Date: Mon, 27 Jul 2015 12:05:47 -0400 From: Andi Subject: Neighborhood Sissy 02 (Transgender-teen) Disclaimer: My stories contain explicit descriptions of consensual and Non-Consensual sexual activities and are not suitable for reading by anyone under the age of 18, or anyone offended by reading such material. These acts include bisexual activity, cross-dressing and other fetishes and perversions. All characters and events are complete and total fiction and comes from the twisted and perverted mind of a long time cross dresser. All Stories are the property of the Author. Any feedback would be greatly appreciated. Thanks. You cam Email me at SissyAndi@safe-Mail.net . Please consider making a donation to the nifty archives so that this great site can remain free and available to all on the Internet. Neighborhood Sissy 002 My name is Eric and I can't believe what has happened to me over the last couple of weeks. I had been caught spying on the neighborhood guys and had been forced to suck several cocks including my two neighbors Ted and his older brother Rick. Ted had even visited me one day and convinced me to let him fuck me in the ass. When Ted had visited me that day he had planted the idea of me wearing my sisters clothes and dressing like a girl while we fooled around. Since that day I had been wearing her panties and had wanted to try more but had been afraid to go through my sisters stuff. Since I had gotten caught spying on the guys that day I had been back to the shed a number of times and one hot afternoon I had sucked off 8 different guys, swallowing most of their loads. I was home alone one Saturday morning when Ted called me asking what I was up to. When I told him nothing and that I was alone he said he was coming over. He said maybe we could have some fun like the last time which I knew meant that he would want to fuck me again. I guess you could say I had a small crush on Teddy, he was 5'10" tall and weighed around 160 pounds. short brown hair and brown eyes. He was slim and in shape but not very muscular. At the time I was only 5'4" and 135 pounds, short blonde hair and blue eyes. Luckily I could wear most of my sisters clothes. Yes it hurt the first time we had sex but the pain turned to pleasure before he came in my ass. I had been fantasizing about getting fucked when I jacked off late at night and I definitely wanted to try it again but I was embarrassed and I would not be the one to bring it up. I decided I would take a quick shower before Ted came over. When I emerged from the shower I started to put my shorts and a T-shirt back on then I got a naughty idea. I quickly went to Stacy's room. I wanted to wear panties for Ted and decided that I should wear clean ones and not the ones I had been stealing from the dirty clothes. It was the first time I went to Stacy's room and went through her stuff. I was always tempted but was to chicken to do it but "having a date" with Ted gave me the courage to go through her underwear drawer. What I found surprised me. I knew my sister was hot and figured that she was having sex with her boyfriend but I never knew she had such sexy lingerie. I found a red lacy bra,panty and garter belt set, I was already hard when I got back to my room to put them on. I thought to myself that I wanted Ted to be happy with the little surprise I had in store for him. I quickly called Ted and told him to give me 20 minutes then come over and to not even knock, I was alone in the house and I would leave the back door unlocked and for him to just come up to my room, I would be waiting on him. I had been watching porn and "how to cross dress" videos on the Internet so I knew how to hook the bra in front and slide it around. I also knew how to put the garter belt on and attach the stockings to the garters and to do that before I put the panties on last. After I had every thing on including the smokey black stockings I could not help but squeeze the head of my cock as I fixed the panties into place and adjust them for the small but growing erection that I had. I had only worn panties before so when I put the bra on I was disappointed that the cups were not filled out. So I used a pair of old socks to pad my bra. I caught a glimpse of myself in the mirror and thought that while I was not knock out gorgeous that I looked sexy. I just wished that my hair was longer. After I was dressed I laid down on my bed and tried different positions trying to decide how I wanted to pose for Teddy. I could not believe I was doing what I was doing, I was dressed like a slut and waiting for the neighbor to come over and fuck me. I was so ready to cum but wanted to wait until Teddy arrived. I tried to be a good girl but I caught myself running my hands up and down my hose encased legs and squeezing the head of my cock. I jerked my hand away and my heart skipped a beat when I heard a knock at my bedroom door. I relaxed a little when I heard Teddy's voice asking if it was ok to come in. I positioned myself in what I hoped was my sexiest pose and told Ted come in. I thought I was going to surprise Ted but I was the one that was surprised because Ted was not alone. He was with a guy that I did not know. They laughed at me when I reached for the sheet to cover myself up. Ted introduced the other guy as Trent, and went on to explain that he had been one of the originals who started the fun in the shed next door but now that he was a sophomore in college he had not been over in a while. Trent was in town and wanted to have some fun before he had to go back to college and was disappointed when he dropped by and no one was in the shed playing. Ted had told Trent that I might be willing to provide a service for them but he was even shocked to see how eager I was for cock. I looked Trent up and down, he was cute. Just over 6 feet tall and 180 pounds. a slightly muscled upper body and a noticeable bulge growing in his jeans. Trent reached out and pulled the sheet off of me and then complimented me on my outfit. And before I could protest they both were running their hands over my mostly naked body. Ted pulled me off of the bed and I landed on my knees. I was kneeling before them and as I looked up They both were unsnapping their jeans and pulling down their zippers. Teddy put his hand in my hair and pulled my face to his cock. I knew what he wanted and to be honest I wanted it too. I opened my mouth and took his cock past my lips. Out of the corner of my eye I seen Ted reach over to slowly stroke Trent's cock. Ted's cock was not small but it was kind of thin. Trent's cock was about 7 1/2 inches long but OMG it was thick. After sucking on Teddy's cock for a few minutes he passed me over to Trent and I took his cock into my mouth. I had to stretch to get the mushroom shaped head passed my lips and I wondered how much it would hurt if Trent decided he wanted to fuck me. I tried not to dwell on how bad the would be for the time being and tried to do a good job sucking Trent's cock. While I was sucking Trent, Ted took my hand and placed it on his cock. I sucked Trent for several minutes then switched back to Ted's cock. I was going back and forth sucking one while stroking the other. Finally Ted just sat down on the bed and pulled my mouth down into his lap. I took the whole length of his cock into my mouth and throat. His pubic hair was tickling my nose as he fucked my mouth. He held my head in place as he shot jet after jet of white hot cum into my mouth. I swallowed as fast as I could but when there was so much cum that it ran out of the corner of my mouth. As soon as Ted's cock started going soft I moved to Trent's cock. It only took a couple of minutes before he came and I was swallowing my second load of cum for the day. After I had swallowed both of their loads I was afraid they were done and that I was not going to get fucked. Trent sat in my computer chair and told me to get up onto the bed on all fours. I was eager to get fucked so I quickly complied. Trent told Teddy that he wanted to watch us fool around while he rested and recharged. I thought Teddy was going to just fuck me but after he joined me on the bed Trent told Teddy to get me ready for his cock. Teddy quickly pulled my panties down and off. When he spread my ass cheeks I was prepared to feel his cock enter me. I was surprised when he started licking my butt and teasing it with his tongue. I gasped when he pushed the tip of his tongue past my anal ring. Teddy started rimming my ass with his tongue and while he did that he reached around and started stroking my small cock. When Teddy started basically fucking me with his tongue I came hard shooting cum all over Teddy's hand and the bed. When I had finished cumming Teddy took the cum he had caught in his hand and started working it into my ass with his fingers. Before he was done he had worked 3 fingers into me. Trent was rock hard now and he climbed onto the bed pushing Ted out of the way. I took a deep breath and readied myself. Even knowing what was coming it was a shock when he forced the big head of his cock passed my anal ring. He grunted as he shoved the entire length of his cock into me. Good thing I was stretched and well lubed or I would have pasted out from the pain. I was begging him to go slow and to be gentle but Trent could not care less about my feelings, he was wanting to cum again and he was using my body to do it. He was making me feel like a cheap whore. Trent was fucking me hard and rough and I was starting to love it. As he drove into me he would grunt and I would let out a squeal like a little girl. As he fucked me he started slapping my ass calling me dirty names. I was not shocked when I realized that it turned me on even more and I was hard again. Actually I had never gone completely soft. As Trent was thrusting forward I started pushing back to meet his thrusts. I wanted his cock as deep inside of me as it could get. Before it was over I had switched from begging him to quit to begging Trent to fuck me deeper and harder. I had turned into a real slut and I did not care all I wanted was to be fucked. While Trent continued to fuck me Teddy moved to the head of the bed and I took his cock back into my mouth and sucked him back to full erection. Teddy said he did not want to cum in my mouth again and pulled out to let his cock settle down. I leaned forward to kiss and start licking his balls. Soon Trent grabbed me by the hips and pulled me back hard driving his cock even deeper than before and held it there. He filled my ass with a hot load of cum. I felt empty when he pulled his cock from my ass. Trent moved around and sat at the head of the bed with his back against the head board. He pulled my head down and told me to clean his cock. It was disturbing to me that I did not find the taste unpleasant. I was kissing and sucking his balls, running my tongue up and down the length of his shaft. While I was cleaning Trent's cock Teddy got behind me and took his turn using my well fucked ass. After taking Trent's thick cock I barely felt Teddy's but he seemed to be enjoying fucking me because he kept telling me how tight and hot my ass was. I was swirling my tongue around the head of Trent's cock when Teddy added his load to Trent's in my ass. All the attention I had paid to tents cock while I was cleaning it got him hard again. When Teddy pulled out Trent took his second turn fucking me and this time he lasted a lot longer. He fucked me long and hard and before he was through I came a second time. This time I came without even touching my cock. I had been well fucked and I laid there exhausted and covered in sweat as I watched them dress. They both thanked me for a great time before they left. All I wanted was to take a nap but knew I needed to wash my Sisters lingerie so it could dry and I could put them back in their place before she came home. While I was waiting for the clothes to dry I took a shower. As I soaped up my body I realized that my ass was sore from the hard fucking that had taking place. As the water ran over my naked body I reached behind me and started working a soapy finger into my but trying to ease the pain. I stroked my small cock as I fingered my stretched ass. As I played with my cock and ass I fantasized about being group fucked by not just two but a large group of guys. The boys taking me one after the other. I came again in the shower. That night I wore a fresh pair of lacy pink panties to bed. I was on the verge of falling into a deep sleep when the phone rang and I answered it. It was Trent. He thanked me again for a great time and surprised me when he said he wanted to see me again before he headed back to college. Trent was actually asking me out on a date. I had no idea how we were going to make it work but being the slut I had become of course I said yes. ******** To be continued......