Date: Sat, 5 Jan 2019 04:01:28 +0000 (UTC) From: Happy Gilmore Subject: How it all started a TG story I remember back when I was just a teenager. My hormones were raging. I had a crush on my best friend's older sister Angie. She was 17 to my 14. She was gorgeous. She was what every 14 year old boy wanted, but she had a boyfriend that was a senior. One day while over at my friend's house I needed to use the bathroom. My friend said to use the bathroom that he shared with his sister. I had never been in this bathroom before for if I needed to go I used the ½ bath on the first floor but this time we were in his room working on a school project. When I went in to the bathroom it was the typical bathroom: tub and shower enclosure, two sinks, small storage area for clean towels, mirror, toilet etc. One sink was clearly one that my friend used and the other was clearly his sister's but it was nothing out of the ordinary. What was out of the ordinary was that this bathroom contained a dirty clothes hamper with an ill fitting lid. After doing what I went into the room to do and after washing my hands I accidently hit the hamper and the lid fell off. Embarrassed I picked up the lid and I was setting it down saw the most gorgeous pair of black and white panties at the top. My heart beat was faster. Underneath those panties was a bra that matched the panties. I couldn't resist. I picked them up and the material was something that I had never felt before. She soft and so pretty. For some reason I had to have them. My hormones kicked right in. I took the panties and the bra and stuck them in my pocket of my hoodie. It was almost time to leave for it was soon to be dinner and just before I left I saw Angie downstairs. We had small chat but I am sure I was sweating and hoping not get caught with her panties and bra in my pocket. I raced home went to my room and pulled my prize from my pocket. I was as hard as ever. Taking the newly acquired garments from my pocket i was able to examine more closely. I was taken by the aroma emulating from them and brought the panties and smelled them. I got my very first whiff of pussy. My tongue touched the crotch and I tasted what i could from them. This was a real prize and I put them in a secret hiding spot. Later that night I took them out and masturbated smelling them. It was fantastic and my crush for her grew stronger. I inspected the bra and saw that it was size 34b. That explains the perkiness of her breasts. After months of smelling the panties as I masturbated I one day tried those panties on. I was hooked and have been hooked ever since. I never took another garment from my friend's sister, but was able to score a few others from others. When my older sister went away to college, she was such a pain in the butt. I was happy to see her go. She left clothes behind which I was able to wear whenever i wanted. It was at this time that i wore panties more frequently and tried on her bras, stockings, tights, and other clothing. Unfortunately I did not know that she was somewhat anal retentive and always folded her clothes in a certain way. When she came back for fall break she knew something was up. She probably found some stains in the panties because I did not launder them after I wore them. I now some were put away with a wetspot in them. I was in my glory. I had my prize from a few years earlier and others that I was able to obtain and had pretty much free reign to the clothes my older sister left behind. She came home for the summer and my ability to wear her clothes ended. When she left for the fall of her sophomore year and I was now a senior in high school i was relieved. I could go back to wearing her clothes. She didn't leave as much behind this time and it was clearly things that she did not want or like to wear. I was somewhat disappointed for the panties were not sexy. My desires faded. During the summer after my senior year at high school I had a summer job working in a grocery store. There was another guy working there that was home for the summer. He was a rising senior in college. I never knew this guy before but he was cool. One weekend his parents were away and I was invited over to drink a few beers and smoke some weed. It was just the two of us. After a few beers he pulled out his dad's porn collection and we started watching a porno. I had never seen one before but knew what it was all about. After a while it was impossible not to get excited. We sat on the sofa near each other and drank and commented on the scenes before us. After we got increasingly excited we both were quieter. Then this guy got up to get another a beer and when he came back he sat closer to me. I was hard. He was hard. There was no denying it. He reached over and started rubbing my knee. I didn't say no and did say yes. His hand moved further up my leg to where he was rubbing my upper thigh. It did feel good. Then he moved his hand further up and felt my hardness. I moaned and did not discourage him. I put my hand on his thigh and we both moaned. Where was this going? My hormones were raging and i was extremely excited not just from the porno but also from his hand. I knew there was a wet spot in my shorts. Then he stuck his hand in my shorts and felt me. We leaned in and kissed it was magic. That first night we made out and jerked each other off. The next time we got together he took me in his mouth and finished me with his hand. I jerked him off. It wasn't until our 4th time together that I took him into my mouth. I so wanted this and it felt very natural. I enjoyed it and just before he came in my mouth i pulled him off and let him shoot on my face. He licked his cum from my face. The next time he came in my mouth. Then it was time for me to go away for college and for him to return to his. It wasn't until 3 months later at thanksgiving break that we saw each other again. We kept in touch through the social media and texting and knew we had to get together again. We did, but this time was different. I wanted him in me. I wanted him to fuck me and he did. It hurt at first. It was a pain in the butt, but a good pain. It still feels good. College came and went. I had relationships with both girls and guys but more so with girls. After college I started a relationship with Julie. She was the same age and we went to the same school but did not know each other very well. She always wore the nicest lingerie and I made sure to compliment her on it. One night we were getting hot and bothered. She was wearing a skirt and blouse and i had khaki pants and shirt on. She was aggressor this time. When we got to her apartment it did not take long for her to take my pants off. I was sitting on a couch with my shirt still on and briefs. She was full dressed. She was on her knees rubbing my legs and my penis through my briefs. Then in one fell swoop my briefs were off. I was hard. She stood up, reached under her skirt and lowered her panties. Oh my god I thought this is going fast. She stepped out of the panties brought them down to my feet and said "put these on". I could not believe it. Did she really want me to wear her panties? I stood up and she raised her panties up my legs. I could feel the heat and wetness she left in the panties on my balls when they got that high. My penis was straining to get out. She sucked me off. The next time we were together she had a small gift to give me. It was a very flat box and told her she shouldn't have done that. The box was held together with a bow. Slowly I opened it for I had no idea what could be in it. It wasn't thick enough for a book and not big enough for a shirt. What could it be? When it was open i saw not one, but three pairs of panties in different colors. My face immediately went flush and i was a bit embarrassed. "Based on how much you liked wearing my panties I thought you needed some for yourself". Then she said, "In the future when we get together you must wear a pair of panties." And I did. Over the weeks, I started wearing panties even when I was not on a date with Julie. They felt terrific to wear. I liked how they felt. So soft, so thing and not binding. The right cut made it easy for me to fit into them. Julie bought me a few more pairs and then when night she wanted me to wear a bra. Again I was embarrassed but did not put up too much resistance. I wore bras more and more frequently around her and other lingerie. She liked it. I loved it. Did she know of my past. When we slept together i was started sleeping in a nightie and panties or cami and panties. We were now together 7 months she bought me a pair of ladies jeans and a somewhat not too feminine blouse. The fit perfectly. There was more and more feminine clothes, which was okay. One weekend Julie had my come over early on a saturday before we went to meet friends for diner. Little did I know what was in store. As soon I got there she had my shower and shave my legs and face very closely. Once I was almost hair free Julie trimmed my pubic area by narrowing the extent of the path of hair to my penis. She had my clothes for the evening out. It consisted of white stockings, white high cut panties, white demi bra, white blouse and red skirt. I put the the panties and bra on and then she painted my toenails and my fingernails bright read to match the skirt. Was I really going to dress as a woman and go out as one? She did my makeup and told me to finish getting dressed. Which I did with her help. Then she put a wig on my head. I had never worn one before. She got dressed and wore a white blouse and black slacks. Very classy. Her makeup was light and her fingernails matched mine. The last item was a necklace around my neck that hung low and in the opening of my blouse. We didn't meet up with her friends but went for dinner and then to a club to dance. My feet were killing me. Fortunately I was wearing flats and not heals otherwise I am sure there would have been pain. At 1 am we caught a taxi back to her place and as soon as we were in the door she pinned me against the door and kissed and groped me. It was clear that she was going to be the aggressor tonight which was fine since I was enjoying me evening as a woman. She quickly removed my blouse, skirts, shoes but made me leave the stockings, bra and panties on. She undressed to her panties. We made out and felt each other. I like feeling her hands on my "breasts" and rubbing my "clitty" in my panties. I like feeling the heat and wetness she was generating between her legs. I moved down to kiss, lick and suck on her nipples and she started going crazy. I knew she loved having her nipples stimulated for it only made her wetter and wetter. She pushed my head down lower. Her panties were soaked. I licked her through them and sucked her juices from them. I then removed those panties and licked her to 3 very rapid orgasms. Instead of being spent she got up and went the bathroom. When she walked out of the room she had 8 inches of meat attached to her waist. I did not know she had a strapon. She walked closer to me and said "Such my cock my love." I got on my knees wearing panties, bra and stockings and sucked her plastic toy. She kept telling me how good i looked with my painted face sucking her cock. Then she started to slowly started to fuck my mouth. It felt so good. After a while my mouth was getting sore she pulled out and pushed me onto the bed. She removed my panties and my hardness sprung out. "You like this don't you my little slut?" I replied that I did. She lifted reached from some lube and told me to lift my legs up. Which I did. She lubed my hole and she lubed her toy. "Take it in your hand and guide it inside you" she said. I moaned in anticipation for I wanted her to fuck me. I lined her toy up against my hole and let her push it inside. It hurt a little but not much and she was surprised by how easily it went in and how much I appeared to like it. "Does my little girlfriend liked this toy in her?" she said. All I could do was moan. She then fucked me for the next 20 minutes. As she moved her toy in and out I was dripping and came closer and closer to climaxing. Then i did and shot between us up to her breasts. She pulled out and said "Lick your cum from my breasts." I gladly complied. The next morning I ate her again to multiple orgasms. She then asked if had enjoyed sex with another guy before. I told I had. "So the rumors from college were true" she said. I blushed and told her that I was bisexual. She said that she was too and liked thinking it was a woman she was with the previous night. She had me wear panties and a bra all day. Sometimes it was all i wore. Other times I had a robe on. I went back to my apartment that sunday night so sexually satisfied and relieved she knew of my secret. For the next few months we spent weekends together as two woman. It was a rewarding time for both of us. Then one weekend a friend of her sister was in town to look for a place to live since she had just accepted a job in our city. This woman seemed familiar and when I met her I realized it was Angie. My best friends' older sister from when I was 14. Yikes what are the odds of that? In a few hours and after a couple glasses of wine Julie told Angie that I like to wear lingerie and dress as a woman. In fact she said that I was probably wearing panties right then. Angie said "I don't believe it". Julie then asked me to show her what I was wearing. I was embarrassed for both Julie and I knew I was wearing panties. Julie didn't know which ones I was wearing but when I lowered my jeans they both saw that i was wearing black high cut panties with lots of lace and pretty bow in the front. Angie then asked "You didn't happen to take my black and white panties about 10 years ago did you." I was so embarrassed and looked down. All this time she thought it was her younger brother but only then did she realize it was me. I was caught, but maybe being caught this way was not so bad. Julie then asked me to go get dressed. I went into Julie's bedroom put on a blouse and bra that I had left in the apartment. I also had my jeans on. Angie moved closer to me and kissed me. "I always thought you were cute, but now you look better" she said. I almost orgrasmed right there after hearing that. The three of us went to Julie's bedroom and had sex. After all these years i was able to taste Angie's nectar directly from the source and I gave her two quick orgrasms. Julie was not left alone for she was busy with my penis. After I was very hard Julie told me to fuck Angie. Did I really hear that? I moved up Angie's body still wearing a bra and she guided me into her. The fuck was so much better than I could ever imagine. Angie was vocal and moaned loudly. Julie found a way to way to quiet her down. She sat on Angie's face. It was clear that Angie was also bisexual for she dove right into Julie's pussy. If she wasn't bi she knew what to do. Overtime Julie became more and more interested in real woman and started dating girls. We were drifting apart. I happened upon Angie at lunch one day during the week. I told her that Julie and I were no longer together. Angie and I then started becoming closer and had many lunches together. Then we started dating and she asked about my desires to dress. I told her everything including that i liked to suck a cock. After a year of dating I proposed to her and two years later we were married. At the wedding I wore identical panties and stockings under my suit identical to the ones worn by Angie. Angie likes that I have a feminine side as well as a masculine one. It works for us and now I only wear panties. I will often change when I get home from work and put on a bra stockings and dress. During the weekends I underdress and Angie has spent a small fortune in making sure I have nice clothes to wear. We have a nice collection of toys and she sometimes uses a strapon to do me. She was gorgeous when I was 14 and even more so now. I am so lucky to have such an understanding woman as my wife.