tagTranssexuals & CrossdressersHigh School Friend Has A Secret

High School Friend Has A Secret

byhorneyguy99©

I had just walked inside my apartment after a 10 minute walk from the grocery store in the blistering cold. It was a frigid Denver day in the middle of February, the kind that forces you to sit cooped up inside all day. My roommates were still back in our hometown visiting old friends and family. We had all come to Denver 2 years ago to attend college and as sophomores, we were loving every minute of it. The day had moved along very ordinarily until I received the strangest phone call. My girlfriend's best friend from high school was calling me. I had known here since freshman year and we hung out fairly often, her being my girlfriend's best friend and all, but she had never called me. I curiously picked up my cell and answered, "Hello?"

Turns out she was back in town visiting her family and was on her way back to New York City. She had a 6 p.m. flight but it was cancelled due to the heavy snow. Apparently she got into a big fight with her parents about school and had no intention of going home. We talked for a little while and then she asked, "Well things aren't working well for me at home and all the hotels around the airport are full so do you think I could crash at your apartment?" I was hesitant at first because my girlfriend was the extremely jealous type, I told Michelle she could stay over but could tell absolutely no one, especially not my girlfriend. She agreed and grabbed a cab to head to my apartment.

About 30 minutes after I had hung up my cell I heard the knock at the door. When I opened it I saw her; I hadn't seen her since the summer after senior year of high school and I quickly noticed that she'd changed greatly for the better. In high school she was certainly attractive but had a few minor flaws. She had huge D tits and a great round ass from her years of dancing but she was about 10 pounds too heavy and her skin was a tad too pale. But when she walked into my apartment she had corrected all her previous flaws and looked amazing. She looked as thin as a model, her skin looked much tanner, and she hadn't lost her great tits or ass.

"Hey you," she said with a smile as I opened the door. She quickly gave me a hug as I helped her get her luggage inside.

"Wow you look great," I told her as she walked into my living room.

"Thanks, you don't look too bad yourself," she replied with a grin.

We used to flirt a fair bit when my girlfriend wasn't around back in high school but nothing serious ever came of it, just a bit of fun as we saw it. Once she got her heavy coat of I noticed she was wearing a tight black collared shirt which looked like it was strangling her massive tits. My gaze trailed down from her tits to her tight blue jeans that beautifully extenuated her nice ass. As she sat down on my couch I could feel myself getting a minor hard on, her long red hair seemed strangely exotic to me as she was probably the only hot red head I'd ever seen. I sat down on the coach with her and we watched some T.V. and caught up about school and our lives.

After about an hour of talking and laughing she yawned and said, "I'm getting a little tired, how about you show me to your room." I had decided to be the gentleman and let her sleep in my bed while I took the couch in the living room. I walked her to my room and helped her get settled in. She unpacked a few of her things as we continued to reminisce about our senior year of high school but things were about to take a very interesting turn.

I was sitting on my bed watching T.V. as she was searching around in my closet. She had found some old boxes of pictures and graduation stuff and was having a ball making fun me and all my old friends. I could hear her shuffling around in my closet and then heard her say with shock, "Oh my god what is this?" I looked over in horror and saw her holding my girlfriend's strap on dildo.

Me and my girlfriend were very sexually adventurous and tried just about everything you could thing of. After about 2 years of dating, I drunkenly asked her, "How would you like to use a strapon on me?" To my amazement she instantly said yes and she has been pounding my ass ever since.

Back to Michelle though..., I could do nothing but just stare at her with my mouth wide open. Strap on in hand she walked out of my closet and sat down on the bed with me, a huge grin on her face. "So...... care to explain?" she said with a giggle.

I didn't even try to bullshit her at this point, maybe if I came up with a great excuse the second she brought it out I maybe could have gotten away with it by my hesitation and facial expression gave me away. "Yea......" I muttered as she sat next to me, strap on still in hand. I had no idea what to say, I had been caught red handed and it was quickly becoming one of the most awkward situations of my life. I couldn't say anything.

"Well if you're not going to answer I'll take a stab at it for you," she said. "I'm guessing you and Brittney get drunk and horny and she fucks you in the ass with this, am I right?"

Mortified I finally gave in, "Yea that's pretty much dead on," I said, trying to avoid eye contact.

But what she said next completely shocked the hell out of me. "Don't be ashamed of it," she said as she placed her hand on my thigh. "I think it's hot that you'll think outside the box and just do whatever feels good," she said with a sly grin on her face. I made eye contact for the first time in minutes and she was staring straight into my eyes. "In fact," she said, "I have a bit of a surprise for you that might be just up your alley."

"I have something I want to tell you but you have to swear you won't tell anyone," she said as she shifted herself towards me.

"Well you know a pretty huge secret about me too so I don't think I'll be telling anyone about any of this, ever," I laughed.

She giggled and moved herself off the bed and stood directly in front of my as I sat on the bed. "You promise right?" she said one last time.

"Yes, tell me already!" I exclaimed, I was getting a little intrigued by now and just wanted her to get on with it.

"Ok.....," she said with a shy look on her face, "You have to promise not to think I'm weird or kick me out of your apartment or anything like that."

"I promise just tell me!"

"I'm a transsexual," she quietly said.

"A what???"

"I knew you wouldn't understand," she said as she sat down on the bed next to me.

"No no no," I pleaded, "I didn't mean it to come out like that, I'm just a little confused."

"I have the body of a woman but I have a penis," she told me as she stared at the floor.

We talked about it for about 15 minutes. How she struggled in high school with boyfriends; now I knew why she would never let any guy go down on her. She told me how she was saving up to get the final surgery but it could still take years. After she calmed down I asked, "Why'd you tell me this?"

"Well I thought since you're open sexually to different stuff that you might....." she paused, "..... That you might want to have sex with me. I've never had sex with anyone and I don't want to risk getting a disease by going to a transsexual bar and picking up a stranger." She paused again, "but if you think its gross and don't want to or you want me to leave I completely understand," I could tell she was getting a bit nervous now.

"No, no, no" I said as I tried to comfort her. I was still trying to grasp the situation but I could tell that she'd probably never revealed this to a guy before. She was still sitting next to me with her head down as I gently lifted her chin and told her, "sure, I'll try it with you since you're a virgin."

She didn't miss a beat as she wiped her watery eyes and gave me a huge hug. She furiously started kissing up and down my neck. She moved up my neck and planted a huge kiss on my lips. Amazed by her enthusiasm I could feel myself getting hard quick. Still kissing me she reached down to my jeans and began massaging my package. She continued to work my bulge until she broke our kiss and, while giving me a huge grin, began unzipping me jeans. She pushed me down onto my back and yanked my jeans and boxers off in one motion and quickly moved down to my now hard shaft. With her mouth as wide as it could go she started sucking up and down on my cock. She wasn't too bad for her first time and it was very sloppy, which I loved. She kept moving bobbing up and down on my 7 inch fully erect cock and I started to get close to cumming after only a few minutes. "Ok Ok," I said as I pulled her head of my cock before I came too soon, "We've gotta save that," I told her with a smile. She smiled right back and moved down to my balls. She began slowly tonguing them and quickly worked her way up to a hard sucking. She moved from ball to ball, taking each on entirely in her mouth.

Without any warning she grabbed my legs by the thigh and pushed them back to my chest. I was now on my back with my legs pressed up against my chest with her kissing the tender area around my scrotum. She teased me, slowly kissing all around my ass and then to my surprised, dove right into my tight asshole. It had been a long time since my girlfriend had tossed my salad but Michelle quickly revived my passion for it. It felt amazing as she pushed her tongue against my sphincter as hard as she could. I could feel it loosening up and she knew it too. She slowly moved her hand down to my eager ass, still pushing my legs to my chest, and began pushing on my asshole with her index finger. It felt amazing as she slowly worked her finger into my ass. She moved her mouth back up to my balls as she began finger fucking my ass. After about a minute she slid her middle finger past my sphincter which began to really stretch my ass for the first time that night.

After a few minutes of her pounding my ass with her fingers I pulled her face up to mine and gave her a long sloppy kiss. She pulled my shirt off over my head and moved off the bed. Standing about a foot away from the bed she motioned me over to her. She planted another hard kiss on me and then pushed my head down to her crotch. I crouched down on both knees with my face staring directly at her crotch. I slowly unbuttoned her jeans and carefully pulled them down to the floor. As they fell to the ground they exposed her small black cotton thong..... along with her huge bulge. I knew right when I saw her cock trapped inside her small panties that she was huge. I started to tease her just as she teased me, slowly kissing around her package, occasionally planting a big kiss right on her bulging cock hidden beneath her panties.

"Please suck me off," she moaned, "no more teasing, I want to know what it feels like."

I quickly obliged and finally revealed her massive member. Moving her thong to the side her huge cock popped out and smacked me on the cheek. She giggled and then grabbed her shaft and guided her head into my open mouth. I could barley get my mouth around her growing dick as I began to suck her off. I had sucked on my girlfriend's strap ons only a few times but it was nothing like the real thing. I could hear her begin to moan as I slid my mouth back and fourth on her raging cock. As I continued sucking her dick it kept growing and growing. After about 2 minutes of sucking away on her cock she had a full hard on. When I pulled her dick out of my mouth I quickly noticed it was bigger than my own cock. It felt a little strange; this tiny 5 foot 3 100 pound red head had D tits, a great ass, and a cock longer than mine.

"Wow...." I said amazed, "how big is that thing?"

"8 inches," she said with a giant smile on her face.

Before I could get another word in she grabbed my head shoved her dick back into my mouth. This time she held my head still and began to fuck my mouth with her long shaft. I held on to her thighs for dear life as she slammed her cock against the back of my throat. After a few more minutes of sucking her off, I stood up and guided her back over to the bed.

I pushed her backwards onto the bed quickly moved between her legs. I began kissing her again and moved my hand down to her asshole but she stopped me right as fingers reached her sphincter. "I've tried all types of dildos, butt plugs, anything you can think of; but having anything shoved up my ass just doesn't work for me," she told me. I'd heard that some people just never like anal no matter how many times they try it but she did catch me a little off guard. "I'm really sorry," she muttered with a frown on her face.

"Well..... what do you want to do then?" I asked

"I was kind of hoping that I could do you, like how Brittney does with a strap on," she said as I gazed at her huge member.

"Well you're a lot bigger than the slim 6 inch dildo that she uses, but I guess you can give it a try. You'll definitely have to go slow though," I said as I was getting a little nervous about her 8 inch cock stretching my very tight ass. I sometimes had trouble with the 6 inch dildo that Brittney used on me, I had no idea how she was going to ram her huge dick into me.

"OK, I promise I'll go slow," she exclaimed with a smile on her face. She moved her mouth back up to mine and planted a long kiss on me and then moved out from under me.

"Ok get on all fours," she instructed.

I moved up a little further on the bed as I got down on my hands and knees. She walked around the bed and then got on her knees right behind me. She pulled her shirt off over her head and quickly undid her bra and freed her huge tits. She then positioned my ass at the correct height and reached down for her member. I glanced back at her and she looked amazing. She still had her tiny black thong on, just moved to the side with her giant cock sticking out. Her tits were incredible and she caught me staring back at her and gave me a big grin.

"Do you have any condoms?" she asked.

"Yea in the nightstand," I replied.

Still positioned behind me she ripped a Trojan out of the package and slid it down her hard shaft. She smiled as she barley got the condom around her huge member.

"I'm surprised that thing fit you," I laughed.

"Like a glove," she smirked. Once she had the condom on I knew it was time. I bent my head down into the bedspread and prepared for the worst. She grabbed some lube from the nightstand and covered her thick cock. Once lubed up she slowly pushed her cock against my tight sphincter. She took her time, slowly pushing against my tight asshole but not penetrating. After about 2 minutes of her softly rubbing her head against my ass she increased her thrust. With a little more power I felt her cock head pop past my sphincter. That first moment when a dildo or cock pops into your ass is always the most intense. I let out a loud moan as her thick cock penetrated me. My ass felt like it was going to rip in half, she was so much bigger than the dildo I was used to. I reached back and pushed against her stomach to keep any more of her massive cock from sliding in. She knew I was uncomfortable and let about 2 inches of her cock sit in my ass for a minute or two until I got accustomed to it. My ass felt stretched 10 times what it normally did when my girlfriend fucked me. I grabbed my pillow and dug my fingers in as hard as I could as my ass throbbed with pain. After another minute or so I was about to call it a night but the pain began to fade. Slowly the pain began to fade and I was finally getting used to having Michelle's huge cock inside me.

"How does it feel not to be a virgin anymore?" I said back to her.

"It feels great," she smirked, "are you doing ok or do you want me to quit?"

"I'm fine now, you can start fucking me," I begged her.

Without hesitation she began to push more and more of her member inside me. Inch by inch I felt my ass being filled by her huge meat. Just when I thought I was going to explode I felt her balls hit my ass. She'd finally gotten all of her cock inside me and I felt amazing. She took her hands off her dick and grabbed my ass at both cheeks. I glanced over to my right and saw both of us in my mirror. I watched as her huge cock disappeared into my ass as she thrusted into me and reappeared as she pulled out. I began moaning loudly now as my ass was now completely accustomed to her raging cock.

"Oh fuck yea," I heard her moan. Me nor my girlfriend talked much during sex but I was getting turned on by Michelle's enthusiasm. "Oh your ass feels so good," she said as she began to pick up the pace. The warm up was over and she was now slamming her cock in and out of me. She moved her hands up to my shoulders to get a better hold of me as she pounded into my tight ass. She reached forward and pulled my head back to hers. With my head pulled back by my hair she leaned forward and starting tonguing my mouth as she railed my ass. It felt so amazing to have her bury her tongue deep in my mouth as all 8 inches of her cock slid in and out of me.

After about 15 minutes of her fucking me doggy style I asked, "Do you want to try any other positions?" I had forgotten that she was new to this and thought maybe I should take the lead.

"Oh, sure," she said as she pulled her member from my ass.

"Well what do you want to try?" I asked while still on all fours with her huge cock resting against my ass.

"I guess we can try missionary," she smiled back at me. Before I could move an inch she reached down for my ankles and flipped me over onto me back. On my back I watched as she positioned herself between my legs. She pushed my legs against by chest like she had before as I reached down to guide her cock into my eager ass. She leaned down to my mouth and kissed me as she slowly thrust forward. I guided her enormous member towards my ass as it inched forward and pushed against my tight ass again. This time it entered much easier than before but still with about 4 inches popping in all at once; enough to cause me to let out a load moan as Michelle was still kissing me. She smiled as she could tell that her member was stretching me to the limits. It seemed that even transsexuals got the same enjoyment that guys do when they see that their cock is making their partner squeal due to its massive size. Once I got past the initial pain of her entry she started slowly trusting again. I reached down and grabbed both her ass cheeks and helped her pump in an out of me. I caught a glance of her in the mirror again, this time I saw her beautiful ass thrusting forward and back as she pushed me to the limits. She started to pick up the pace as I reached down and started jacking myself off as she pumped away.

"Ohhhhhhhh I'm gonna cum soon," I moaned as I could feel myself getting closer and closer. She didn't say a word but kept her hard cock rhythmically moving in and out of my ass. She kept building up speed and I couldn't take it any more. I started cumming all over my chest and stomach as I experienced one of the most intense orgasms I'd ever felt. Globs of cum kept shooting out of my cock while Michelle leaned down and began to kiss me again. After my cock finally finished she slowed down her thrusting and allowed me and her to catch our breaths. She continued kissing me for minutes while she kept her still hard cock in my ass.

We broke our kiss and she pulled her self out of my ass. I gave her one more kiss and limped over the bathroom to clean myself off. I could barely walk I'd been fucked so hard. I grabbed a towel off the rack and cleaned the load of cum off my chest. It quickly occurred to me as I was cleaning up that Michelle still hadn't came... my work wasn't done yet as I would soon find out. After I'd cleaned up I wandered back into the room to see her beautiful body sprawled out on my bed. She was lying on her back with her legs wide open, slowly massaging her massive tool.

"I guess your not done yet?" I asked with a grin on my face.

"Not yet, and I hope your not either," she replied, returning by grin.

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