Tranny Stories |
John and I were having a nice relaxing afternoon cuddled up on the couch watching TV. Our relationship was shifting from all about great sex to enjoying the time we spent together just being ourselves, with me dressed up of course, and the sex seemed to me to be more loving. I'd still seduced him at times but most of our sex would just begin with us playing around. More like couple sex. But we still had our hot moments. After 3 months I've still yet to ever be in John's house without being Cheryl. That's how I liked it.
While we were talking that day John mentioned his friend Doug, who he had mentioned several times before and how he was planning to go visit him and how he'd like to take me along. I was in shock. In surprise I asked John, "Does Doug know about me?" Whenever Doug was mentioned it was mostly about John's business dealings, I hadn't known them to be good friends, especially when it came to knowing about me. John told me Doug knows. I asked John to fill me in.
They met several years ago in a m4m chat room, both were tops looking for bottoms. They chatted a lot, had the same interests, worked in the same field and became fast friends. They met each other several times for guys weekends and from their friendship came some business opportunities that worked out well for both of them. It was purely non-sexual and they stayed in touch often. During one such time Doug had asked if John had meet anyone special and John told Doug about me. He promised me he didn't give too much detail other then at how happy he was. That made me feel good.
So I asked why would he want Doug to meet Cheryl? John told me that if we were ever going to have a threesome, he'd want Doug to be the third because he knew he was a very good guy, was safe and most importantly discreet. It had been a few weeks since John had bought up the threesome topic so I thought he may have forgotten about it. I didn't tell John, but I did on a couple occasions jerk off while thinking about it, but I thought if I told him he would push for it. As excited and into it I was, I didn't want to let on. So I asked that if that ever did happen, to tell me about Doug. John told me Doug was a few years older then him, over 6' tall and about the same body size and weight as him. He never saw him naked so he couldn't tell me about that part. I told John I would hope to always be with him and that it didn't really matter. I didn't even ask to see a picture.
John then asked me if I would be willing to go to Pennsylvania with him next weekend. This was a huge step, I started asking questions but John said he had everything planned out for me not to worry. We'd travel down Friday just for the night, he got a 2 bedroom suite since we've never actually 'slept' together and I would have a room to change in in private and Doug would never see me as me, just Cheryl. I asked him if he was 110% positive that he really wanted to share me in a threesome to which he said 90% sure. I trusted John so I said OK.
We arrived at the hotel at 6:30, it was less then 75 minutes away from home so the anxiety wasn't too bad to handle. As soon as we got to our room I at John's suggestion went to get dressed comfortably sexy, he suggested lingerie. Doug was arriving at 7:30 and John was putting the 6 bottles of wine on ice. I took a quick shower and started to get ready for I didn't have much time. Applying make-up still took me a while. I had my outfit picked out. My fav 4” black high heels with ankle straps, black thigh highs and g-string. I also had matching black satin chemise and long black satin robe. I put on my brunette wig, hoop earrings and fake diamond necklace. I went a little darker with the make-up, a deep dark purple lip stick and eye shadow. I wanted to look mature and sexy.
Before I was finished I heard Doug arrive, he and John were talking and suddenly I started to get a bulge. I took a minute to relax since all that was left was to walk out there and I wanted to compose myself. I've been practicing my walk and voice for weeks and wanted them both to be perfect. I practiced both while looking into the mirror and when I had them down I decided it was time to enter the living room.
As I walked out my room John said "Hey, beautiful" and introduced me to Doug. OMG, he was gorgeous. He had that sexy manly mature look that made girls wet or in my case, my ass relaxed to be entered. We kissed each other on the cheek, with me in heels we were the same height, and I said I was pleased to met him, John has mentioned him numerous times. He told me I looked stunning. John suggested we sit down and have some wine. As John handed me my first glass he whispered in my ear how my voice turned him on. John was so special making me always feel good.
John was the perfect gentleman filling everyone's glass the whole evening. I think he wanted us all to get drunk to get things rolling. We had a very pleasant conversation and after the 2nd bottle the conversation started to get a little more risqué. John was sitting next to me rubbing my crossed legs softly and I saw Doug several times checking out where John's hands were as well as my legs so I started rocking my foot back and fourth to get more of his attention hoping that might be getting him horny. I was getting horny myself just thinking about what was going to happen so I placed my arm under John's and started rubbing the inside of his thigh. John started to bulge slightly and after he paid me a compliment to Doug I asked him to look at me and planted a soft tender kiss on his lips. I felt his bulge hit my arm so I knew it had worked.
Doug commented on how good we look together and I said, yes, there are many things that we were good together at especially the hot sex. I could tell they both couldn't believe I just came out and said that but I felt the need to get things going myself. John thanked me and started kissing me. We were making out and softly caressing each other. After a minute John pulled away to comment how it is rude to leave out our guest and asked if we should go into his room. Doug said that was a good idea and he'd bring in a bottle of wine. John held my hand as he lead me into his bedroom. His palm was sweaty so I knew he was a little nervous. I walked in and put down my glass as John suggested that maybe Doug and I should get to know each other a lil better. I turned to face both men and slowly untied my robe and pulled it so it would fall to the ground.
Doug said wow. I walked up to Doug and we started making out. He had his hands on my ass in seconds and was rubbing and grabbing my ass cheeks. It was hot. I looked at John and he was busy putting lube and condoms out. Watching us kiss must have got him all horned up. I kissed Doug again and he pulled me closer. I felt a huge bulge in his jeans and felt the need to investigate. I slowly dropped to my knees, unzipped him and pulled it out. OMG, it was at least an inch and a half longer then John's, and a lil wider. I licked the tip and as I started taking it into my mouth slowly started stroking it. It was delicious. It was so big I started gagging a little while trying to take more of it in. John asked me if I liked it and I told him yes.
I told Doug to lay back on the bed and quickly turned to John who was standing naked next to me and took him into my mouth. He was as hard as I had ever felt him so I didn't suck him too long. I knew he was going to cum quick in all this excitement and wanted him in my ass most of that time. I moved up onto the bed and got back to working on Doug's big cock. I left my ass hanging at the beds edge so John could fuck me from behind. John gently pulled aside my g-string as he entered my man pussy slowly. Between that and having Doug in my mouth I myself was in heaven and hard as hell.
Doug placed a hand on my head to lightly control the motion of me sucking on him. Doug and John were both moaning as I tried to get as much saliva on Doug's cock to make it as wet and warm as possible as I was quickly sucking him. His size let me use my hand to stroke him at the same time. I was impressed by John as he took his time on my ass with nice long slow strokes. It felt wonderful. I knew if I moaned John would shoot but I couldn't control myself in all the excitement and took my mouth off Doug's cock briefly to only ask John to “Fuck me baby, keep fucking me” in a mild girlish tone. As if on queue John started grunting as he pumped me a few times harder and let us know he was cumming. The rock hard cock in my ass felt awesome while I continued to work on Doug with my hand and mouth. John pulled out of me, yanked off the condom and shot all over my ass. I felt his warm sperm being rubbed in my ass by his softening cock.
I looked at Doug and asked him if it was time to put on a condom. He said it was. As Doug put on a condom I moved myself up on the bed to lay next to him. John commented at how great that felt while watching me suck Doug with a big smile on his face. Doug was quickly ready as he positioned me onto my back and himself between my legs. He raised my ankles upon his shoulders and took off my g-string which now exposed my opened my ass and after John handed him lube which he squirted some on both my ass and his cock, he guided his large cock to my gaped ass. He entered me slowly and asked if I was ok as I grimaced a lil bit. I told him it was fine and to enjoy me. Doug started slowly and after all seemed good he quickened his pace.
John stood a few feet away from the bed lightly stroking his cock and said “Cheryl, you look so beautiful right now”. I smiled at John while enjoying Doug's large cock working my ass. I reached out to grab John's cock and pulled it to me to put in my mouth. His semi erect cock felt good in my mouth as Doug kept pumping away. He let go of my legs so I wrapped them around him to keep him close. Doug started grunting a lil louder and I asked him to cum on me when he felt the urge. He kept pumping away for several minutes. I continued to suck John's now hardening cock. Doug looked into my eyes as I was starring directly into his as I played with John's cock with my mouth. I knew that excited him as he pumped me harder and harder the more he watched. Shortly after his fastest pumps he pulled out and ripped off his condom. I let John's cock out of my mouth as I begged Doug to cover me with his cum and he did. I quickly felt a large warm load covering me as I reached down to rub it in while saying “Yes baby, that's it, get it all out”. All the while Doug and my eyes were locked together.
Before I could even enjoy this very intense moment being shared between Doug and I, John reached out and pulled my head towards his cock and he was stroking himself to another orgasm. I opened my mouth as John grunted and I felt a trickle hit my face. It was a small load but the look on John's face told me it was a powerful one. I took him into my mouth to gently coax him while he softened in my mouth. He said "holy shit" as he was regaining his composure. John has never cum twice that quickly before while with me alone so I knew that this experience had have excited him beyond belief.
The three of us laid on the bed together and had several soft kisses. All mentioning how great it was. John then went down on me to reward me for the great time we just had. As John was sucking me off I looked up at Doug as we again locked eyes together. He reached out and held my face so gently. Doug and I seemed to quickly develop this unmentionable deep desiring lust for each other. I would just melt looking into his eyes. He leaned over and we started making out. I was so excited by Doug that I quickly began gyrating my hips as John was sucking me and I cried out “Oh yes” as I shot my load into John's loving warm mouth. In seconds I felt so guilty because it was the Doug I was thinking about as I came. I closed my eyes and let my head hit the pillow as I just laid and relaxed.
After a while Doug said he'd better take off, he had a busy day ahead as we were all getting out of bed. I mentioned how I was exhausted, worn out and a lil sore and needed to go get some sleep. I told Doug it was a pleasure meeting him again as I kissed him softly good night. I then walked over to John and tenderly kissed him good night. I picked up my robe and asked John what time we were leaving the next day. He said 10 so I told him I'd see him then. I told the guys to have fun and headed off to my room.
As soon as I got there, I took off my heels and wig and went straight under the covers. I started to go over everything that happened that night in my mind. I felt so guilty but didn't let that bother me ask I jerked off thinking about Doug one last time that evening. My orgasm felt great as I shot it out on my groin and then just closed my eyes and fell fast asleep.
While we were talking that day John mentioned his friend Doug, who he had mentioned several times before and how he was planning to go visit him and how he'd like to take me along. I was in shock. In surprise I asked John, "Does Doug know about me?" Whenever Doug was mentioned it was mostly about John's business dealings, I hadn't known them to be good friends, especially when it came to knowing about me. John told me Doug knows. I asked John to fill me in.
They met several years ago in a m4m chat room, both were tops looking for bottoms. They chatted a lot, had the same interests, worked in the same field and became fast friends. They met each other several times for guys weekends and from their friendship came some business opportunities that worked out well for both of them. It was purely non-sexual and they stayed in touch often. During one such time Doug had asked if John had meet anyone special and John told Doug about me. He promised me he didn't give too much detail other then at how happy he was. That made me feel good.
So I asked why would he want Doug to meet Cheryl? John told me that if we were ever going to have a threesome, he'd want Doug to be the third because he knew he was a very good guy, was safe and most importantly discreet. It had been a few weeks since John had bought up the threesome topic so I thought he may have forgotten about it. I didn't tell John, but I did on a couple occasions jerk off while thinking about it, but I thought if I told him he would push for it. As excited and into it I was, I didn't want to let on. So I asked that if that ever did happen, to tell me about Doug. John told me Doug was a few years older then him, over 6' tall and about the same body size and weight as him. He never saw him naked so he couldn't tell me about that part. I told John I would hope to always be with him and that it didn't really matter. I didn't even ask to see a picture.
John then asked me if I would be willing to go to Pennsylvania with him next weekend. This was a huge step, I started asking questions but John said he had everything planned out for me not to worry. We'd travel down Friday just for the night, he got a 2 bedroom suite since we've never actually 'slept' together and I would have a room to change in in private and Doug would never see me as me, just Cheryl. I asked him if he was 110% positive that he really wanted to share me in a threesome to which he said 90% sure. I trusted John so I said OK.
We arrived at the hotel at 6:30, it was less then 75 minutes away from home so the anxiety wasn't too bad to handle. As soon as we got to our room I at John's suggestion went to get dressed comfortably sexy, he suggested lingerie. Doug was arriving at 7:30 and John was putting the 6 bottles of wine on ice. I took a quick shower and started to get ready for I didn't have much time. Applying make-up still took me a while. I had my outfit picked out. My fav 4” black high heels with ankle straps, black thigh highs and g-string. I also had matching black satin chemise and long black satin robe. I put on my brunette wig, hoop earrings and fake diamond necklace. I went a little darker with the make-up, a deep dark purple lip stick and eye shadow. I wanted to look mature and sexy.
Before I was finished I heard Doug arrive, he and John were talking and suddenly I started to get a bulge. I took a minute to relax since all that was left was to walk out there and I wanted to compose myself. I've been practicing my walk and voice for weeks and wanted them both to be perfect. I practiced both while looking into the mirror and when I had them down I decided it was time to enter the living room.
As I walked out my room John said "Hey, beautiful" and introduced me to Doug. OMG, he was gorgeous. He had that sexy manly mature look that made girls wet or in my case, my ass relaxed to be entered. We kissed each other on the cheek, with me in heels we were the same height, and I said I was pleased to met him, John has mentioned him numerous times. He told me I looked stunning. John suggested we sit down and have some wine. As John handed me my first glass he whispered in my ear how my voice turned him on. John was so special making me always feel good.
John was the perfect gentleman filling everyone's glass the whole evening. I think he wanted us all to get drunk to get things rolling. We had a very pleasant conversation and after the 2nd bottle the conversation started to get a little more risqué. John was sitting next to me rubbing my crossed legs softly and I saw Doug several times checking out where John's hands were as well as my legs so I started rocking my foot back and fourth to get more of his attention hoping that might be getting him horny. I was getting horny myself just thinking about what was going to happen so I placed my arm under John's and started rubbing the inside of his thigh. John started to bulge slightly and after he paid me a compliment to Doug I asked him to look at me and planted a soft tender kiss on his lips. I felt his bulge hit my arm so I knew it had worked.
Doug commented on how good we look together and I said, yes, there are many things that we were good together at especially the hot sex. I could tell they both couldn't believe I just came out and said that but I felt the need to get things going myself. John thanked me and started kissing me. We were making out and softly caressing each other. After a minute John pulled away to comment how it is rude to leave out our guest and asked if we should go into his room. Doug said that was a good idea and he'd bring in a bottle of wine. John held my hand as he lead me into his bedroom. His palm was sweaty so I knew he was a little nervous. I walked in and put down my glass as John suggested that maybe Doug and I should get to know each other a lil better. I turned to face both men and slowly untied my robe and pulled it so it would fall to the ground.
Doug said wow. I walked up to Doug and we started making out. He had his hands on my ass in seconds and was rubbing and grabbing my ass cheeks. It was hot. I looked at John and he was busy putting lube and condoms out. Watching us kiss must have got him all horned up. I kissed Doug again and he pulled me closer. I felt a huge bulge in his jeans and felt the need to investigate. I slowly dropped to my knees, unzipped him and pulled it out. OMG, it was at least an inch and a half longer then John's, and a lil wider. I licked the tip and as I started taking it into my mouth slowly started stroking it. It was delicious. It was so big I started gagging a little while trying to take more of it in. John asked me if I liked it and I told him yes.
I told Doug to lay back on the bed and quickly turned to John who was standing naked next to me and took him into my mouth. He was as hard as I had ever felt him so I didn't suck him too long. I knew he was going to cum quick in all this excitement and wanted him in my ass most of that time. I moved up onto the bed and got back to working on Doug's big cock. I left my ass hanging at the beds edge so John could fuck me from behind. John gently pulled aside my g-string as he entered my man pussy slowly. Between that and having Doug in my mouth I myself was in heaven and hard as hell.
Doug placed a hand on my head to lightly control the motion of me sucking on him. Doug and John were both moaning as I tried to get as much saliva on Doug's cock to make it as wet and warm as possible as I was quickly sucking him. His size let me use my hand to stroke him at the same time. I was impressed by John as he took his time on my ass with nice long slow strokes. It felt wonderful. I knew if I moaned John would shoot but I couldn't control myself in all the excitement and took my mouth off Doug's cock briefly to only ask John to “Fuck me baby, keep fucking me” in a mild girlish tone. As if on queue John started grunting as he pumped me a few times harder and let us know he was cumming. The rock hard cock in my ass felt awesome while I continued to work on Doug with my hand and mouth. John pulled out of me, yanked off the condom and shot all over my ass. I felt his warm sperm being rubbed in my ass by his softening cock.
I looked at Doug and asked him if it was time to put on a condom. He said it was. As Doug put on a condom I moved myself up on the bed to lay next to him. John commented at how great that felt while watching me suck Doug with a big smile on his face. Doug was quickly ready as he positioned me onto my back and himself between my legs. He raised my ankles upon his shoulders and took off my g-string which now exposed my opened my ass and after John handed him lube which he squirted some on both my ass and his cock, he guided his large cock to my gaped ass. He entered me slowly and asked if I was ok as I grimaced a lil bit. I told him it was fine and to enjoy me. Doug started slowly and after all seemed good he quickened his pace.
John stood a few feet away from the bed lightly stroking his cock and said “Cheryl, you look so beautiful right now”. I smiled at John while enjoying Doug's large cock working my ass. I reached out to grab John's cock and pulled it to me to put in my mouth. His semi erect cock felt good in my mouth as Doug kept pumping away. He let go of my legs so I wrapped them around him to keep him close. Doug started grunting a lil louder and I asked him to cum on me when he felt the urge. He kept pumping away for several minutes. I continued to suck John's now hardening cock. Doug looked into my eyes as I was starring directly into his as I played with John's cock with my mouth. I knew that excited him as he pumped me harder and harder the more he watched. Shortly after his fastest pumps he pulled out and ripped off his condom. I let John's cock out of my mouth as I begged Doug to cover me with his cum and he did. I quickly felt a large warm load covering me as I reached down to rub it in while saying “Yes baby, that's it, get it all out”. All the while Doug and my eyes were locked together.
Before I could even enjoy this very intense moment being shared between Doug and I, John reached out and pulled my head towards his cock and he was stroking himself to another orgasm. I opened my mouth as John grunted and I felt a trickle hit my face. It was a small load but the look on John's face told me it was a powerful one. I took him into my mouth to gently coax him while he softened in my mouth. He said "holy shit" as he was regaining his composure. John has never cum twice that quickly before while with me alone so I knew that this experience had have excited him beyond belief.
The three of us laid on the bed together and had several soft kisses. All mentioning how great it was. John then went down on me to reward me for the great time we just had. As John was sucking me off I looked up at Doug as we again locked eyes together. He reached out and held my face so gently. Doug and I seemed to quickly develop this unmentionable deep desiring lust for each other. I would just melt looking into his eyes. He leaned over and we started making out. I was so excited by Doug that I quickly began gyrating my hips as John was sucking me and I cried out “Oh yes” as I shot my load into John's loving warm mouth. In seconds I felt so guilty because it was the Doug I was thinking about as I came. I closed my eyes and let my head hit the pillow as I just laid and relaxed.
After a while Doug said he'd better take off, he had a busy day ahead as we were all getting out of bed. I mentioned how I was exhausted, worn out and a lil sore and needed to go get some sleep. I told Doug it was a pleasure meeting him again as I kissed him softly good night. I then walked over to John and tenderly kissed him good night. I picked up my robe and asked John what time we were leaving the next day. He said 10 so I told him I'd see him then. I told the guys to have fun and headed off to my room.
As soon as I got there, I took off my heels and wig and went straight under the covers. I started to go over everything that happened that night in my mind. I felt so guilty but didn't let that bother me ask I jerked off thinking about Doug one last time that evening. My orgasm felt great as I shot it out on my groin and then just closed my eyes and fell fast asleep.
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