tagTranssexuals & CrossdressersHigh School Friend Has A Secret Ch. 02

High School Friend Has A Secret Ch. 02


It had been a little over a month since my first transsexual encounter and it still felt like it was yesterday. My night with Michelle had been a night of many firsts for me but I regretted nothing about it, only that I had to hide it from my girlfriend. I wasn't the cheating type and it did bother me to a certain extent that I was keeping this from Brittany. I was more worried that she'd be grossed out than anything. But after a month of keeping it from her I felt it was time to spill the beans and fess up.

It was spring break and instead of staying in my crappy apartment I decided to spend it at Brittany's house. It was a small but very nice house and she lived there with one roommate, Katie. Katie was one of Brittany's oldest friends; I believe they've known each other since before first grade. She was a very attractive girl; about 5'6, long brown hair, lightly tanned skin and nice C cup tits. Her mom was beautiful in her hay-day, she used to look like Elizabeth Hurley when she was younger, and Katie shared a lot of her mom's best qualities. She was a very sweet girl as well, always soft spoken and very friendly.

When I got back to Brittany's house Katie and her were relaxing in front of the T.V. as they normally were. After I greeted them both I set my things down in Brittany's room and decided it was time to tell her, no more waiting. I told her we needed to talk and she gave me a confused and worried look; I felt awful.

"Well there's no easy way to say this but I guess I'll start at the beginning, Michelle.... she's a transsexual," I told her trying not to make eye contact.

She stared at me for a second, with an awkward look on her face and said, "I know..... but why would she tell you?"

"What do you mean you know?!?" I said in instant surprise.

"I mean I already knew... my mom has been helping pay for her surgeries, (Brittany's parents were extremely rich) but how do you know that she is a transsexual?"

"Well...." It was now or never, I had to finally fess up, "she came over to my place about a month ago and we had sex, I hope you don't hate me forever, I didn't plan for it to happen it just did. She found your strap on in the closest and one thin led to another. I'm so sorry." To my surprise she didn't instantly freak out like I thought she would, she just sat there for a few seconds, speechless.

"Well I guess it could be worse," she finally said after a long pause.

"What? You're not going to freak out or break up with me?" I said in complete shock.

"Well no... its not like you're going to break up with me and marry a transsexual... at least this way I know it's just sexual," she told me. I was completely amazed by her outcome. As my mind processed what she was saying it began making some sort of sense to me. I certainly had no intention of marrying a transsexual, I wanted a family later in life; my affinity for transsexuals was simply lust.

"So you're not going to break up with me?" I asked still a little confused.

"No I'm not going to break up with you.... but how about next time you call me and I'll come over to join you," I nearly creamed myself right there. This conversation had already been one of the most shocking moments of my life and it just got even crazier.

I nearly choked as I said, "so you want to have a threesome with Michelle and me?"

"Well I'd rather be a part of it, if you enjoy doing it then I want to be there with you, I just don't want to be excluded," she explained. "And it doesn't necessarily have to be Michelle, it can be any tranny."

"Don't tell me you know more than one..." I said completely amazed.

"Well yea... Katie is a transsexual too, my mom began helping her get through the surgeries a long time ago and I met Michelle through Katie," she explained. While it made some sort of sense I was still completely in shock. This conversation had gone from me thinking I was going to get dumped to my girlfriend revealing another one of her friends as a transsexual. Brittany and I talked for a bit longer, she told me that she'd tell Katie that I knew she was a tranny, and she eventually got more of the details about my night with Michelle. If it wasn't mistaken I'd say that she was turned on by it...

Surprisingly it wasn't awkward being around Katie. I thought she would be weird or nervous about me knowing her secret but she acted completely normal. Eventually I worked up the courage to ask her about it and she told me how she and Michelle had been friends and how she introduced her to my girlfriend. Everything was starting to make more and more sense.

Spring break moved by slowly until Brittany's aunt called one night. Turns out her aunt had a business emergency and she asked Brittany to baby-sit her two kids while she was out of town for a day or two. Brittany and her aunt were very close so she told her aunt she would help. I was a little bummed out that Brittany was going to have to leave for a couple nights. I though about having her ask her aunt if I could stay over too but I decided it might be inappropriate. She probably didn't want two horny teenagers in a house alone with her kids, pretty understandable. Around 9 that night she left to head over to her aunt's house, leaving me and Katie alone in the living room.

"That sucks Brittany had to leave at the last second to help out her aunt," Katie said; I could tell she was trying to make conversation.

"Yea, this isn't the first time this has happened though, her aunt asks for her help a lot," I replied. The two of us sat together watching movies on Hbo and Cinemax for about 30 minutes before I began to feel comfortable around Katie. I still felt a little awkward knowing such a big secret about her but she had been very easygoing when we walked about it before and she did her best to lighten the mood. We continued chatting and both began getting a little more settled in as the night went on. It was about an hour and a half after Brittany left that she dropped the first bomb of the night...

"So how was your night with Michelle?" she asked with a smile on her face.

I nearly choked when she said it but replied in shock, "who told you about that??"

"Michelle and Brittany both told me. You honestly didn't think someone wouldn't tell me did you? I've known Brittany and Michelle forever."

"Well I guess I didn't really think about it, they haven't told anyone else have they?" I asked, fear racing through me.

"No, no no, don't worry about that, I know neither of them would ever tell anyone about it, and neither would I; you've got nothing to worry about."

"Wow... you scared the hell out of me for a second their, I thought Michelle had told everyone she knew."

"No she wouldn't do that.... But really.... How was it?" she asked again.

"Your really want to hear about it? I thought you said Michelle already told you about it?"

"Well yea she told me that she loved it, but I haven't heard if you likeed it or not. I want to here your side of the story," she explained.

I finally gave in and gave her every little detail. I told her about how Michelle found Brittany's strap on and how nervous I was when Michelle was about to shove her 8 inches of meat inside me. Katie never broke eye contact with me as I went on and on about our night. As Katie continued to listen I could tell she was getting aroused. I looked down at her thigh and noticed her hand slowly massaging up and down her leg, moving closer and closer to her groin. She was trying to be discrete about it but I knew she was getting turned on by every little detail.

"So I guess its safe to say that you loved your tranny experience?" she asked with a large grin on her face.

"Yea defiantly, and Michelle said she wanted to meet up again but unfortunately she's a thousand miles away in New York," I told her.

"Well she may be in New York but I'm here," she said as she stared into my eyes.

It took me a second to realize what she actually said but when I did I knew exactly what she meant. I didn't say anything as we sat on the couch together staring at each other for a few seconds until she leaned over towards me and starting kissing me. I instantly began kissing back and pulled her down on top of me as we continued making out. I brushed her long brown hair to the side as we passionately kissed for what seemed like forever. She finally broke out kiss and sat back up for me to admire her. She was wearing a tight white t-shirt and short sleeping shorts that barley made their way past her package. I leaned up towards her and pulled her shirt over her head, exposing her black bra and beautiful breasts. I instantly un-strapped her bra moved toward her chest and began kissing and massaging her tits. She moaned in delight as I flicked my tongue across her raging hard nipples. Before I could finish she leaned onto her back and slowly slid her cotton shorts off, exposing her satin black thong. I tried to make my way down to her groin but she pushed me onto my back and began to strip me down.

She ripped my shirt and jeans off like they were on fire and then my boxers with the same fury. Before I could do anything else she had started for my cock. She took me in her mouth and slowly began working her way up and down my shaft. It took mere seconds before I was rock hard. She was now in the doggy style position as she furiously sucked me off. I glanced around at her beautiful ass that was arched up into the air and I couldn't wait any long to start fucking her little ass. "Stop, stop," I begged as I could fell myself getting close to cumming.

"What, is something wrong?" she asked with a worried look on her face.

"No, everything is amazing, wait right here," I instructed her. I quickly ran into the bedroom to grab some lube and headed back to the living room. When I got back Katie was lying in virtually the same position, now with her stomach flat against the couch with her beautiful ass staring me right in the face. I moved over to the couch and pulled her legs apart, exposing her black thong. She instinctively moved up onto all fours as I began kissing her gorgeous ass. I slowly planted small kisses all over her ass cheeks. As I moved closer to her asshole I could tell she was becoming more and more horney. I finally pulled her thong aside and began passionately eating out her ass. The second my tongue touched her asshole she let out a load moan and it didn't stop. She groaned loudly as my tongue began to loosen her tight asshole. I flicked my tongue across her hole countless time and began driving my tongue against her sphincter. Slowly she began to relax as I continued to tongue her ass.

After a few minutes I could tell she was ready for me. "Have you ever done this before?" I asked before proceeding.

"Yea but just a few times, you'll have to be gentle," she replied with her ass still beautifully propped up in the air.

"I will be, don't worry," I assured her. I reached for the lube and graciously covered my cock and applied a large glob to her asshole. With my cock now ready I positioned myself behind her and slowly moved her thong aside. Carefully pushing my cock against her ass I could hear her moan as the pressure against her asshole increased. To my surprise my cock pushed past her sphincter but not without a loud yelp from Katie.

"You okay?" I asked with only a couple inches of my cock buried in her ass.

"Yea just give me a second or two, you've got by far the largest cock I've had inside me." I let my cock rest inside her ass for a minute or to until she finally began pushing herself back against my groin. I nearly came right there as she pushed her ass against my dick. I watched in awe as all 7 inches of my cock slowly disappeared into her asshole. Once all of my meat was inside her she rested again for a second or two until her ass had become accustomed to my cock. After she had relaxed a bit more I began slowly pushing my cock in and out of her tight ass. She moaned in delight as my dick steadily glided in and out of her. I leaned town towards her shoulders and pulled her hair, pulling her face back towards mine. I furiously kissed her as I quickened my pace, now rapidly pumping in and out of her. She began moaning loudly in the middle of our kiss; I was so turned on by the fact that she couldn't even kiss me without losing control of her moaning.

I continued picking up the pace and grabbed her ass to hold on. I loved it when girls kept on their panties while I fucked them and Katie's ass looked amazing in her black satin thong. It was still pulled to the side, racing across one of her ass cheeks, exposing her asshole to my cock. I looked down to watch my raging cock as it thrusted in and out of her perfect ass. She was still on all fours, moaning so loud I thought the neighbors would hear us as I continued to pound her rear.

After what seemed like forever I slowed my pace and pulled my cock from her asshole. I quickly grabbed her ankles and rolled her over onto her back. I looked down and saw her large package staring me right in the face. I had gotten so caught up in fucking her ass I almost forgot about her little secret; Kaite was so hot though that it was very easy to forget that she wasn't a normal woman. Before I could reach for her cock she grabbed my dick and pulled it back towards her asshole. I could tell she wanted me back inside her and of course, I granted her wish.

My cock easily slid past her asshole this time; I had already given her ass a long pounding. She began moaning again just as before but this time I wasn't going to ignore her cock. While I was still thrusting in and out of her ass I reached for her black panties. I could see she was already extremely hard as her cock was shoving itself against her thong, begging to be released. Slowly pulling them aside I finally exposed her rock hard dick. She wasn't as big as Michelle but still a very impressive 6 to 7 inches or so. I was certainly relieved to see she wasn't any bigger than Michelle, I was pretty sure I couldn't take anything bigger than Michelle's monstrous cock.

With her cock finally released I began jacking her off in rhythm with my thrusting. As my dick slammed in and out of her tight ass my hand moved furiously up and down her shaft. She began grabbing at her breasts as she groaned in delight. Eventually I took my hand from her cock and pushed her thighs up against her chest. Leaning forward I began kissing her again as I continued to pump in and out of her. As we kissed I could hear my balls slapping against her ass as I buried my cock inside her tight ass. Breaking from our kiss she took control over her cock for me and began jacking herself off as I continued fucking her.

I could feel myself getting closer and closer to cumming as Katie continued jacking herself off. She looked so incredibly gorgeous while I was pumping her tight ass. Her perfect tits were bouncing back and forth and she had her head cocked to the side, her mouth gaped open as she filled the room with her moans. Just as I felt myself getting closer to cumming she began jacking herself off even faster. I tried to hold my load for just a few more minutes to make sure she came along with me. I kept trying to look somewhere else in the room to distract myself from her but my eyes always made their way back to her beautiful body.

"Oh fuck me faster, I'm so close," shed moaned. Her talking dirty to me certainly wasn't going to help me hold my load but I sped up the pace as best as I could. All 7 inches of my cock were rhythmically slamming in and out of her now loose ass. Only a few seconds after I sped up she began moaning even louder.

"Ohhhhhhhhh...... Ohhhhhhhhhh..... Ohhhhhhh....." she finally let out a loud shriek and began cumming all over her chest as she jacked herself off while I continued fucking her ass. Glob after glob of cum covered her stomach, thong and tits; I didn't think her cock would ever stop cumming. Seeing Katie's cock cover her tits with cum was finally enough to send me over the edge.

"Ohhh Katie I'm going to cum," I screamed out in pleasure.

"Cum inside me," she moaned to my compete surprise, but she certainly didn't have to tell me twice. I felt my cock grow a bit more inside her ass as I came closer and closer to filling her ass with cum. The sensation her ass was giving me cock only intensified as I finally started cumming in Katie's perfect ass. Just as I came I moaned on the top of my lungs and I noticed Katie giving me a sly grin. I felt my cum fill her ass as I sent load after load into her ass. I continued pumping in and out of her as my cum lubed up her ass even more. I looked down to see my cum slowly ooze out of her ass as I finally slowed my pace.

After my cock finally stopped I let it rest inside her ass for a second or two before finally withdrawing it. More cum continued to ooze out of her as my cock popped out of her. I tired to continue admiring the pounding that I had just given her asshole but she pulled my face down to hers and planted a long kiss on me. I felt her cum covered tits brush up against my chest as she pulled me on top of her.

"That was incredible," she cooed after she finally broke our kiss.

"Ditto," was all I could get out of my mouth as I was still panting and trying to catch my breath. I pulled myself off Katie and made my way to the bathroom to clean up. I was never much for "cuddle-time"; not to mention we were now both covered in her cum. She made her way into the bathroom a few seconds after me and gave me a smile and my ass a smack as she walked by. It had been an amazing night but all I could think about was the fact that we still had one more night alone.

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