Mr. Peterson and the part time sissy.
I can remember one time in particular that, to this day, still remains one of my favorite sexual encounters. The weekend I spent cross dressed for Mr. Peterson and three of his friends was three days of pure bliss.
I had been Mr. Peterson's toy for more than a year by this time and was very much getting into being a sex object. Leaving my house early for school to swing by and suck his cock was a routine experience. It was a good thing, he went to work relaxed and I went to school with a belly full of cum.
It was a Monday morning and I was busy working for my breakfast when Mr. Peterson mentioned the weekend at the lake. He told me that he wanted he and I to spend the weekend at the lake, relaxing and having sex outdoors. I hurried up and got him to feed me his load and agreed to the plans. I never had any trouble going away for a weekend with Mr. Peterson as my parents thought he was a good influence on me.
The remainder of the week seemed to take forever, but Friday morning finally arrived. I left my house for school with my weekend gear (not that I thought I would be wearing much clothing) to keep my parents clueless. I think that particular school day lasted about three centuries before I could finally get out. He picked me up at school and off we went.
We got to the lake house in great time and I was surprised to see other cars parked in the driveway. Mr. Peterson mentioned three of his friends were going to be relaxing at the lake with us this weekend. This was big, I'd only ever slept with Mr. Peterson alone or with one other man, now I was spending a weekend with four.
We head inside and I meet his friends. Mssrs Jones, Smith, and Flannery all seemed quite pleased to meet me. We all sat down and Mr. Peterson and I unwound from the drive up. They talked business between themselves for a bit before Mr. Jones asked if Mr. Peterson thought I would do what they had discussed.
Mr. Peterson laughed and said "Sean is one of the most sexually open minded people I've ever had the pleasure of meeting". I blushed tremendously at the compliment. Both Mr. Smith and Mr Flannery called me cute for blushing, laughing all the while.
"Sean, the four of us have a very special request to make of you this weekend." Mr. Peterson said as he pulled out the first of countless joints that burned while we were there. Over the past year I had learned that "special requests" were things that might initially make me uncomfortable but rapidly turned out to be things I really enjoyed.
I smiled and said, "What interesting activity did you all have in mind?". Mr. Flannery smiled and replied "Well all of us here like girls as well as boys and we also like it when the two are combined." I looked at the four men in the room confused, remember I was a pretty naive guy. "Combined? How would you combine girls and boys?" I asked. Mr. Jones laughed and pulled out a suitcase I had not noticed before then. "Well the easiest way is to have a boy like you wear girls clothes while we have sex." Mr. Smith followed quickly with "We would like for you to dress up for us this weekend Sean. I am pretty sure all of us would agree it would be very sexy."
I was stunned at their request. Looking back I consider myself lucky that I never subscribed to the "manliness" bullshit that gets thrown around so profusely. "So you want me to dress up like a girl, so panties and a bra and stuff?" All four quickly nodded their heads as Mr. Jones opened the suitcase. Inside were all sorts of lingere and a few short skirts and sheer tops. There was a small case under all the soft silky items that I found contained a make up kit. They were apparently completely prepared to turn me into their little girl slut for the weekend.
Looking at everything and thinking about how much I do enjoyed being a bottom it only took me around 20 minutes or so to agree to their request. To say they were thrilled was a bit of an understatement. We smoked another joint and I headed to the bathroom to get clean. Mr. Smith joined me in the bathroom. He told me that he wanted to prep me for the evening. He had the make up kit with him and a grocery bag. From the grocery bag he pulled a couple of bottles of Nair and a rather fancy enema bag.
Fast forward about an hour or so and I was hairless from the neck down and sparklingly clean. Mr. Smith led me to one of the spare bedrooms and sat me down in front of a mirror. He proceeded to give me a lesson on make up and how to put it on. He commented on how it was nice my hair was long, so that I did not need to wear a wig. Make up finished he did a little work with some hair spray and a brush on my hair. He picked out a nice powder blue matching set of bra and panties along with a short black skirt and one of the sheer tops. "Put this on and come out to the living room when you're ready. You're going to look fabulous and I think you'll enjoy being our little sissy slut this weekend."
I looked at the lingerie and shook my head. What was I getting myself into? I picked up the panties and was shocked at how they felt as they slid up my hairless legs. I tucked myself in as best I could as I was rapidly getting a hard on. The bra felt just as good on my hairless chest as the panties did on my lower half. I finished getting dressed and sat back down in front of the mirror. I'm not going to say I looked just like a girl or anything but I did look pretty good. I could have passed in a dark room or from a distance perhaps.
Gathering my courage I walked out to the living room where my four grown men were waiting. Thinking to myself I realized I was going to enjoy being a complete slut this weekend. This put a little spring in my step as I stepped into the living room and the conversation died. I smiled shyly at the men as they all began talking at once. "You look fantastic, I can't wait to bend you over, those lips are going to look so good covered in cum." I was already high from the pot and the compliments were going to my head. I heard myself say "Well gentlemen I think I should repay you for your compliments, let me suck your cocks now."
The speed with which I was fed those first four loads reinforced the idea that this was something that they had all been looking forward to for quite some time.
Before I knew it I was standing on the deck overlooking the lake, my panties pulled to the side and Mr. Flannery's cock buried balls deep in my ass. I did my best to pitch my voice so that I sounded more feminine while he pounded me deep. My legs were shaky at this point so it was a good thing that Mr. Smith was kneeling in front of me, swallowing every inch of my own cock. I didn't know how much longer I could take the joy of getting sucked while I had a nice big cock filling me from behind. I groaned out and shot everything I had down Mr. Smith's throat while Mr. Flannery rode my ass to his own. Feeling his cum fill me as mine shot down Mr. Smith's throat will go down as one of the best feelings I've ever had during sex.
Over the next couple days I really got into my fantasy persona and by Saturday noon I would only respond to the name Molly. If these gentlemen wanted a girly boy this weekend I would do my best to make sure that is exactly what they got.
The weekend was a hit for everyone. I was the best sissy cum slut those men ever had. I did notice that Mr. Peterson really seemed to enjoy watching Mr. Jones fuck me with his 10 inch black cock. Once I got used to his entire cock inside me I couldn't get enough. I made sure to sleep in Mr. Jones' bed the entire weekend so that I could suck and get fucked by him first thing every day.
Putting on my boy clothes at the end of the weekend was actually rather disappointing to me. I really had enjoyed being a sissy. On the drive home Mr. Peterson told me how happy he was I had agreed to their fantasy weekend. I just smiled as told him that I thought that I probably had even more fun than they did. Rather than wake my parents when we got back into town Sunday night I just slept at Mr. Peterson's house. As I lay snuggled up to him he told me that Mr. Jones had invited us to come downtown Chicago and "party" with him and some friends. "Yes, please" is all I said as I wiggled my bottom until Mr. Peterson's cock was firmly pressed into my crack. sleep came quickly.
It turns out it ended up being Mr. Jones who would introduce me to the "bathhouse". The weekend we spent with he and his friends was pretty stellar as well. Sneaking into the bathhouse while u******e just added to the thrill of having a large audience watch me bottom.
I had been Mr. Peterson's toy for more than a year by this time and was very much getting into being a sex object. Leaving my house early for school to swing by and suck his cock was a routine experience. It was a good thing, he went to work relaxed and I went to school with a belly full of cum.
It was a Monday morning and I was busy working for my breakfast when Mr. Peterson mentioned the weekend at the lake. He told me that he wanted he and I to spend the weekend at the lake, relaxing and having sex outdoors. I hurried up and got him to feed me his load and agreed to the plans. I never had any trouble going away for a weekend with Mr. Peterson as my parents thought he was a good influence on me.
The remainder of the week seemed to take forever, but Friday morning finally arrived. I left my house for school with my weekend gear (not that I thought I would be wearing much clothing) to keep my parents clueless. I think that particular school day lasted about three centuries before I could finally get out. He picked me up at school and off we went.
We got to the lake house in great time and I was surprised to see other cars parked in the driveway. Mr. Peterson mentioned three of his friends were going to be relaxing at the lake with us this weekend. This was big, I'd only ever slept with Mr. Peterson alone or with one other man, now I was spending a weekend with four.
We head inside and I meet his friends. Mssrs Jones, Smith, and Flannery all seemed quite pleased to meet me. We all sat down and Mr. Peterson and I unwound from the drive up. They talked business between themselves for a bit before Mr. Jones asked if Mr. Peterson thought I would do what they had discussed.
Mr. Peterson laughed and said "Sean is one of the most sexually open minded people I've ever had the pleasure of meeting". I blushed tremendously at the compliment. Both Mr. Smith and Mr Flannery called me cute for blushing, laughing all the while.
"Sean, the four of us have a very special request to make of you this weekend." Mr. Peterson said as he pulled out the first of countless joints that burned while we were there. Over the past year I had learned that "special requests" were things that might initially make me uncomfortable but rapidly turned out to be things I really enjoyed.
I smiled and said, "What interesting activity did you all have in mind?". Mr. Flannery smiled and replied "Well all of us here like girls as well as boys and we also like it when the two are combined." I looked at the four men in the room confused, remember I was a pretty naive guy. "Combined? How would you combine girls and boys?" I asked. Mr. Jones laughed and pulled out a suitcase I had not noticed before then. "Well the easiest way is to have a boy like you wear girls clothes while we have sex." Mr. Smith followed quickly with "We would like for you to dress up for us this weekend Sean. I am pretty sure all of us would agree it would be very sexy."
I was stunned at their request. Looking back I consider myself lucky that I never subscribed to the "manliness" bullshit that gets thrown around so profusely. "So you want me to dress up like a girl, so panties and a bra and stuff?" All four quickly nodded their heads as Mr. Jones opened the suitcase. Inside were all sorts of lingere and a few short skirts and sheer tops. There was a small case under all the soft silky items that I found contained a make up kit. They were apparently completely prepared to turn me into their little girl slut for the weekend.
Looking at everything and thinking about how much I do enjoyed being a bottom it only took me around 20 minutes or so to agree to their request. To say they were thrilled was a bit of an understatement. We smoked another joint and I headed to the bathroom to get clean. Mr. Smith joined me in the bathroom. He told me that he wanted to prep me for the evening. He had the make up kit with him and a grocery bag. From the grocery bag he pulled a couple of bottles of Nair and a rather fancy enema bag.
Fast forward about an hour or so and I was hairless from the neck down and sparklingly clean. Mr. Smith led me to one of the spare bedrooms and sat me down in front of a mirror. He proceeded to give me a lesson on make up and how to put it on. He commented on how it was nice my hair was long, so that I did not need to wear a wig. Make up finished he did a little work with some hair spray and a brush on my hair. He picked out a nice powder blue matching set of bra and panties along with a short black skirt and one of the sheer tops. "Put this on and come out to the living room when you're ready. You're going to look fabulous and I think you'll enjoy being our little sissy slut this weekend."
I looked at the lingerie and shook my head. What was I getting myself into? I picked up the panties and was shocked at how they felt as they slid up my hairless legs. I tucked myself in as best I could as I was rapidly getting a hard on. The bra felt just as good on my hairless chest as the panties did on my lower half. I finished getting dressed and sat back down in front of the mirror. I'm not going to say I looked just like a girl or anything but I did look pretty good. I could have passed in a dark room or from a distance perhaps.
Gathering my courage I walked out to the living room where my four grown men were waiting. Thinking to myself I realized I was going to enjoy being a complete slut this weekend. This put a little spring in my step as I stepped into the living room and the conversation died. I smiled shyly at the men as they all began talking at once. "You look fantastic, I can't wait to bend you over, those lips are going to look so good covered in cum." I was already high from the pot and the compliments were going to my head. I heard myself say "Well gentlemen I think I should repay you for your compliments, let me suck your cocks now."
The speed with which I was fed those first four loads reinforced the idea that this was something that they had all been looking forward to for quite some time.
Before I knew it I was standing on the deck overlooking the lake, my panties pulled to the side and Mr. Flannery's cock buried balls deep in my ass. I did my best to pitch my voice so that I sounded more feminine while he pounded me deep. My legs were shaky at this point so it was a good thing that Mr. Smith was kneeling in front of me, swallowing every inch of my own cock. I didn't know how much longer I could take the joy of getting sucked while I had a nice big cock filling me from behind. I groaned out and shot everything I had down Mr. Smith's throat while Mr. Flannery rode my ass to his own. Feeling his cum fill me as mine shot down Mr. Smith's throat will go down as one of the best feelings I've ever had during sex.
Over the next couple days I really got into my fantasy persona and by Saturday noon I would only respond to the name Molly. If these gentlemen wanted a girly boy this weekend I would do my best to make sure that is exactly what they got.
The weekend was a hit for everyone. I was the best sissy cum slut those men ever had. I did notice that Mr. Peterson really seemed to enjoy watching Mr. Jones fuck me with his 10 inch black cock. Once I got used to his entire cock inside me I couldn't get enough. I made sure to sleep in Mr. Jones' bed the entire weekend so that I could suck and get fucked by him first thing every day.
Putting on my boy clothes at the end of the weekend was actually rather disappointing to me. I really had enjoyed being a sissy. On the drive home Mr. Peterson told me how happy he was I had agreed to their fantasy weekend. I just smiled as told him that I thought that I probably had even more fun than they did. Rather than wake my parents when we got back into town Sunday night I just slept at Mr. Peterson's house. As I lay snuggled up to him he told me that Mr. Jones had invited us to come downtown Chicago and "party" with him and some friends. "Yes, please" is all I said as I wiggled my bottom until Mr. Peterson's cock was firmly pressed into my crack. sleep came quickly.
It turns out it ended up being Mr. Jones who would introduce me to the "bathhouse". The weekend we spent with he and his friends was pretty stellar as well. Sneaking into the bathhouse while u******e just added to the thrill of having a large audience watch me bottom.
9 лет назад
