Synopsis: I as a young boy (me) lived in the conservative Midwest starts on his life long journey of the joy of cross dressing and his deep desire and lust for silky sexy nylons. Soon he starts to learn with much encouragement what it's like to be a girl from his Mom's best friend!
My First Nylon & Girdle Experience By Jamie R.
Written & Published Exclusively for Sheer Delight (trannycafe.com) Copy write 1998-2008 by Jamie R. of T. H. Ent. ALL Rights reserved and property is absolutely not to be posted, printed, or used in ANY way other then by readers for own their personal use.
My TRUE STORY! I as a young boy (me) lived in a conservative Midwest town starts on his life long journey of the joy of cross dressing and his deep desire and lust for silky sexy sheer shiny nylons! While this part of the story is complete. I am writing the continued journey he makes after the first time! More of my true and fantasy stories about cross dressing, nylon stockings, pantyhose and smoking fetish are available on my T-girl fetish web site, TrannyCafe.com. Opening fall 2008 Kisses! Jamie
Part III (Becoming a real girl and not just a cross dresser) Well, the next big event happened when I went over to play with the boys (more like see sexy Sally to remind her of our weekend if she saw me) and found them not home. Sally's current steady boyfriend was home and told me to come on in but the boys went with their Mom to the beach. I was about to leave when he asked me if I wanted something to drink and watch some TV with him. I said sure and went to the living room and sat on the couch. I was not paying much attention but as Bob (not his real name) came in, he handed me the drink and I thanked him as he sat down next to me. We watched the show and than after a few minutes, he asked if I could do him a huge favor. I did not know what he had in mind but said sure. He said he had heard of my little adventure in the bathroom from Sally and thought it was cute. My mouth dropped to the floor and the blood went right to my face! I could not believe Sally had told him but I quickly remembered she told me she would not tell my Mom. She never mentioned not telling anyone else. I was speechless but Bob saw the embarrassment I was dealing with and he quickly told me that he did not think it was a bad thing. What? Did I really hear him say that? Wow. This made me feel a TINY bit better but I was still pretty blown away. The next thing he told me almost knocked me right over! Bob said he wished he was there that day and could have seen me and in fact he would give me some money if I went in the bathroom and changed into what I was wearing that day and "model" for him. Pay me? Wow! I was at this point so much in a state of shock that I did not know what to say or do but I knew that he said he was ok with me dressing that way and that he offered me $$$ and finally, I have been dying to try it on again since that day! I let out a meek ok. He said ok, well Sally and the boys would be gone all day so get started and we can have a little fun. I got up with my numb body barely responding and went back into the "den of lust" of my desires (the bathroom) and behold there were all of Sally's finest again! My heart skipped a beat or two and I quickly stripped my clothes off to be totally naked and than went to her hamper to see if she left me any fragrant item to hold up those yummy nylons. She of course did not disappoint me again! I found a very sexy garter belt and it was very femm and lacy. I also found a very nice slip with lace around the bust to match my garter belt. I then chose a pair of her coffee colored stockings off the rod. I sat down to roll up the nylons on my young hairless legs and melted with the feeling of them on my skin again! I was soooo hooked to enjoy doing this forever! Next I put on a matching pair of panties and the garter belt and than threaded the straps through the panties in case I had to take them off to go potty. I attached the clips to the nylons and than smoothed those yummy items on my legs loving the feeling! I than put on Sally's silky short slip that just barely covered the tops of my stockings. I felt so sexy and hot! I also was sooo afraid to open the door and go back in with Bob. I than worked up my nerve and after all he told me her would give me money. Bob was sitting on the couch very relaxed watching the TV when he looked up and saw me standing there in my pretty attire. His mouth went open and than he sat up and said WOW! It made me feel wonderful that he clearly like it. I was lightly shaking and was embarrassed beyond imagination but the funny thing is I also felt very very good and feminine! So as I started to relax by his obvious approval and him telling me I looked GREAT! I started the agreed " fashion show" and did what I have seen on so many pageants on TV. I made like there was a run way and modeled walking away from him and back and even tried to move girlie. This was so much fun and the nylons were making their sexy swishing whispers. It really was becoming so very nice and I felt more and more relaxed dressed this way. Bob kept encouraging me and telling me what a great model I made. He told me that I had great legs and my outfit made my butt look very feminine and nice. I just got more into the part and was on a cloud as I wiggled my body more like a girlie girl. As I made my way for about the forth time away from Bob on the couch I turned and my whole fantasy girlie bubble burst! Bob was still sitting on the couch but had his pants open and this big penis in his hands. He was looking at me with total lust in his eyes like I was a steak on a plate in front of a hungry man just out of the desert island for 6 months living on only coconuts! I stopped in my tracks and my mouth fell open. The fear rushed back into my body and I felt the blood in my face again. I did not know what to do. I never saw a penis that big. It had to be three times bigger than mine. Bob told me he was sorry but I looked so nice and don't be scared. He was just very turned on by my modeling and my legs in the sheer shiny coffee nylons. I just stood there not saying anything or moving. Bob said it's ok and to come sit on the couch next to him as he patted the seat with his free hand. I did not respond so he tried again to reassure me and once again invited me to come by him. I stated to slowly move closer and could see more of his huge semi hard penis in his hand that he continued to slowly stroke. I gingerly sat next to him and my eyes were locked on his meat. It looked unreal and something in me would not let me take my eyes off it. He asked me if I thought it was nice. I shook my head lightly yes. He than asked if I wanted to help him. I was scared but excited inside beyond explanation! I surprised myself and again shook my head yes. Bob wasted no time by taking my little hand in his as he said he would pay me more if I can help him feel better. I still said nothing. Bob told me that I was soooo sexy and looked sooo good in my lingerie and silky nylons that he was never so turned on. He told me that I was a the perfect model and I should dress more often cause I was a natural. All his words came to me and registered but I was still locked in my gaze on his COCK! I watched my hand get closer and than I felt my first cock other than my own. Oh my! It was hard but soft and so smooth. Bob wrapped my hand around it and got me started to stroke him and than removed his hand. I was watching his head of his cock pop in and out as I skinned back the foreskin. That was amazing as I was circumcised and never saw a cock that looked like that. It looked so incredible. I started to relax and Bob just kept telling me how good that felt. I was hypnotized and was enjoying touching it. I also noticed some cloudy liquid forming at the tip as it became harder and harder in my hand. It no longer had extra skin and it was longer and very defined. It was 8.75" long (as I found out later) and it was fairly thick but not too much and it tapered to a point at the head. It was unreal and I just kept pumping him looking at this incredible monster in my delicate hand! Bob said I was doing so well and asked me if I wanted to make even more money. I did not look at him but quietly asked how? He said if I kissed it and put it in my mouth he would pay me more money. I quickly shook my head no. Bob asked if I did not like his cock and I said yes. He said he would give me twenty dollars if I would kiss just the top and for the modeling. I did not respond. He again encouraged me and told me he knew I wanted to and it was ok. He than took his hand and placed it around my head and slowly pulled my head down to his cock. It was right in front of my tender lips and the goo was so tempting. I slightly opened my lips and moved in to kiss the tip. As I did the liquid spread across my lips and I got my first taste of precum. I liked it even if it was a tiny bit salty and Bob just moaned with delight. I wanted more so I again kissed it and tried to taste more of him and he again took his hand on my head and gently pushed me into his cock so more of the head slid across my lips and into my mouth. I could feel my own cock was very hard in my panties now and I did not want to stop! I willingly took more of him in my mouth and while I was still scared, I was excited beyond words. He kept telling how sexy and pretty I was and he started to buck his hips to move his cock in and out of my mouth. He asked me if I wanted to be his special girl. I just shook my head yes as I continued to give him my first blowjob. I got more and more into the role and REALLY enjoyed sucking him. He kept moaning so I knew I was doing a great job. I wanted so much to please him! Bob told me to lick around the shaft and take my hand and play with his balls as I sucked him. I did and they felt equally as nice and foreign. He told me something that made me turn a corner in my life forever! Bob told me that I not only looked great in my sexy girlie clothes but that I was a wonderful cock sucker! I loved that! I wanted to be that! I wanted to do this forever! I continued to suck his cock like I was on a mission. Then it happened. I felt Bob tense up and move his hips up as he told me that I was going to make him cum and to be a good girl and not let any liquid fall on the couch! I than felt his cock swell in my young mouth and than a flood of cum filled my mouth and some went down my throat! I did not know what to do and backed off as the last of his sperm hit me in the face. I was like a deer in the head lights but I knew I did something right! Bob moaned loudly and than took his hand to finishing milking the last of his cum to the tip of his beautiful cock. He asked me to lick it off so not to waste it and I eagerly did so as I really loved the taste. Bob told me I was a very good girl and than he took his finger and wiped off his cum still on my face and said open baby to feed it to me. Bob asked if it tasted good and I quickly shook my head yes with a light smile on my face. He said good cause he would love to give me more in the future. I just said ok. Bob pulled me next to him and wrapped his strong arms around me as we sat side by side for him to recover. I felt like his girlfriend and it was really nice, safe and warm there. He kept telling me how sexy I looked and that was sooo wonderful what I did for him. He asked me if I enjoyed being a sexy little cock sucking girl. I said my first words other than yes, I told him I would love to do it more. Bob just smiled and told me he was very happy to teach me everything I need to know to be the best and hottest girl. I said ok, that would be wonderful. Bob got up to get a drink and I just watched him as he dropped his pants and took off all his clothes. He walked to the kitchen and his semi hard cock just bounced wildly as he did. I knew I would be getting more of that beautiful cock again soon! I watched TV as I sat like his little girlfriend on the couch waiting for him to return. I gently rubbed my own still hard cock thinking how lucky I was and how much I enjoyed what just happened to me and be a girl! I forgot all about the money! Bob returned with a drink and one for me. He noticed that I had a stiffy in my lingerie and told me that it's ok if I want to play with my self cause I earned it for being a very good girl. I smiled and pulled out my little cock and started to stroke it in front of Bob as he drank and just smiled at me with loving eyes. He said he hoped I had fun being a girl cause he really loved having me as his special girlfriend. It would be our little secret and he said if I ever wanted to suck his cock again all I had to do is ask. He had NO idea how happy that offer made me or how much I would take him up on that! The thought of it and all that happened was getting me ready to cum too. I was building to probably a huge orgasm but just than Bob told me to wait. I snapped out it at the height of my lust to see he was again stroking his beautiful cock. I looked at him as to ask him why he stopped me and he asked if I wanted to make it an even $25 and learn something REALLY good. I said ok as my trust was now very high with him and I wanted to please him and $25! Wow! He knew I was sooo turned on at this point that I was ready to take on the football team if he asked. He told me to first come over and kiss his cock again which I quickly and hungrily did for him because I loved it! He than said as I sucked him, he wants me to stand up and stand between his legs. I sadly let lose of his cock with my mouth and did as my man asked. He smiled and ran his hands all over my waist and than down to my silky nylon covered legs. I felt electricity as he touched them through the thin nylon. I LOVED this feeling. I was becoming more and more sure that I wanted to dress like a girl forever! I also knew I wanted to be Bob's girlfriend too! He could do anything with me and I would dress however he was pleased. He than told me to turn around and than he ran his hands across the soft slip covering my butt and that also felt wonderful. He said I should get ride of the panties witch I did. As I bent over to take them off my feet I felt his hands go under my slip and rub my naked butt and it was wonderful. He told me to stay bent over for a bit and told me I have the sweetest little ass. Anything I can do to please him was all I wanted. I moaned as he lightly rubbed it and grabbed it now and than. He than said to wait a second as he reach for something on the lower self of the night stand next to the couch. As he sat back up he told me to stay like I was and that this was going to be a little wet and cool but don't move. I said OK with a "I will do ANYTHING you want" tone in my voice! He than took his finger with something wet, cool and slippery on it and he started to enter my butt. I was sooo confused but I trusted him as he worked his long adult finger in me deeper and than I felt him add another finger. He slowing moved his fingers back and forth and it started to feel wonderful so I moaned lightly and pushed my butt against his hand. I wanted him to keep doing this and wanted him to know I liked it. He sure did and than asked me if I was ready to become a real girl. I did not know what he meant but being I had not cum yet and I was at the height of my excitement and lust I said I did. He told me to turn around as he slowly drew his fingers out of my ass even if I did not want him too. I did as I was told and he told me to kneel on the couch with my legs lightly spread. I did as he got up off the couch and got behind me. He told me to bend over again as he used his hand on my back to guide me. I was than with my butt in the air and he told me to just relax and trust him. He told me that this would hurt a little for a little bit but would soon feel really good and be worth it. I was again scared but as before, I trusted him and did as I was told. He told me to push out like I was taking a poop when I feel him against me. I thought he was going to stick his fingers back in but I than felt his beautiful cock at my rosebud. He very slowly started to push into me and made little stops. He kept asking if I was ok and I shock my head yes. Hurt a little? OUCH! It was hurting a lot and was about to tell him to stop when I felt a pop and than he glided much deeper in my tender little butt. I still hurt but it was not as bad and I felt like I had to take a poop. I let my man do as he wished with my ass and soon I felt his body right next to my ass. He had that huge cock all the way in me but was not moving. Bob told me he wanted me to again relax and get used to it in there. He then started to pull out and then in and again out and back in. His hips started to move in rhythm more and more fast and the pain was going away fast! In fact, I was moving my ass to meet him. I started to feel as he promised! It started to feel soooo good! I wanted it more and he was now thrusting in me and out full speed. He told me what a sexy girlfriend he had and I loved every word as I loved this man's cock. He kept fucking me and I kept telling him yes! I told him I wanted more! He told me I was his special girlfriend and that he was going to do this and have me suck his cock often while dressed sexy for him. I told him I wanted that sooo much! What felt like hours (actually about 10 minutes) I felt Bob's body tense up again and he told me he was coming in me! I told him yes, please! I wanted to feel him explode in me! He wasted no time to my request. I felt his body jerk and than a wonderful warm flood of his delicious cream fill me deep inside! Than something I did not know could happen, I cam in an explosive orgasm all over the couch and I NEVER even touched my own cock! We both collapsed and he reached for some tissues to wipe my cum off of the couch. I was soooo satisfied and felt soooo wonderful and relaxed. I was very happy how my life was turning more and more interesting and exciting. I just loved being a girl and I loved this man who was helping me become one. He was a great lover. Even at that age, I knew this to be so! I wanted to be his girl whenever he wanted me! He made me feel so wonderful inside when he told me that was some of the hottest sex he has ever had. He also told me that some girls and even some "special girls" like me were made to be a "man pleaser". He said I was a natural and born to suck cock and born to get fucked. I was soooo happy! Bob told me I had better get changed back and run along to my house so I don' t get in any trouble and reminded me that what happened MUST be between me and him! I said, I understood and went to change. When I was back in boy mode, I went to my new lover and kissed and hugged him to thank him for a wonderful experience. He than also reached in his pocket and handed me $25 dollars. I had forgotten all about that and it was very nice to make for a perfect time! I guess it was the start of my future as a "kept" girl. After the time of my life and feeling wonderful with Bob's cum slipping from my ass, I floated home on a cloud and wondered if I would be able to do that again, SOON! As it turned out, Bob left the next day for his business and I did not see him again for a few weeks. I missed him so much! I wanted his cock in my mouth and ass again! I wanted to taste his wonderful sperm again! ~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~ I hope you enjoyed this third part of my autobiography on how I started my journey into the erotic and wonderful world of being a T-girl and how I fell in love with yummy, silky, sheer, & shiny nylons and how I became a Virginia Slims girl! Your feedback is very much appreciated and I would like to know if I should post more chapters of this on going part of my life that was the best years of my life! Kisses Jamie (_Jamiebitv@aol.com_ (mailto:Jamiebitv@aol.com) )