My story is that I am call girl or should I say a transvestite call girl. You can say it was a mutual choice by my wife and me. Yes I am married and my wife helped me become this way. Never in my wildest dreams would I have thought that I would be making money having sex with men as a women let a lone just having sex with men.
It began about six months after we just married. It was a Saturday morning my wife Megan was leaving that day for work at her bank. She is an assistant manager at the bank and had to be there to open up early that morning. Before she left she had put some clothes in the dryer and asked me to make sure I got them out as soon as they were done, so that they did not wrinkle. I kissed and saw her out the door and promised to take the clothes out of the dryer as soon as they were done. She left and I went to go change as I have been doing for last couple of months since being laid off work.
What I mean by change was I would change into Natalie the little house maid, clothes included. Since around eight years old I would wear my sisters and mothers clothes. I started out wearing nylons and progressed into more articles of women's clothing and shoes. As the novelty of just the clothes wore off I turned to more feminine activities like playing house and fashion shows, but only by myself. I had also at this early age would self spank myself with anything that would resemble a paddle; be it ping pong paddle, hairbrush, etc... As I grew older I would play out more roles such as schoolgirl or maid; having to be punished for messing up. I thought I would out grow this desire once I was married.
So, Megan had left for work and I went down to the basement to my hidden cash of women's things. I had only collected a few items since I was married and they were mainly nylons and panties. I picked out a pair of pink cotton panties and pair of suntan pantyhose and put them on, since I did not have any dresses or skirts I wore a football jersey that fell about few inches down my thigh. I went back up stairs to the laundry room as the clothes in the dryer would soon be done.
In the laundry room I was just standing there in my stocking feet and jersey looking out the window as the buzzer on the dryer went off. As I turned away from the window my heart about jumped out of my body my wife Megan was standing just in the door way. She was there hands on her hips, one foot out ninety degrees, and legs apart staring at me. I was at a loss for words. I was in shock because I was caught but also becoming aroused by her stance and the stern look on her face. She was hypnotic with classic pumps on her feet, legs incased in shear nude color stocking, and dressed in a pin stripped dark grey business skirt and jacket. She spoke first saying she had forgotten her keys to the bank. I just nodded. When she turned to leave, she suddenly turned back and said that I looked cute and I had better be dressed as I was when she got back home, with that Megan left.
I was dumfounded should I change back, should I call her, but I decided to do a she said get the clothes out of the dryer and be dressed this way when she got home. In about an hour the phone rang and it was Megan, she wanted to reassure me it was o.k. and she was so horny she can not wait till she got home. Then her tone changed a bit as she told me that the bathroom and kitchen better be cleaned before she got home. I was amazed after I had hung up the phone that I remember saying "yes ma'am" and that she wasn't upset or saying she was leaving me.
It was about the time she should be getting home that I was up stairs cleaning the bathroom as she had told me to do. I was on my knees wiping the tub out I heard her heels clicking on the bathroom tile. She came up next to me and bent down and kissed me deeply on the lips. We never separated as I stood up so we could embrace. I moved her around so her back was to the bathroom counter and lifted her up so she was sitting on it. I got down on my knees and pushed her skirt up above thigh high stockings so I could pull her panties down, but to my surprise they were not there. She then moved her hand out above my head where I looked up and she dropped her panties on my face. She said she removed them because I had gotten her all wet thinking about me in nylons while she was at work. I stood up removed my jersey and pulled my pantyhose and panties down to my thighs. We embraced again kissing as she wrapped her legs around me. I was able to penetrate her easily being she was well on her way. As we made love right there on the counter the feel of our nylon clad legs rubbing together brought us to orgasms in sync and so intense were our orgasms that we almost fell to the floor.
After that we carried each other off to our bed and collapsed. That's where we discussed what had just happened. Before today we had played around with me in her panties for fun, and she really enjoyed it to the point one time when we went out for dinner she had me put on a pair to wear under my clothes. I could never tell her how much I wanted to dress up as a girl then as I did now. So I had told her about my dressing up as a child up until the time we got married. She also reviled to me how much she missed having dressed her next door neighbor. He was a boy around her age that would come over and the played dress up, with full make up and all. About age fourteen he moved away but she still stayed in contact him through college. He became a drag queen somewhere in California doing shows. She said how much she missed it but was also afraid to tell me how much she wanted to do the same thing with me. She never knew how far I would go and never went passed the panties.
We talked more about it and we decided that could give it a try. That instance she said we had to do something about my hairy legs. We set up a bath and started shaving my legs but it went much further. Since I did not have a job just yet we decided it would be fine to shave all of my body hair off. It felt wonderful as she ran her hands all over me getting me hard again and with that we got out of the tub and she dried me off with a towel. While down on her knees she got busy giving me a blow job. I came in her mouth but did not notice she had not swallowed. When stood up she kissed me fully again as she opened her mouth wider she grabbed the back of my head and forced my own seed into my mouth. I tried to back away but gave in just as quick and swallowed it then I tried to get more from her lips.
She stepped back and said, "Wow that was hot" and wanted to know if I like it. I a greed and went down on her.
After getting her off, she wanted to see what other clothes I had, so went to the basement and got them to show to her. She looked at the clothes and nodded her head to displeasure, telling me I need a lot more things. She handed me some panties and pantyhose and told me to put these on as we were going shopping. We headed off to the mall me in my regular guy clothes but with nylons and panties on underneath. While on the way there she wanted to know more about what things I would wear when I was a child. I told just what ever my sister's or mother's stuff I could find. She didn't mean that, she meant what I pretend to be. Such as herself and her neighbor boyfriend did, when they played dress up as cheerleaders or mother and daughter. I told about how I like play school and pretend to get in trouble, in which I would self-spank myself, as soon as I said that she about locked the car brakes up. She pulled into a parking lot reach over and started kissing me all over telling how much she really loved me now and how she thought how lucky it was we had meet. We went over many more things as we continued on to the mall.
At the mall we first stopped to get me some lingerie. Like her I was now going to be a stocking girl with no more pantyhose as we both agreed on that we started selecting a few things. Now it was going to be nothing but thigh highs or stockings with a garter belt. We got the basic colors to start with and decided we could shop on line for much prettier things. Next I would need at least a couple of bras, so she picked out a couple basic ones it was decided I should wait until I got falsies to get better ones. Next purchase was a couple of nighties one basic black satin chemise and one baby doll that was pink. The next place we went to was the young miss department; she picked out couple of schoolgirl type skirts and blouses along with couple of other outfits and dresses. We thought it best if sneaked the clothes into the men's dressing rooms where I had to try them on. Wow it was a real turn on knowing I could be caught and found out but better still it was just trying them on. Then came the shoes, it was little more embarrassing trying them on in the store since there are not any dressing rooms for someone buying shoes. We did get a few looks by other customers since they could see the nylons on my feet then me slipping on shoes trying them out. The sale girl that helped us never batted an eye. In fact she wanted to know what look we were going for, so Megan said "slutty" in which the sales girl smiled and showed us the four and five inch heels. We bought four pairs of shoes from her three for me and one pair for my wife. We had enough for the night and went home.
At home I had to do a fashion show for Megan with my new clothes; I believe she enjoyed it more than I had. The part I loved the most was strutting around in my new high heel and stockings. I really loved the four inch high sandals; they were black with three toe straps, thin ankle straps one above and one below the ankle, and stiletto heels. I could not keep my eyes off of my own feet, with black shear stocking and those tiny straps I felt very sexy. Megan had that look like something was wrong. She told me to take my stockings off and sit at her dressing table. She fumbled around for something and pulled out some bright red nail polish and nail file. My wife then sat on the edge on the bed had me put my foot on her lap and did my nails. Then while we waited for them to dry she put make up on me. I looked in the mirror and could not believe how convincing a women I had become. I was getting real turned on by it all. She then helped me get into a full outfit, it was the schoolgirl look we were going for, slutty schoolgirl look. First I slipped into white nylon panties; they had a solid front panel lacy waist band and a shear back that was see through. Megan then help with the white padded bra with just a little lace trim. The next article of clothing felt so wonderful I could almost cum in my panties. I took out a pair of white shear toe thigh high stockings sliding each one up my shaved legs, it was one of the most wonderful feeling, and the look of my red painted toe nails was under them was exquisite. I then finished dressing putting on my new very short tartan skirt with a white blouse. I wanted to wear my sandals but Megan had me put on the five inch high Mary Jane pumps, I had protested that I did not want to cover my pretty toes. I was made to wear the Mary Jane's.
After finishing off the outfit with the shoes I was made to walk around the bedroom for Megan. My wife complimented me on what a fine looking girl I had turned out to be and she was never happier that this really did happened. I was beside myself too looking in the mirror and looking at my wife knowing how happy we both were at this moment. Megan then stood next to me each of us looking at each other in the mirror smiling. She put her hand on my ass and felt me up. As she was feeling me up she said I needed a name to go with my new look. I could she her thinking then she came up with Natalie, she said she always thought it to be a pretty name and seem fitting. Her hand then found its way up under my skirt and now was rubbing my pantied ass.
While she was running her had under my skirt she told that I shouldn't have talked back to her about the shoes. Megan removed her hand and grabbed my face and looked me in the eye lovingly and said I needed to be punished for it. She told me to go fetch my belt and bring to her. I gave her a look that said what, and she looked back at me with a look that said she means it. So I went to my dresser and pick out a thick black belt for her to use on me. I brought it over to her and handed it to her she accepted it and point to the bed. I turned and faced the bed then bent over placing my hands on it. She used my new name Natalie when she told me to reach back and lift my skirt and lower my panties. As I did I could feel my hands tremble with excitement! I slowly raise my skirt up and over my ass then pulled my own panties down to my thighs. I then placed my hands back on the bed with my ass now exposed for her to whip with the belt. Megan lovely touch the small of my back which made me feel comfortable about what she was going to do next. She lined up and the first stroke landed. It wasn't so bad just a love tap to get me going. She gave slight pause and landed another just little harder. Megan was kind and asked if that was too hard in which I responded with a no ma'am and she laughed. She than asked to let her know when it was too hard for me; since she didn't really want to hurt me. The next lash with the belt landed hard made me jump a bit, but she waited not saying a word. Now she began spanking as hard with the next ten strokes quicker and without pausing in between. Then again she asked if it was to hard I said no please keep going as my erect cock was pulsing and bobbing up and down on its own. Megan could see how horny it was making when she saw what my cock was doing. The spanking continued. As my wife went on she asked me how I would like to be fucked. I did not answer her right away. Megan asked again if I would like it if she fucked my ass as she continued whipping me. I moaned yes with that she stopped and told me to not move.
When she stopped I could see her walk to her dresser and open her panty draw. Megan reached in a pulled out her vibrator and grabbed some lotion from the dresser. She walked back over and placed the six inch long vibrator on the bed were I could see it. I then felt her place one hand on the small of my back again and with the other hand she put one lubed finger to my anus. She moved her finger around my tight hole slowly circling it with the lubed finger. When she stopped circling she placed her finger on the opening and applied slight pressure until in it when in. As her finger slid in I pushed back and it went in up passed her knuckle. Removing her finger and applying more lotion she began to work two fingers in my hole. I moaned approval as she then began finger fucking me. When she was please that I was loose enough she grabbed the vibrator and placed against my hole. Now Megan stood behind me one hand on my hip other hand holding the vibrator she worked in slowly and waited for my anus muscle to relax and it slid in deeper. When I became loose enough for the vibrator to be shoved in and out with ease she turned it on. I was moaning and moving back and forth now trying to get it in deeper and harder. I could now feel my wife tight up against me thrusting her hips along with the rhythm of the vibrator going in and out of me. She fucked harder and faster. She began moaning herself as she was making herself orgasm. When she finally came she pulled back but left the vibrator in place and began to give me a reach around. I was so turned on it felt like I could cum just by her fucking my ass, but when her hand starting stroking my cock I came only after a few strokes. I came so hard the first load hit my chin and on the bed in front of my face. Then the rest of my load was shot all over the bed.
After I had cum from the reach around she pulled the vibrator out. I stood up and we hugged and kissed telling each other how wonderful this day has been. Megan noticed the cum on my chin and what was running down my neck. She then took her fingers and wiped it off. She then offered it to me asking me how I liked the facial. I smiled and grabbed her hand and open my mouth for her to insert her cum covered fingers in. I sucked and licked them clean tasting myself a second time that day. We decided that we were both tired and it was late and crawled in bed together. I stayed in just my panties and stocking and her in just her panties. As we cuddled she would run her feet up and down my smooth shaved and nylon covered legs as we fell asleep. I dreamt of her having a real cock fucking me while tied to the bed. We awoke next morning with her spooning against me.
The next morning we spent talking about what happened the day before while the both of us tried on different outfits. We spent the afternoon making love until we were spent. We both agreed how good the silk and nylon felt against our body when we had sex, it made our orgasms all that much better. When we finished dinner she asked me how I would feel about me sucking or getting fucked by a man's cock. I told her honestly I did not know as I never thought of having sex with men. Megan then asked me if I did like the taste of cum and if I wanted to keep doing that, I said I did and wanted to do that more often. Then she asked about the ass fucking she gave me, I told her it was the best and knowing that she was the one with cock up my ass fucking me made it more erotic. She agreed that she love doing it also and suggested we get her a strap-on dildo right away. After that she grabbed my hand and lead me to the bedroom were she started out fucking me again this time with me on my back, it was wonderful staring into each other's eyes as she made love to me.
Monday Megan had gone to work leaving me all alone. I decided to dress up in some of the new clothes I had just got. I put on some pink cotton panties, suntan colored thigh highs, the white bra, picked out a blue gene skirt, and a pink tee shirt. I pranced around the house doing a little house cleaning. That evening when Megan came home she called for me to tell me she a brought me a surprise. When I found her in the living room she was holding a black bag. She reached in the bag and pulled out a strap-on dildo. It was about eight inches long and looked life like. I looked at it and became quite aroused by it sight. Then she had that look again like I did something wrong. Megan had noticed I was not wearing any make up and mentioned the fact. I was told I was such a bad girl for not looking my best for her when she got home that I was to be punished for it. With that I had to go fetch the belt for her. When I returned with the belt I handed it to her where she folded it in half and tapped the side of her thigh with it. I was then made to bend over the arm of the couch. She lifted my skirt and lowered my panties getting me ready for a good belt whipping. Megan whipped me good and hard with strokes to each ass check five times then five times across both checks, alternating like this what seemed like a half hour. When she had enough whipping me she left the room and came back in with the strap-on on and some lube she bought with it. I was made to get on my knees in front of her and suck off the dildo. When she had her fill of me sucking the dong I was made to bend back over the couch for a ass fucking. My wife fucked me until she had her orgasm and pulled out. I was told to get up and follow her to the kitchen. When we reach the kitchen she had me get her a small glass and hand it to her. Megan then got on her knees and starting sucking me off. Before I could cum she removed her mouth and starting jerking me off, and when I was about to cum she place the glass in front of my cock. She jerked me off into the glass as I watched not knowing what was going to happen next. After I had came, filling the glass with my seed, she handed it to me and told me to swallow it all down. I nervously put the glass to my lips and began drinking my seed as I watch Megan masturbate herself to another orgasm.
That same evening after dinner we did some on-line shopping. We discussed how and if I liked what happened and agreed it was a big turn on. While looking through the web sites Megan stopped on one that sold maid costumes and said I being me would have to get one of those. She said since it did not look like I was going back to work to soon it would be perfect for me. I had the biggest hard-on as I agreed with her that I needed one. She said also suggested I also get another costume that looked like a naughty Dorothy. I wanted to know why and was told at the end of the month we were invited to a Halloween party at her boss's house. I agreed to getting it as I had been to boss's parties before and some of the costumes have been down right dirty and did not think anyone would care what I came as. Next we looked at a site that sold S&M gear I was to pick out the implements that I thought she should be using on my ass. I always love the paddles so we got a nice wooden one, which was twenty-four inched long and picked out a thick black strap to replace the belt. Megan herself wanted to get a cane as she loved it when in the English type movies the headmistress's always used them on bad girls. We finished the night picking out sexy lingerie for the both of us, consisting of garter belts, stockings, panties and bras. I even picked out wigs and falsies. That night when we got dressed for bed in our nighties I was told that I was going to be punished every day when she got home until I learned to dress and keep the house clean to her standards. To which I would be looking forward to.
That is how every day went for the next three weeks. Megan would find something or another to punish me for, be it something not cleaned to her standards or something wrong with my maids outfit. One of the worst spankings was for putting a run in some expensive stockings. The run in the stocking was from the toe to the very top. I was made to measure it and give her the results. I came up with thirty-six inches but she came up with fifty-two when she grabbed it from me and made it stretch fully. To top it off I was to be spanked by each the cane, the paddle, and the strap fifty-two times. Also over this time period my orgasms had been trained. I could not cum by just our love making anymore I needed to be first fucked in my now so called pussy hole to make me cum. My wife had now completely taken control of me literally body and soul.
It was the weekend before the Halloween party. That Friday night we talked more about me having sex with another man. I was living and getting sex more as a women than as a man, so much that, when she brought it up I said that I really wanted to try a real cock. To my surprise she had thought I would say yes and had set up a date that night with one of her employees, Robert, a young gay man that worked the counter. That night I got ready for my so called date. I got dressed in all black from my matching bra, garter belt, and panty set to seamed stockings, a sexy low cut dress with slits at the thighs which showed the tops of my stockings, and my favorite high heel sandals. My wife helped with the make up and nails. I finished off my look with an auburn colored wig. Megan wanted to fuck me right there and then when the door bell rang. She went to go answer the door, I then could hear her talking to Robert, I was thinking about running and hiding. I could hear her call me by my new name Natalie, so I gave up on hiding and made my way out to meet the man that was going to have his way with me. When I reach the living room they were both already sitting on each end of the couch talking. Megan asked Robert what he thought and he said something to the fact that he had never seen something so gorgeous. Megan had me sit in between the two of them as she put her hand on my knee and smiled at me and told me how much she loved me. She then got up to get us some drinks and tried to Robert and I engaged in some small talk.
When Megan came back with the drinks and handed them to us, she told Robert to ask me about who I was going to be for Halloween, I told him about Dorothy. He said he just love the idea and could not wait till he saw me dressed as Dorothy. When my wife sat back down next to me, she started to get touchy feely with me making me even more horny. I was already horny thinking about having a real cock shoot cum down my throat before hand. Robert was watching her do this and started running a hand up and down my stocking clad leg. His hand found it way up to the top of my stockings were I starting spreading my legs apart for him. Megan began kissing me as Robert moved up further to my crotch. He let out a little "oh" as his had found my hard cock and held it. He bent down and raised my dress with the other hand and in one motion pulled my panties to the side then replaced his hand with his mouth. Megan got up off the couch and disappeared. Robert got up himself and removed his pants. He dropped them to the ground and stepped in between my legs to which I reach for his underwear and helped him remove them. I gripped the ridged cock that pointed straight at my face. Just like I had always been doing this with Megan's fake cock I guided it to my waiting mouth. I took his cock in my mouth as far as it would go and let it slid back out with a popping sound. I engulfed it again bobbing my head on it trying to make it cum quickly as I really truly wanted his seed. In the mean time Megan had returned in nothing but her garter belt, stockings, and heels but now with the strap-on placed around her hips. I let go of Roberts cock and instinctively got on all four on the couch. Robert sat back on the couch at my head and Megan got in behind me. I waited as Megan lubed and inserted her phallic cock in me before I leaned down to begin sucking Robert off. I loved the feel of Robert silky smooth cock against my tongue as I licked the underside of it. I enjoyed the familiar taste of his pre cum as I licked it from the opening of his penis head. Megan was fucking me to her own rhythm because now I found my new love of sucking real cocks. I began to really go down on Robert trying my best to get his cock to shot his seed in my mouth. My work had paid off as he shot his load deep down my throat. I worked on him until he was dry. Megan could hear his moans as she really starting pounding deep in me bringing herself to a orgasm. After they both came I just got up adjusted my dress and sat back down between them both.
As Robert and Megan recovered themselves I suggest that we should have another drink. Megan was beside her self saying how good I looked with another man's cock in my mouth. I told her I couldn't believe how much I enjoyed, and in the still horny state that I was in announced I could blow five guys of in a row right now. She herself announced that it could be arranged. As we finished our drinks Megan asked Robert if he would like to take his turn fucking me, Robert eagerly agreed. Megan got up off the couch and had me lay on my back while Robert got in between my legs and grabbed my ankles pulling them up in the air and pushing my knees to my chest. My wife helped by pulling my dress up around my waist and removing my shoes, so I wouldn't put an eye out with the spiky heels. It felt wonderful as Robert moved my panties to the side and pressed his hard cock against my hole. He waited as I began to relax and open up to receive his cock in my ass. He slowly slid it in deeper and pulled slowly back waiting for me to loosen up for a good hard fucking. He moved his hip back and forth every so slightly increasing in depth and speed as he went on. I was taking his tool like a pro now moving with him. Megan would lean in a kiss me and talk dirty to me. I could almost cum just from the anal sex I was receiving. Robert was bucking away fucking hard while moaning and I could see him making faces ready to cum. With a grunt he stabbed deep into me, I swear I could feel his cum filling me up, he grunted and came, and grunted and came, filling me with his seed. I was lost in the feeling of just being fucked when at sometime Robert pulled out. I could feel the both of them pulling me farther toward the middle of the couch. When I opened my eyes Robert was placing a hand under my back and grabbed both ankles, guiding my feet up over my head. All I could see now was my own cock staring me in the face with my panties to one side. Megan reaches in and grabs my cock with her hand and starts stroking me. Robert now at my head, both of my nylon encased ankles in his hands, keeping my cock steady above my face. Megan then tells me that when I am ready to cum I am to open my mouth wide. She's jerking away and I felt my self ready to cum, I do as she asked and open my mouth. Then streams of my own jis shoot into my waiting mouth I swallow all that makes it into my mouth as more shoot on to my face. I can hear Robert gasp an "oh yes" as he then brings my legs back up. The both help clean me off with their tongues as I lay there thinking to myself, I want more as the sexual experience comes to an end.
On Saturday we again meet up with Robert. He had come over to our house to convince me that I do pass as a women and should go out to a club that caters to transgender people. After some doing Robert and my wife convince me to go out to the club that night dressed as Natalie. Megan and myself get dressed for a night on the town and I start feeling better about it. Megan and I meet Robert at he club, and they were both right, know one seems to care that I am a man in a dress. In fact when Megan left the table to use the ladies room I was approach by a married man looking to buy me a drink. The night went on I started dancing with Megan then Robert, and after dancing with Robert I was asked to dance by several men. My wife convinced me to go ahead and dance with them, so I did. I was told by two of the three guys how hot I looked and that they new my true nature. These guys were also married and told me about how they don't get blow jobs from their wives anymore. They kept hinting for me to meet them in the restroom to take care of them. I told Robert and Megan about this and they said I should go for it. I decided to give it try and got up and motioned for the first guy to follow me. I pretended to be washing my hands as he came into the restroom. He walked to a stall and held the door as I slid in with him. I squatted before him and helped him undo his trouser and proceed to give him a blow job right there. When he came in my mouth he thanked me and left. When I came back out into the club he was gone. The next guy I danced with asked me to dance again, while we were dancing he said he saw me go in the restroom with the last guy and wanted to know if I could do the same thing for him. I told go on I would meet him in there. I stopped by our table and told Megan what I was going to do and she gave me her approval. As I entered the restroom to my surprise I found Robert on his knees giving a young man a blow job. My gentleman was standing there watching, so I grabbed him by the hand walked him right next to Robert and his man then proceed to give him a blow job side by side with Robert. As Robert finished and his date left he watched me finish off my guy and stuck his cock in my face. While I was blowing Robert another gentleman had entered and was watching us with his cock out stoking it. Robert shot his load down my throat and I stood up looked at the man watching us and walked over to him. When I got right in front of him I asked him if he needed help and he nodded yes, so again I hiked my dress up a bit and squatted down to suck him off. Soon after that me and Robert went back to the table and told Megan all that happened she smiled and said what a couple of good cocksuckers we had been. That night when Megan and I got home she pretended to be upset about the blow jobs I gave and punished me severely for it. She then fucked my ass and we had the best love making we had in a long time.
The weekend ended and Monday I went back to being my wife's maid. I would clean the house and make myself pretty for my wife before she came home, but every day she would find something wrong just so she could punish me. Saturday came it was the night for the Halloween party. All day Megan and I prepared ourselves for the party. We bathed and shaved did our nails and make up. Megan helped me with my make up; doing a great job of making look like a young girl. She then helped me get dressed as Dorothy. I wore a pink and white satin corset with garter straps under my dress. Attached to the straps I wore a pair of shear nude color stockings over those I put on white nylon anklets with ruffled tops. I found the smallest pair of pink nylon panties that just barely covered everything. The dress was very short and slutty, it had white puffy short sleeves, the white and blue checkered dress was low cut showing cleavage, it had just enough crinoline to make the bottom flow out, and was so short the whole stocking tops showed. Megan was just beside herself seeing dressed as I was as she stood right in front of me and could not take her eyes off of me. While she stood in front of me staring into my eyes she pushed me flat on my back into the bed. Megan then jumped on top of me straddling my hips she then reaches back lifts the dress and pulls my cock out. She lowers herself on to my cock and fucks me like a cowgirl. She knows I now cannot cum unless she shoves something into my ass. I beg her to fuck my ass so I can cum but refuses saying that I would make a mess of my costume. After she had pleasured her self on me she asked that I leave the bedroom while she gets dressed. Megan told me she wants her costume to be a surprise. After about want seams like an hour Megan comes out of the bedroom dressed like a dominatrix. Not just a plain dominatrix she was dressed like Betty Page. Her outfit was a black pencil skirt, leather waist cincher, white blouse, black hose, and thigh high stiletto boots that had a holster for a riding crop that sat in it.
We were now dressed and headed out on our way to the party. When we arrived at the house for the Halloween party I had reservations about going in. I was afraid that I would stick out being a man dressed as I was, but when we entered the first couple we seen was a man dressed as Marie Antoinette and a women dressed as King Louis. I began to feel much better. During the party my wife and I had got many compliments on our costumes, the wives were really astounded that I was a man while their husbands drooled at the site of Megan and me. Megan left me at one point to talk to her boss leaving with Robert who had just showed up at the party with his date. She spent quite a bit of time talking to him. When she returned she took me to the side and said she had something she wanted to talk to me about. When we drifted away from everyone else she told me what her boss had asked her. He wanted to know if she would be willing to let him use me for an hour or two tonight. Megan explained to me that she told him all about me and that he himself was into transvestites and S&M. He wanted to have me tonight and was even willing to even pay me for sexual favors. My wife had brought up to me, even before I could answer, since I did not have a job and we needed the cash I should consider it. He even told her she could keep close by to make sure that nothing bad could happen to me. I thought about what she said and decided I would do it if she was in agreement with it herself. She kissed and we walked over to her boss to tell him our decision.
When we meet up with him Megan introduced me to him as Natalie, and with that he grabbed my hand a kissed the back of it. He was tall, well keep, and physically fit gentlemen dressed as a priest. Megan introduced him to me as Andrew; she then told him our decision. I could see the pleasured look on his face as our answer soaked in. Andrew was kind enough to ask me if this was going to be alright with me and said he was going to give us money and we were not going to refuse it. He talked to us some more about himself and how wonderful it was to work with my wife. He even wanted to know more about how I became this way, so I explained the whole story to him. As I was telling him about everything from my childhood till now, I could tell he was getting quite aroused. It was getting close to eleven o'clock and people we starting to leave, so he told Megan and myself to go up stairs and wait in the master bedroom as he saw the rest of the guest out. After about a half hour he joined us there.
He entered the bedroom smiling, we had more small talk about the party and discussed about the people that were there. Andrew again politely asked me if I was ready to get down to business and in so much told Megan she could wait in the room across the hall. Megan got up and kissed me as she then left the room. As soon as she left the room his personality changed. He began by telling me to stand forth at the foot of his large four poster bed. I did as I was told. I was made to stand there arms in front, hands clasped together, and to look at the floor. He removed his shirt and threw it to a chair. Without looking up I could see a wash board stomach and strong forearms as he walked around me looking me over. Andrew wanted to know why such a pretty girl as me would blow four strange guys off in a public men's restroom. When I open my mouth to answer he grabbed my chin and looked me in the eye telling never speak unless I was directly asked to speak. Andrew announced that type of behavior could not be tolerated and I was to be well disciplined for it. With that he walked over to what I thought was a closet door and opened it. He stood there holding the door for me and told me to step inside and stand over by the bench.
I did as I was told and headed for the bench. The room was looked like a den, wood panels for wall, deep red carpeting and no windows. Looking around the room I could see many things that were used for disciplining bad girls. Hung on the walls were whips, paddles, straps, dildos, and in a basket assorted canes. Besides the bench that I stood next to there was a large desk, a padded horse, and a cross in the shape of an X shape. Andrew walked up behind me and asked me to remove my panties if I had any on. I did as I was told and reach up under my Dorothy costume detached the garters so I could remove them. Replaced the garter straps to the stockings then waited. I was told to lay face down on the bench which resembled a stick figure that rose just a few feet above the floor. After I had laid face down on the bench he raised and adjusted my dress, I could feel the cool air on my bare ass as he pushed it up around my waist. With my feet hanging over the ends of the stick figure shaped bench he started strapping my legs down around the ankles to it. Then more straps held me down around my thighs, around my waist, and finally around my extended arms. Andrew asked politely if I was comfortable in which I just nodded my head yes, I was complimented that I was a good girl, because I knew not to speak. I could see him walk away towards the wall where all of the nasty looking spanking implements were. He had chosen a thick two foot long strap from the wall and came back standing next to me. He explained I was going to be punished until he decided when I had enough. I felt him then place the strap across my backside lining it up. Now with him standing he could bring down and place very hard strokes across my bare ass. The large strap was removed and brought down hard across both ass checks hard. I let out a small "awh" as I struggled against my bonds. Again he struck me hard with the same results. I was given a total of thirty strokes before he released me from my bonds. I was told to get up and go look in the mirror to see what he had done to me. I did not really have to look I could fell the warmth rising from my well strapped ass when I place a hand to it. He was not done yet as I could tell because he placed the strap back on the wall and replace it with a paddle. I was lead to the large desk told to bend over it and place my arms upon it. Standing behind me he tapped the inside of my legs wanting to spread them a little farther apart. I did as the paddle directed me to. I felt him place the paddle against my ass lining it up and pulled it back, it then stuck me making me rock forward toward the desk. Andrew waited as I realigned myself before paddling me again. He would wait each time for me either to regain my composer or to get back into position after each swat. This went on for fifty strokes. I was rock hard and my knees were knocking for the last ten swats that I had received. I was told again to go look at his work in the mirror and could now see a bright red a slightly bruise bottom.
Andrew the picked up my panties and tossed them to me. I did not put them back on as I knew better. He then went back to the door and held it for me as he motioned with one hand for me to return to the bed room. I had wished I could have put them back on because with each step the material from my dress felt like it was like sandpaper being dragged across my ass. I was directed toward the foot of the four poster bed and made to stand facing it. I had not noticed before that on each of the seven foot tall posts a silk rope hung there. Andrew standing behind me helped me remove my dress. As I stood there just in my gartered corset stockings, anklets, heels he lifted each arm and tied them to the bed posts. He then bent down to tie each leg, feeling each one of the nylon encase leg as he tied them to the bottom of each post. He left me tied standing spread eagle to the bed and left the room. When he returned he had Megan's riding crop in his hand. With out warning or lining up he whipped each upper thigh five times each. I struggled at the ropes feeling the welt that were most likely left there by the crop. He took turns striking each buttock that seemed like forever. When he had finished he threw the crop to the bed and starting touching his work that he left on my backside. Satisfied with his work he placed a lubed finger to my pussy hole. I felt his long finger probing me deeply. As soon as his finger was removed I could hear him undoing his belt and trousers. I then felt his arms around me and his hard cock pressed against my back. He then removed one arm so he could guide his cock into my ass. I felt the stiff member push against my hole, then he raise up against me shoving it in. I felt pain from him entering me so fast then suddenly pleasure when he stopped and was fully inserted inside me. He hammered away inside me forcefully as he dropped a hand to my cock just holding it not stroking. He then stopped fucking me but stayed inside me as he untied my hands, I fell to the bed where he pulled out. Andrew directed me to untie my feet in which I did with trembling hands. He the grab me and turned me around, placing his hands on my shoulders he pushed me down to my knees. I could now see he large cock at least nine inches long. He placed a hand against the back of my head and shoved the cock into my mouth. Grabbing the side of my head he fucked my mouth. I could feel his cock pulsing in my mouth then all of a sudden he pulled it out and stroked it in front of my face. I instinctively opened my mouth and stuck out my tongue. He masturbated himself until he shot his load all over my face and into my mouth. Andrew then lifted me up and sat me on the bed and proceeded to give me a blow job. My wife must have told him about how I needed something in my ass to make me cum, because when he rammed a finger inside it I came as soon as his knuckle slid passed my opening. Andrew invited Megan and me to stay the night, but she politely refused. We said our good-bye's and headed for home.
The next morning I awoke still sore from last night. Megan was quite please with me as I had earned some money. The rest of the day she let me recuperate from the night before. Monday came and I resumed my position as the house maid. Megan returned home that evening and said she had good news. She told me about Andrew was giving her a promotion to a position in the corporate office and I had also had a job working for Andrew. My wife explained the job I was going to take was going to be the same thing I was doing for her at home. Before I could protest I was told I would not be allowed to turn it down, since I could not find work this was what I was going to be doing. I was to start this Wednesday from ten o'clock in the morning till two o'clock in the afternoon, as this was the day Andrew always took off. She said they reached this agreement so I could be at home when she got off work. They had also agreed on payment for my services. I did not really find this to be a bad offer but try to look discussed, besides I had really enjoyed what happened that night with Andrew and could not stop thinking about it. Wednesday came and I went to Andrew's house, arrived ten o'clock sharp. The day was as I expected dressed in my maid outfit, me being punished for not working to his standards, and him using me for his sexual pleasures. When my day ended that afternoon I was asked by Andrew if I could be his date for Friday night for dinner. If I was willing he said for me to clear it with my wife and tell her I was going to be paid for the evening. Right there I new I was becoming a lady of the evening as Megan would most likely not let me turn it down. That Friday I went on my date with Andrew all went well as he treated me as a lady. After dinner all I had to do was blow him in the restaurants parking lot before he took me back home.
Saturday the day after my date with Andrew my wife had received a call from him. She talked to him for awhile on the phone. When she was done I quizzed her about what she and Andrew had talked about, because most likely it was about me. Megan then told me about the conversation. It was about how much he enjoyed the date and that I had passed. I wanted to know what she meant by me passing. It was explained that I would make the perfect girl to entertain clients for Andrew. Megan also flat out told me that she thought I would never go back to being full time man and it seemed that I really enjoyed being a call girl. I told Megan I had to agree with her I did not want to give up living as a women and enjoyed having sex like one. The best part I was being paid for what I loved doing. With that she told me to we better get busy as I had a job to get to that evening.
My first job as a transvestite call girl I was to meet this client at his hotel room. I was to be dressed as a bride for him and the rest of the details would be disclosed if he liked me. Megan and I had to do some shopping as I did not own a bridle gown. We went to a shop near the mall that was loaded wall to wall with new and used bridle gowns. An older lady was talking to Megan the whole time as we decided which ones to try on. When we had picked out several that were in my size we asked where we might try these on. The women told my wife we could use the dressing room over toward the back and lead us toward it. The women waited as I went in and tried the first one on. When I came back out she had me stand on dais at checked the fit. The women then said something that neither of us expected to heard. She wanted to know if Megan's boyfriend (me) wanted to gather the material in the back of the dress to make it fuller. My wife laughs and asked her how she knew. She said she get many transgender people in here wanting to play the bride. We enjoyed the older women the whole time we were there. We had picked out a full length gown with long sleeves. We also purchased a veil and shoes to go with the gown, paid and left, not before thanking the women for all her help and understanding.
We went home to get me ready for my date. I was beside myself while dressing as a bride. I could not believe how exciding it I was that I was going to be a bride. We picked out a pair of white satin panties with a shear back. I put on my white six strap satin garter belt. Slipped white seamed stockings on my legs and wore a white long line bra. For the trip over to the hotel I wore my blue polka dot dress and navy blue open toe pumps. Megan dropped me off at the hotel and I proceed to the lobby phone with the wedding dress, veil, and shoes in a bag over my shoulder. I called the gentleman that I was going to meet; he sounded very excited when he invited me up to his room. I stood nervous in front of his door and knocked. I was met at the door by and older gentleman who said his name was Jack as he looked me up and down approving. He invited me in were I asked where can I change. He point to the bathroom in which I proceeded to and entered. After changing I came back out into the hotel room to find him sitting on the edge of the bed.
He then asked me if I wanted a drink to which I accepted his offer. He got up and poured two drinks and handed me one. We stood and talked, he couldn't believe I was a man and wanted to know more about me. When I had told him a little about myself he then asked if he could see my feet. I lifted the wedding gown and showed him my feet with my white strappy sandals, revealing my French style painted toes under the white stockings. He then asked if I could remove the shoes, so I sat on the bed and slowly raised a foot and asked him if he would like to help me remove them. He set his drink down and grabbed the back of my calf with one hand and placed the other at my heel. Jack then bent down and kissed my toes. He then undid the ankle strap and slid the shoe off. I pointed a toe out toward him in which he kissed it again and began to massage my foot. Jack repeated the same routine with the other foot. I then placed a shoeless stocking foot against his crotch and rubbed his cock that was still in his pants. I asked him to step forward so I could help him remove his pants. With his pants undone and around his ankles I began again to rub a foot against his now exposed cock. Seeing this was really turning him on, I slid back further onto the bed and put both feet up to his crotch. Jack then took both of my feet in each of his hands. He held them in place as he stuck his penis between the arches of my feet. He then fucked my feet as I held the balls and heels of my feet together making a tight vagina with them. He was getting no where fast fucking my feet so he let them go and started jacking off aiming his cock over them. I kept both of my toes point out just under his cock and not before to long he came on the tops on them. He pulled his pants back up and fastened them. Jack then wanted to know if I could jack off in front of him so he could watch. I of course said I would but mentioned that I need something in pussy hole or I could not cum. With that he gave me his hand and helped me up off the bed. I then pulled the front of the wedding gown up and started undoing the garter straps from my stockings. Jack then got down on his knees and helped me remove the hooks from the stocking, but not before feeling nylon material on my legs. When the strap hooks were undone I put one hand on Jack's shoulder as I removed my stockings from my legs. He wanted to know if he could keep them, in which I handed each one to him. Jack then handed one stocking back to me. He asked me to slip it over my cock and leave him my seed in it. While Jack was still on his knees he positioned himself behind me. I felt both his hands go up my gown as he raised the gown up around my lower back. He held it there with one hand as his other removed my panties. He held the panties as I step out of them. He then placed both his hands on my ass and spread them apart. He asked me to let him know when I was about to cum, as he wanted to see me shot my load. Jack then proceeded to place his ridged tongue against my rosebud. He flicked his tongue on the outside of my pussy hole before he pressed it into my hole. His rimming got my really hot to which I lifted the gown again to expose my cock to start jacking off. When I was close to cumming I reach back with one hand and place it on Jack's head letting him know I was ready. He dropped my dress and sat on the bed and watched me finish myself off into the stocking.
When I had finished with Jack I called my wife to tell her to come pick me up. I had dressed back into my blue with white polka dot dress, minus the stockings, and meet my wife in the parking lot. When I slid into the passenger seat we left for home just completing my first trick. On the way home my wife inquired what had happened to my stockings. I told her about the things me and Jack had done that evening. She was getting turned on by it and had announced that I would have to be disciplined for loosing my stockings. I was not upset that I was going to be punished in fact I was looking forward to it. Besides I love my new role in the relationship and would not change anything about it.
The months went by and I had turned many tricks with Megan's and Andrew's clients from the bank. I also pick up a few other's outside of Megan's work. As time went on Megan had quit her job at the bank and we started working for ourselves. She became a full time dominatrix and I was a she-male call girl. With the money we made I had gotten breast implants and let my hair grow long. We would from time to time work in tandem but mostly alone. Megan and I found it interesting that ninety percent of our cliental is made up of married men whom say they are straight. We also get some of our income from a web site we started by selling videos and doing live feeds. We hope to make enough money in the next ten years or so in order make just videos to sell on line, as we hope to stop turning tricks some day.
Thanks for reading I hope you enjoyed it I love writing them,
Natalie