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First Time SurpriseTammy and I were home alone on a lazy Saturday evening just sitting around the house. The boys were at their dads for the weekend and my daughter was at her mothers visiting for the weekend. It was early evening and as we sat around with nothing to do Tammy turned to me and said she had the perfect plan for the evening and for me to get up and dont ask any questions as she was in charge of the evening. She got up from the sofa and I obeyed and got up behind her and she said to follow her into the bedroom. I thought to myself this is going to be good because she is going to let me eat her pussy and fuck her until she squirts all over me because she knows that I love it and it always turns me on. Once we reached the bedroom she told me to strip and to head to the shower. I did as I was told and hurried to jump into the shower and Tammy was right behind me. As I adjusted the water to the right temperature I turned to her and said arent you going to get undressed and join me and she slapped my face and told me to shut up as she did not give me permission to speak to her. I turned red in the face but didnt say anything. That slap had me turned on and my cock jumped and got harder when she did that. I stepped into the shower and she told me to start shaving my body and she wanted all the hair gone. I looked at her and she looked directly back at me with those beautiful eyes but there was something different about them this time. It looked like she meant business so I didnt argue and I picked up the razor and the shaving cream that she had already put by the shower I guess earlier. I started to shave from my face and down to my arms and then under them. All the while she stood there and showed me a spot that I might have missed and told me to keep going. I then shaved my chest and all around my cock and balls and then started on my legs. I finally got finished shaving what I could reach and she then took the razor from me and shaved my back and ass and made sure there was no more hair on my body except for the little on my head. She then had me wash off and get out of the shower. When I was toweling off I noticed how different it felt to dry myself without any hair on my torso. It actually felt nice and my skin felt smooth. After I had finished drying off she told me to go into the bedroom. When I got there the first thing I noticed was a nice looking short black dress and some black crotchless pantyhose and a black thong and bra lying on the bed. I wondered to myself how did it get there because when I came into the bedroom earlier I didnt see it there. Tammy told me to go and put everything on and when I walked to the side of the bed where everything was there was a pair of 4 strappy toed shoes on the floor besides the bed. I was excited to say the least and wondered how could she have known my secret desire to dress as a pretty woman because I had told no one of this before. I tried to go slowly because I didnt want to rip those pantyhose as I was nervous about all of this. She told me to hurry up and get everything on because we she had plans for me this evening and she wanted to get them started. I hurried and put on everything and after I put on those heels I stood and wobbled some because I wasnt used to wearing high heels. I was excited though and then Tammy told me to come and sit by the kitchen table so I followed her into the kitchen and she had make up and lipstick sitting there along with a long haired wig. She first had me sit up straight in the chair by the table and put the wig onto my head and adjusted it and combed it out. Then she began to apply the make up onto my face and she did my cheeks then my eyes and made my lashes stand out long. She then had me purse my lips and put lipstick on me. Needless to say by this time my cock was ragging in those tiny thongs she had me put on and it was leaking pre-cum and had them soaked. After she finished applying my makeup she told me to sit there and wait for her.
I did as I was told even though it took all my strength to stay put because I wanted to see myself in the mirror to see what I looked like. After what seemed like an eternity which in reality was only about 15 or 20 minutes she came out of the bedroom looking as sexy as she always does in a short dress with pantyhose and heels on. I was staring at her and longing to hold her and kiss her with my lipsticked lips onto her lips which were also donned in lipstick. She told me to get up and follow her to the bathroom and took me in to look at myself in the mirror. What I saw was not Randy but a woman looking back at me. Now to say it I was a beautiful woman Im not saying that but she looked decent and was very prettily made up in her makeup. My cock was still straining against the tiny fabric which was holding it in and you could see it bulging in the front of the dress some. Tammy told me I better loose that erection because she was taking me out of the house and if I didnt want people staring at me I better will myself for it to go down. I then thought to myself that I had never dreamed of going out of privacy dressed like that and started getting scared. I wanted to protest to Tammy but I knew better if I didnt want another slap or even worse maybe a spanking with the leather paddle. She said lets go and told me to try to carry myself like a lady in public. We got into her car and she started it up and again I was still in disbelief that I was actually out of the privacy of my house looking the way I did. Tammy started driving towards the lake and then turned to go toward New Orleans. We road there in mostly silence and I was again scared to death and was hoping nothing happened to the car where we would be stranded on the side of the road and then I would be found out. We got to New Orleans and Tammy parked just outside of the French Quarter and said lets go and she opened the door for me to get out. When I slid out of the car she told me she could see my panties because the dress was so short. I turned red from embarrassment and she grabbed my arm and put hers into it and we walked like that down towards Bourbon Street. Once we got on Bourbon Street we made a few blocks and then she turned down one of the small streets and came up to a bar called Queenies. We walked in and once inside there were lots of people there and lots of women but something looked sort of strange about them. Then I figured it out that they were all women like me which were actually guys dressed as women. Some of them looked really HOT and some were just plain looking. Tammy found a spot at the bar and she and I took a seat and when I sat down I noticed my dress road up my thighs just below my panty line. I had to keep my legs crossed so no one would notice the bulge in my panties as I was so turned on by the good looking cross dressers in the bar. As we sat there Tammy ordered herself a drink and told me that I should get something to drink even though she knows I dont drink because I will be performing for her later with one of these women in here. I told her in that case I better get me something so she ordered me a vodka orange juice and I asked her to make it a double shot which she did after she giggled some. As we sat there one good looking cross dresser approached us and she asked if she could join us at the bar or if we cared to we could find a table away from the bar and sit and talk. Tammy told her lets find a table in the corner so that is what they did. I followed close behind them and when we got to the table Tammy had me sit and then the pretty cross dresser sit then she sat. The pretty cross dresser that joined us I found out was named Chrissy and she and Tammy had met before while I was away because Tammy had taken her shopping for her clothes. Then I figured it out that this was all planned by Tammy for me. I smiled at Tammy and mouthed the words to her that I LOVED HER and she knew why already. As we sat there and made small talk Tammy said she wanted me to kiss Chrissy while she watched because she thought that would be so HOT to watch so I hesitantly leaned over towards Chrissy and she leaned into me and we started kissing softly and then harder as we tasted each others lipstick. It really turned me on to do this as Tammy watched us and again my cock was getting harder than before and leaking like a faucet with pre-cum soaking my panties. I brought my hand down under the table and felt a cock for the first time in my hand that wasnt my own cock as we were kissing and then Chrissy did the same to me and it really felt good and almost a natural thing to do. Tammy then said for us to save it for later where we could be alone because she had plans for the two of us. We broke off our kiss but I kept my hand on Chrissys cock through her panties while we talked some more. After about an hour Tammy decided that it was time to leave and she told Chrissy to follow us home so we headed back across the lake to our house. Once we got there Tammy said that she would take control for the night over the both of us and whatever she wanted we were to do no questions asked or if not Chrissy would have to leave. Chrissy and I both agreed to her terms. Tammy said the first thing she wanted to do was to take pictures of the both of us dressed up so we stood side by side with our arms wrapped around each other and Tammy started taking pictures. She told us to kiss again while she took more pictures and had us put our hands under each others short dresses so she could take more. After a while Tammy said it was time to go to the bedroom and so we all headed that way. I did not know what Tammy had in mind but Im sure whatever it was I would be good with it as she wouldnt do anything to hurt me. When we got to the bedroom she said for the two of us to kneel with our asses in the air facing her where she pulled out the leather paddle and told us to raise our dresses out of the way so she could get at our asses. Tammy started with my ass first telling me that she has been waiting to spank me for a long time and she then raised the leather paddle and started spanking my near naked ass through my pantyhose. It stung me at first and it hurt some but Tammy said not to move and to take it. I obeyed even though it was hurting me but as she kept on going a strange thing happened and it actually started feeling better and the pain was going away and my cock was throbbing like never before. She kept it up for a few more minutes and then suddenly as fast as it started it stopped and I was almost to the point of begging for more. Tammy got the camera out and took pictures of my red ass for her to look at later. Tammy then started spanking Chrissys ass and gave her about the same amount and stopped and also took pictures of her red ass. After Tammy said that she wanted us to kiss again and to feel each other up while she took more pictures and after a while made us turn around to get into a 69 position. This was my first time being this close to another mans cock so close almost touching it with my face, Tammy told us to pull each others cock out and start licking and sucking each other and she took more pictures of us doing this. After not too long of a time period I felt Chrissys cock start to swell and his breathing started getting shallow and mine also felt like it was going to explode in his mouth anytime soon. Tammy told us to go ahead and suck each other off and to swallow each others cum while she took more pictures but we were to keep in mind that we werent finished yet so we better be able to get hard again later because she had more planed for us. I felt Chrissys cock twitch and felt the first load of cum hit the back of my throat and I swallowed it all up but then came more spurts of cum and it felt like it would never stop and the whole time my cock was squirting in his mouth too. I found out that I loved the taste of cum and sucked him until all of it was in my mouth and swallowed it all down my throat. I licked his cock like an ice cream cone to clean off all of his cum as he did this to mine. After we did this Tammy said for us to touch up our makeup and lipstick while she got ready to join us in bed. When we finished with this Tammy told us to lie on either side of her and she wanted for us to suck her tits and work our way down her body to her sweet pussy and wanted us to make her squirt. Both Chrissy and I did as we were told and when we got to her pussy our mouths met there and we kissed her pussy together Tammy began to squirm and then she lost control and squirted her pussy juice across both of our faces. She squirted so much that between the both of us we couldnt drink it all so the bed became soaking wet with her juices. Chrissy was so impressed about her squirting that he just sat back and watched as I tried to lick her clean. After Tammy got off for the first time I got up and went to get the towels and place under her on the bed. After she repositioned herself on the towels she said that she wanted us to fuck her good, one is her pussy and one in her ass. She told Chrissy that her ass was only mine and that no other man would be allowed in there that it was reserved only for my cock. She moved aside and I laid besides her and Tammy got up and then squatted down over my cock and sat on it all the while moaning in pleasure. After she was comfortable with my cock in her ass she told Chrissy to get behind her and for her to fuck her pussy. Chrissy got into place and Tammy stopped rocking on my cock long enough for Chrissy to stick her hard cock into her pussy and as soon as Tammy felt it going in she let out a moan of pleasure. I knew Tammys dream was to have two cocks in her at once so I know she would enjoy this very much and I couldnt wait for her to cum again while riding my cock with that tight ass of hers and then feeling her cumming and wetting me when she did. This always was a turn on for me to feel her squirt all over my cock and balls. Tammy started rocking back and forth slowly getting used to the two cocks in her and when she got used to it she started moaning and moving faster and faster until she started screaming my name and telling me how much she Loved me and that she was so happy that I could share this with her. Tammy then started squirting again on Chrissys cock and balls and then it was running down between her and I and I could feel it also over my cock and balls. Tammy finally stopped exhausted and laid down on top of me with both of our cocks still in her and then started kissing me and telling me how much she Loved me. Tammy then told Chrissy to remove her cock out of her because she wasnt finished with us yet. As Chrissy moved from her pussy Tammy raised up and my cock popped out of her ass and she moved off of the bed and told me to stay where I was. Tammy told Chrissy to get on top of me and to straddle my chest so I could lick and suck her cock. I have to say that the idea was exciting. Chrissy placed her cock against my lips and Tammy told me to open up and take her into my mouth. When I opened up Chrissy began shoving her hard cock into my mouth and the first thing I thought of is how good it tasted. As a matter of fact I could taste Tammys sweet pussy on it. Chrissy began to shove more and more into my mouth and it felt so good and natural to me and I wanted for Chrissy to cum in my mouth again but as Chrissy breathing was starting to get shorter and shorter Tammy told him to stop because she wanted to use that cock for another purpose. Tammy was taking lots of pictures the whole time of me sucking my first cock for the second time tonight . Tammy told me to get up and told Chrissy to lie down on her back which she did and her hard cock was sticking straight up into the air. Tammy got the lube and told me that I was going to take that huge cock up my virgin asshole so get ready for it. Again I got nervous and thought what if I couldnt handle that cock in my virgin ass but Tammy told me to relax and she lubed up my asshole and his cock then helped me sit over him and guided his hard cock into my asshole. I started going slowly down on it and my ass was eagerly sucking it in and I couldnt believe that it felt so good. The whole time Tammy was by my side holding my hand and smiling at me and telling me how much she Loved me and what a turn on to see her man looking so beautifully dressed as a woman taking his first cock in his virgin asshole. She then kissed me deeply and told me again how much she Loved me. As I lowered myself down and took more and more of that hard cock in me I began to enjoy it so much that I started taking him all the way down to his pelvis and grinding it into my asshole. I then started riding him faster and faster all the while Tammy was recording this for our viewing pleasure later on to turn us on again and again. Chrissy also loved being in my virgin ass and told me she was going to cum it felt so good and tight so I told her to go ahead and cum in my ass and then I felt her cock swell even more then release a huge load of cum into me. I kept riding her until she told me to stop because she got too sensitive. I sat there for a few more moments feeling how great her cock felt in my ass and then I got off of her and was disappointed when it finally popped out of my ass. My ass seemed to have a mind of its own and wanted more cock but I knew Chrissy was spent so it wouldnt happen again for a while. Tammy saw that I was disappointed so she hurriedly put on the strap on and laid down and told me to sit on her fat cock. I jumped at the chance and sat my cum filled ass onto her fake fat cock and took the whole thing down in one smooth motion. It felt so good that I never wanted to stop and so I started rising up and down on it faster and faster and Tammy was also feeling the base against her clit so she was getting excited also. I motioned for Chrissy to come over and she knelt down between Tammys head and me and her cock was coming back to life so I took it into my mouth while Tammy watched then Tammy raised up some and she started licking one side while I did the other. Chrissys cock started growing to its full length and getting hard again. Tammy and I both worked on it and after about 10 minutes of us both licking it Tammy put in my mouth and told me to suck as much of him as I could down my throat while she watched. I got most of him in my mouth and started sucking it up and down faster and faster and then she announced she was going to cum again so Tammy said she wanted to share it with me. I took his cock and placed it between both of our lips and when it shot off it landed on our lips and we both began to lick each others face and lips and swallow his load. We then kissed deeply and tasted his cum in both of our mouths. My cock was starting to swell so I told Tammy I was going to cum so she grabbed Chrissy by the back of her head and put my cock in her mouth just in time for my cum to fill her mouth. Chrissy couldnt contain such a big load and had some of it leaked from the corners of her mouth so she bent down and both Tammy and I licked my cum off of her face and then Chrissy turned and kissed me with more of my cum in her mouth and fed it to me to swallow. It was the hottest sex Tammy and I have ever experienced and when we were through and Chrissy left Tammy told me I had one more task to do before I got undressed and that was to lick her pussy until she squirted into my mouth which I gladly did. After she came and squirted her juices in my mouth we kissed and then got up to take a shower together. Tammy then pulled out a beautiful negligee and a pair of lace panties and told me to put them on and then she dressed the same and we crawled in bed together and hugged each other and feel asleep in each others arms. As I was falling asleep my thoughts were nothing but the LOVE I have for Tammy and her understanding and hopefully she enjoyed it as much as I did and if she did then we could do this again sometimes which would make my life complete being with the one I LOVE and her understanding my kinky desires
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