Polaroid camera in her hand and a fresh snapshot. I just stood there and smiled as she snapped another picture.
"We have to have a record of your transformation honey." She said.
She set the camera down and picked up the lacy matching bra. She had me put my arms through the straps as she hooked it in the back.
"Something is missing here." She said with a smile.
I stood there watching as she went to her dresser and pulled out a small box. She opened the box and took out some perfectly formed silicone breast forms. She came back over to me and held them up. She took the straps of the bra off my shoulders and set the fallacies down. She picked up a tube of something and spread it all over the back of the fallacies. They felt cold as she pressed them up against my chest. She smoothed them down and when she stepped back I had a pair of real breasts protruding from my chest. They looked so natural and you couldn’t tell that they weren’t actually me. She picked up the camera and snapped a picture. I couldn’t help but admire the breasts as they stuck out from my chest.
Gwen had me put the bra back on and sure enough it fit perfectly. I smiled as she snapped yet another picture. She set the camera down and picked up the satin corset. It was black and when she wrapped it around me she told me to raise my arms as high as I could. She snapped it in front and then moved to the back. She began to tighten the laces and as she drew it in my waist started to shrink. When she was done I could hardly breath but my waist had been reduced to a mere 25 inches. As I stood there she snapped another picture. After a few minutes I got used to the tight constriction of the corset and Gwen set about to finish her task.
She had me sit on the bed as she rolled a pair of silk stockings up my legs. The stockings were black and they went with the red bra and panties perfectly. I didn’t need a garter belt because these stockings had the lacy tops that had elastic on them which held them in place. She picked up the camera and snapped yet another picture. I was beginning to get into this it was much more fun than doing it by myself.
Gwen took the red dress off of the hanger and had me step into it as she did I noticed that it fit perfect and it fell down on my body and fit like a glove. As she zipped it up the back she stepped back and smiled as she picked up the camera again. The dress was a mini and it barely covered the tops of the nylons. I couldn’t believe how nice my legs looked as I stood in front of the mirror. Another picture was taken and she had me sit at her vanity. She applied a light base coat of make up and then smoothed the facial powder on. She applied a light coat of eye liner and mascara which highlighted my eye lashes. She put a light coat of blush to my cheeks and some dark red lipstick to my lips. I wanted to look in the mirror but she told me not yet. She went to her closet once more and took out a long curly wig it was auburn in color and as she attached it to my natural hair she let it fall down around my head. It reached halfway down my back and actually felt like my real hair. She combed it out and then told me to look in the mirror.
I couldn’t believe what I was looking at. There staring back at me was the most beautiful woman I had ever seen. All my years of crossdressing had never produced this effect and I could feel the cock between my legs straining to get out. Gwen picked up the camera once again and snapped another picture and she laid it with the others. She took my hand and led me to the bed where she had me sit down. She took a pair of her highheeled shoes and put them on my feet. They had 5 inch spiked heels and an ankle strap. They were red and looked great on my feet. They were a little tight but after a while I got used to them. When I stood up Gwen took yet another picture.
While I had worn heels before I had never worn any this tall before and it took me some time to get used to them. I sauntered across the room and up to the full length mirror on the door. As I stared at the reflection in the mirror I smiled. My dream had been fulfilled the reflection in the mirror was that of a 22 year old female. As I stood and admired myself in the mirror Gwen took more pictures.
"You look very stunning Patricia." Said Gwen.
"What did you call me?" I asked.
"I called you Patricia and that is the way it will be from now on."
"But sweetheart, I am not a girl." I said
"Huh, it doesn’t look like that to me darling." She said
I had to admit she was quite right, I wasn’t the man she married but a woman standing in front of the mirror. She came up behind me and put her arms around my waist and she kissed me on the neck. It sent chills up and down my spine. Gwen went to the closet and took out some clothes and started to get dressed. I went to the living room and sat down. When Gwen joined me she came over and sat on my lap.
"I have always wanted a sister that I could go out with." She said with a smile.
I was dumbfounded as she handed me one of her small purses and a coat. I looked at her and she smiled and kissed me.
"We are going out tonight sweetheart." She said.
"You mean you want me to go out in public like this?" I asked.
"Of course sweetheart, we are going top go out as two woman, and
I think you will enjoy this side of life. It will be a chance for you to experience what it is like to be a woman."
She handed me the purse and we left the house. I was a bit leery about leaving the house but she took my hand and nearly dragged me out. As we drove she kept telling me how much fun we were going to have. I was surprised when we drove up to my mothers house.
"What are we doing here?" I asked.
"I thought it would be nice for mom to see you." She said.
When we got out of the car we walked up to the door I had a bit of doughts but Gwen soon calmed that. When she rang the doorbell my mother answered the door. She smiled as she let us in.
"How are my two lovely daughters doing?" She asked.
"We are doing just grand mother." Said Gwen.
Again I was totally taken aback at the whole situation. My mother talked to me as if I were her long lost daughter.
"There is someone I want you to meet tonight." Said mom.
"And who might that be?" Asked Gwen.
"Well you know how I never wanted to get married again after
Patrick’s father died, well I have met a man and he is very well off and he has asked me to marry him."
"That is great, I am happy for you mom." Said Gwen.
"And what do you have to say Patrick ‘er’ Patricia?" She asked.
"I don’t have anything to say mom." I said.
She told us about her new boyfriend as we all sat there. The door bell rang as we were talking and when mom went to answer the door it was her nes friend. He was a handsome man in his early 50’s. He kissed my mother lightly on the lips and as she took his hand and let him to the couch my eyes nearly popped out of my head. I had seen this man before but couldn’t remember.
"Gwen and Patricia, this is my boyfriend Thomas." Said Mom "Hello Thomas." we said. "Hello girls, he said with a wink.
I was unaware that mom had told him about me and this whole situation was all a set up. He left my mother and came over to sit next to me which unnerved me.
"Don’t worry little one I know all about your secret." He said.
He kissed me on the cheek and I couldn’t help but smile.
"Well are we ready to go?" Asked mom.
"Go where?" I asked.
"Well we are going out to the club tonight." Said Gwen.
Now the prospect of going out dressed like I was didn’t appeal to me at all but I was trapped. We all left my mom’s house and headed for a club that we all would go to when I wasn’t dressed like I was. It was a place that Gwen and I used to go to all the time. I didn’t say much on the ride to the club but mom and Gwen were regular chatter boxes. Gwen and I sat in the back seat and Thomas drove. We got to the club and Thomas parked the car and opened the door for mom and then opened the door for me and Gwen.
Dressed as I was I was leery of getting out of the car but I got out and Gwen took my hand. The club was a hot spot and there were several men there that always hit on new girls and that was what I was afraid of. The doorman looked at me kind of funny and I could swear I heard a whistle but who was he whistling at. We went in and sat down in the back of the club which is what I wanted. Still I was very scared and nervous as hell.
When the drinks came the girl that brought them was wearing one of those skimpy little dresses. Gwen made the comment that she would like to see me in one of those. We all laughed as Gwen looked right at me and I told her not on her life. The grin that she had on her face told me that some time in the future I would be wearing one weather I wanted to or not.
Thomas asked me if I wanted to dance and I reluctantly agreed. He took my hand and I couldn’t help but realize that my hand was so tiny in his and I actually blushed. It was a slow dance and he held me close to him and at one point I swear I could feel that he was getting very excited. I laid my head on his shoulder as we danced and he whispered in my ear.
"You are a very pretty girl Patricia, it is too bad that you are really a man under all that frill and lace."
This scared the hell out of me and I tried to pull away. All he did was to hold me closer and he put his hand in the small of my back and pulled me even closer. What the hell was going on? This was mom’s boyfriend and he was scarring me. When the dance was over he took my chin in his hand and kissed me lightly on the lips. He actually thanked me for the dance and held my hand on the way back to the table. When we got there Gwen winked at me and smiled. I sat there sipping my drink and a strange man came over and asked Gwen if she wanted to dance. I started to say something but decided not to and watched as my young wife went to dance.
Mom and Thomas went to dance leaving me alone. It didn’t take long before a man came and asked if I would like to dance. I reluctantly agreed as he took my hand. I felt awkward as we danced because I couldn’t dance too well in the heels I was wearing but I did my best. The dress I was wearing kept riding up past the tops of my nylons and the guy I was dancing with just smiled. When a slow dance played he held me close even closer than Thomas had.
"My name is Erek and you are very pretty." He whispered.
"Thank you." I said with a smile.
As we danced the slow dance this man held me close and he put his hand on my rear end. He pulled me even closer and started to rub my pantied ass. I must say that I was actually getting turned on by all of this. I could feel his manly tool hardening as he held me close and ground his crotch into me. Admitting to myself I could also feel my own tool getting hard as it was trapped between my legs. After the dance he stood there and he lifted my chin and kissed me hard on the mouth. To my surprise I responded taking his tongue into my mouth. As we walked back to the table he had his arm around my waist. When we got back I could see that Gwen was sitting with the guy she had been dancing with. He had his hand resting on her leg and I could see that her dress was hiked up a bit.
We sat down and the guy I was with did the same as he moved his hand farther up my leg. Mom looked at me and smiled and this really scared me. What was going on her? was this all a set up? I wondered as Erek kissed me once again. It was getting late and Gwen said that we should go but to my surprise she suggested that the men leave with us. Now what was going on? This night was turning out to be very interesting to say the least.
With his arm around my waist I left with Erek. I must admit he was a sweet man and very handsome. He was alt least 6’ 4" tall and very well built with very strong arms. I would not find out till much later that the two men were guys from Gwens office where she worked. We got to the parking lot and it was decided that I would go with Erek in his car back to our house.
What was going on here anyway? What was expected of me? I was lost as Erek opened the car door for me. I got in and he closed the door. As Gwen went with the other guy she winked at me and threw me a kiss. As we were driving back to the house Erek had his hand on my leg and he slowly pushed my skirt up and soon his hand was close to the crotch of my panties.
I tried to move his hand but I was having to much luck. He smiled as we drove but we didn’t turn off of the freeway towards the house. This started to frighten me. We drove for sometime and wound up parking at a local make out spot. I had been to this place when I was a teenager. It was where the teenagers would sit and make out and various other things. He parked the car and immediately pulled me close to him. He kissed me as his hand found my panties. He started to rub the crotch of my panties and I was getting very uncomfortable. But I did respond to his kiss and my hand was resting on his lap.
He kissed me hard and long and I found myself rubbing his cock through his trousers. He was definitely turned on. Then I did something that even surprised me. I started o unzip his trousers and as I did I reached inside his trousers and into his shorts and held his cock in my hand. He was huge, much bigger than my own small tool. I stared to move my hand up and down and he moaned as I did. When we broke the kiss I lowered my head and was looking at the biggest cock I had ever seen.
I kissed the head and there was a drop of precum coming out. I licked the precum from his cock. I ran my tongue up and down his cock and he was starting to wiggle around in his obvious discomfort.
"Why don’t you take it in your mouth Patricia, suck my cock."
I did what he asked as I took his cock into my mouth. It was huge and my mouth was stretched to the limit. He was a good 10 inches and very thick so it took me some time to take at least half of it in. I started to gently suck as he put his hand on my head and pushed it down. I nearly gagged as he pushed more and more of that monster in. By now I was really starting to get into this. What was wrong with me? I had never dreamed of doing this to another man. What was I doing here and what was my wifes plan?
I sucked on Erek’s cock and he held my head down and he moaned as I continued to suck.
"Oh my god, that feels so good, suck that cock, make me cum."
I started to really suck now and used my hand on what I couldn’t get into my mouth. He started to move his hips up to meet my downward motion which forced more of that monster into my mouth and down my throat. I started to gag and he pulled back for a second.
"Just relax sweetheart and let it happen." He said.
I relaxed my throat muscles and sure enough as I concentrated I got his whole cock into my mouth. I started to bob my head up and down and he let go of my hair. He moaned as I swallowed his huge cock. I felt him tense up and his cock seemed to expand. I could feel the cum rushing up the length of his cock but was unprepared for the massive amount that shot into my mouth and throat. There was so much that it ran out the corners of my mouth.
"Oh god, I am cumming, swallow it all, drink my cum." He hissed.
I swallowed as fast as I could and it tasted salty yet it was sweet. I just couldn’t believe that I was doing this. Just what was next for me? Where would all this lead to? Here I was a feminized male in a car alone with another male sucking his cock and loving it. I kept his cock in my mouth until it went soft and as it slid out of my mouth I licked it clean. The cum that had escaped my mouth was on my chin and I scooped it up with my fingers and licked them off. When he had put his cock back into his trousers and zipped them up he sat up to get himself a bit composed.
"That was fantastic, you really know how to suck a cock."
All I could do was smile as he took me in his arms and kissed me. I am sure he could taste his cum in my mouth but that didn’t stop him from French kissing me.
"we better get you home sweetie." He said.
"yes I think that would be a good idea." I said with a smile.
It was well after one AM and I was sure that my wife would wonder what we were doing, or would she? Erek started the car and we headed home. He held my hand all the way and I felt so small and insecure sitting there in the car next to him. When we pulled into the drive at my house there was a strange car in the drive. I thought to myself that it must be the other guy’s car. I would find out that it sure was and my wife had been doing her own thing. When I opened the door to go in Erek followed me. There in the living room were my wife and Shawn the guy that she had met at the club.
They were sitting on the sofa and holding hands. When she saw me come into the room she got up and came to me and kissed me. I kissed her back and she loved it. She took my hand and we both went over to the sofa to sit down. She sat between me and Shawn.
" I think introductions are in order." She said.
"Yes I think so." I said with a smirk.
"Darling this is Shawn Davidson, I work with him."
" Hello Shawn." I said.
"So this is quite an arrangement you have here." Said Shawn.
"And what do you think that is?" I asked.
"Well this lady here told me about you, are you really her husband?"
"Yes I am, and this is the first time we have ever done this."
"Hmmmmmm, you are a guy????? Asked Erek.
"Yes I am." I said.
"God you could have fooled me." Said Shawn.
"Well apparently I did." I said.
"Darling what were you two doing?" Asked Gwen.
"What do you think we were doing, probably the same thing you were my dear." I said with a laugh.
With that the two men said their good byes and I walked them to the door. As we got there Erek patted my behind and gave me a little pinch.
I would love to do this again." He said.
"Well that is entirely up to my wife." I said.
Gwen smiled at me as she joined me at the door.
"Well I think that could be arranged, I will talk to you at work."
"Good, see you Monday Gwen." Said Erek.
The two men gave both of us a kiss and Gwen shut the door. When she shut the door she held my hand and we went over to the sofa.
"I think it is time to go to bed my love." She said.
"Not before you answer some questions Gwen." I said.
"What do you want to know darling?" She said smiling.
"Just what the hell is going on here?" I asked.
"Well your mother told me how when you were young you liked to dress up. I just decided to take it a bit farther is all."
"Well, what do you have planned?"
"You obviously made Erek very happy." She said.
"Well I did suck his cock if that is what you want to know."
"Oh my god honey I never meant it to go that far, not right now anyway."
"Just what do you mean by anyway?" I asked.
"Well I wanted to see if you would like being my husband/wife."
"Well, I did have fun and I will have to admit I liked it."
"Well then you will like the other surprise I have for you."
"What surprise is that?" I asked.
"You will see when we go to bed honey." She said with a smile.
I left it at that but was wondering what she meant. I would soon find out what she meant. When we got to the bedroom she had me get undressed and she went to the closet and took out a box. When she opened the box I nearly fainted. She held up the tiny babydoll nightie and handed it to me.
"Here baby you will wear this tonight."
I took the nightie and put it on and it fit good. I was surprised that it fit me so well. As I got on the bed she went into the bathroom and she was carrying another box. When she came back she was wearing her bath robe. She did all she could to keep her back to me. I wondered just what she was doing. I would soon find out because when she turned around she was wearing a strap on penis and it looked bigger than Erek’s real one.
"Oh my god, what the hell is that?" I asked in horror. "This is your new love toy dear and I have another surprise for you later." She said with a smile.
"And just what might that be?" I asked.
"Now that is a surprise hone, you wouldn’t want me to ruin the surprise would you.?"
"I guess not my love." I said.
She had me lay on the bed on my back and proceeded to give me the best blow job I have ever had. I couldn’t help but stare at the Dildo she was wearing. She sucked me deep and I was going crazy. She stopped just short of me cumming and I was going crazy. She rolled me over on my stomach and had me put two pillows under me. Then I felt her put something cold on rear end. Then I felt her push one of her fingers up inside me. I sucked in my breath as she worked yet another finger up inside me. Then she got on her knees and while holding my ass cheeks apart I could feel something poking at my asshole. She pushed forward and the pain was intense as she forced the head of the fake cock inside me.
"Oh god that hurts honey, please stop." I screamed.
All she did was push in farther as the pain built. I could feel the dildo going in farther and farther. When I felt it up against my ass I knew she was all the way in. She started to moan as she withdrew the thing until just the head was in and then she pushed in again. The pain was intense as she fucked my ass. She continued to do this for what seemed an eternity but after a while I grew accustomed to the huge invader. She picked up her pace and when she did I felt something I had never felt before. I started to quiver all over and I shot my cum all over the bed. Gwen picked up her pace and I heard her moan as she was obviously caught up in an orgasm of her own.
When she was done she pulled the dildo out of my ass and flopped back on the bed. I rolled over and looked at her and she looked at me through glazed eyes. When she calmed down she took me in her arms and kissed me. She got off the bed and picked up yet another box. She opened it and told me to roll back over. When I rolled over I felt something being pushed into my ass. When it was all the way in it felt a bit uncomfortable.
"There that ought to do." She said.
"What the hell is that?" I asked.
"That my dear is a butt plug and you will wear it at all times to keep you nice and loose back there." She said with a smile. "Now roll over and go to sleep."
Despite the discomfort of the thing in my rear I did fall asleep. I had some dreams that would scare anyone. There I was and instead of the silicone breasts I had real ones. I also had a pussy, I dreamt this and woke up several times and had to check myself to see that I was still a male.
When we got up the next morning there was more of the same that happened the night before. After each session the butt plug was reinserted and a harness was strapped to me to keep it in.
That all happened three weeks ago and now here I sit waiting for my date. I know who it is, it is Erek and I think Gwen has something in mind because inside the purse I am holding are some condoms. She told me that I didn’t need them as far as she was concerned but that every young lady carries them. So here I sit waiting for my date.
To be continued:
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