tagTranssexuals & CrossdressersHigh School Friend Has A Secret Ch. 05

High School Friend Has A Secret Ch. 05


Spring break was gone now but it was far from a distant memory. My amazing week with Katie and Brittney had been some of the best sexual experiences of my life. I played those nights over and over again in my head for months afterwards. Brittney even seemed to share my passion for our threesome. She constantly reminded me how great it felt to have Katie and me inside her at the same time. She wanted me to come back to her house so we could have a repeat but I never found the time during the rest of my semester. Every week I tried my best to make time for a trip back there but there was something always in the way.

Before I knew it summer had arrived. Finals were coming to a close and I couldn't wait to get back to Brittney and Katie. Once again I was planning ever position out in my head. First, I thought, I want to try sucking Katie off while I fuck Brittney. Then I figured I could try fucking Katie while she ate out Brittney. The possibilities were endless to me. But all my plans went out the window during the last week of class.

"John, come over here for a second," my professor said.

"What is it Dr. Stephens," I asked him.

A big smile crept across his face as he said, "You got the internship!"

I sat there confused for a second, "Wait, which one, Chicago, Dallas, L.A., New York?"

"New York," he exclaimed. "One of my old friends in the company let me know when I told him that you'd applied."

"Wow, that's incredible, when do I leave? Which term is it?"

"The first term, a two week internship, you leave right after school ends," he informed me.

I was so excited I didn't know what to do with myself. I just sat there in awe for a few seconds, thanked my professor and walked out into the hallway. Just as I entered the hallway I felt my stomach drop. I'd just remembered something incredible about New York. I couldn't believe that it took me more than 1 second to put it together but I had just remembered that Michelle lived in New York. It had been so long since I'd last seen her. I had so many questions racing through my head: Would she want to see me? Could she be in a relationship with someone else right now? I fumbled in my pocket for my cell phone and immediately dialed her number. I waited a few excruciating seconds as the phone rang and rang.

"Hey you!" It was Michelle's sweet, soft voice. "What have you been up to?"

I completely ignored her question, "I'm coming to New York in about a week, do you want to hang out?"

"What? You're coming to New York City?" she asked.

"Yes! For an internship, do you want to see me?"

"Wow that's incredible, of course I want to see you. I've been dying to see you again since that night in your apartment. I still think about it all the time."

I instantly sighed a breath of relief. Not only was she free to see me but she seemed just as excited about it as me. "I think about it too. So you're not seeing anyone right now or anything like that?"

"Are you kidding? I haven't been with anyone since I've been with you," she told me.

"I know this may sound selfish but that's exactly what I wanted to here."

She laughed. "No, I've been very single lately. I've wanted to come back home to see all of you guys but there just hasn't been any time."

"I know what you mean, but I can't wait to see you. I think about you and that night we had, I can still remember how sore my ass was for days afterward."

"Yea you took a beating that night. I'd love to give you that feeling all over again," she said with a sly tone.

I could feel my dick growing in my pants as the conversation went on. We talked for a few more minutes. I told her about my nights with Katie and Brittney, she said she was jealous that she wasn't there. We finally wrapped our conversation up and I told her to head to my hotel the second I got into town. She agreed.

While I was extremely excited about my trip to New York, the information came at a bad time. I was in the middle of finals and it was all I could think about. Trying to study while thinking about Michelle pounding me with her huge dick wasn't easy. But I finally made it through finals and was ready for my trip up to New York.

Brittney met me at the airport to see me off. "So, are you gonna call Michelle when you get there?" She asked with a slight smile on her face.

"Yea I was thinking about it, would that be O.K. with you?"

"Go for it, I know how much you enjoyed yourself last time you were with her. Maybe I can make it over there next week and the three of us can get together." Brittney said. Her school ran a week longer than mine so she was still in school during my first week in New York.

"Wow," I told her. "I would love it if you came up, and I'm sure Michelle would too. It's been a while since she's seen you and you two used to be such good friends."

"Yea, I'll see if I can find a decently priced plane ticket. Well you'd better go before you miss your plane. I love you."

"I love you too," I told her. I gave her a long kiss and then headed for my terminal.

A few hours passed and I found myself hailing a cab in New York. My hand was nearly shaking as I reached for my cell once I was in the cab.

"Are you here?" Michelle said as she picked up the phone.

"Yea, I'm in a cab on my way to the hotel, do you want meet me there in an hour?"

"Definitely, I'll call you when I'm in the lobby."

The trip to the hotel took forever. Of course ,the typical Manhattan traffic screwed me. When I finally reached the hotel I checked in and headed for my room. Sitting on the bed I felt like I couldn't do anything. Instead of relaxing and turning the TV on I just sat in silence. My nerves were way too tense and I couldn't calm down. The thought of seeing Michelle again was finally coming to life and I couldn't take it any longer. Just when I thought I was going to go insane my phone rang and it was Michelle. I gave her my room number and she said she'd be up in a second. For what felt like eternity I sat and waited for a knock at my door. When it finally came I nearly fell off the bed in excitement as I raced for the door.

When I opened it I saw Michelle standing in the threshold, she looked just as amazing as I remembered. She was wearing a pair of short, plaid shorts and a tight black t-shirt. The shirt was perfectly accentuating her tits as it looked like it might rip from the tension any second. Her long red hair was straightened and fell just below her shoulders. But before I had more than a second to take her body in she pushed me back into the room and started kissing me. She thrust her tongue into my mouth and all my anxiety was finally gone. I grabbed her ass and lifted her off the ground. She wrapped her legs around my waist as I continued fondling her ass while I held her. She had her hands on my face as she continued to pummel my mouth with her tongue.

When she finally broke our kiss I could do nothing but stare into her eyes, breathing heavy. "Wow, I needed that," she said, also breathing heavy.

"Yea, I was so anxious I thought my head would explode, it has been so long since I've seen you," I told her.

"I know, too long, but lets not rush, I think we both need to relax a bit."

"What do you mean?" I asked, a bit confused.

"I looked your hotel up on the Internet, it has a pool," Michelle informed me.

"Yea, I guess it does, you want to go for a swim?" I asked.

"Yea, I think we should. We're both really tense right now and I think it would help us both relax." She suggested.

"Um O.K., sure. But how exactly are you going to wear a bathing suit?" I asked.

"What do you mean?"

"There's no hiding that thing of yours. It's huge, you're going to have a massive bulge in your bathing suite," I told her.

"Well I guess I'll just have to get under the water fast and hope no one notices," she replied with a grin.

I quickly grabbed a bathing suite out of my bag as Michelle pulled hers out of her purse. Once we arrived at the pool I headed into the male changing room and Michelle into the female. When I had changed into my suit I emerged into the pool area to see no one in sight. I breathed a sigh of relief; I knew there was no way the Michelle could hide her tool from anyone. I walked around the pool a to check things out. The pool was on the 15th floor of the hotel so it offered some great views out the floor to ceiling windows. There was a relatively small poll and a hot tub at the end of the pool. Just as I dipped my toe into the water to feel the temperature Michelle emerged from the changing room. She was wearing a simple black two-piece bikini. Here top was barely big enough to hold her tits as they looked like they were spilling out all over the place. Her bottom was small and only covered about half of each ass cheek. She walked towards me as I watched her tits bounce.

As she got closer I could easily see what she was packing. I knew that little bikini wouldn't be able to hide anything. The bulge in her tiny little bottoms was huge. She smiled as she caught me staring at it. "I don't think its too bad," she said with a grin.

"Are you kidding me? I could see that bulge from the other side of the pool. And I'm seeing it from the front right now!" I told her.

"Does this help?" She said sarcastically as she turned to the side. Once she turned it became even clearer that Michelle had something extra. The crotch of her bikini was jutting out in a large, round arc. "It took me forever to find a bathing suite that fit right. Most all off them just let my junk spill out the sides."

I could feel my cock quickly growing as I admired what was hidden beneath that tiny little piece of fabric. But before I had a chance to admire any longer Michelle was headed for the deep end. "Well are we just going to stand here all day or are we gonna get in?" She said.

I was still frozen though, watching her as she dipped a toe in to feel the water. "The water in the pool is heated, it feels amazing," she told me. Without another word she hopped straight into the pool. The splash made an echo in the room as she came up to the surface for air. She looked at me for a second and then motioned for me to join her. I didn't need to me told twice as I headed for the edge of the pool and dove in. The water was quite warm and it felt great. It was just what I needed to calm myself down. I had been so tense just seconds before but I already felt myself beginning to unwind. I took a breath and dove under water again and started swimming towards Michelle. I tried my best to just relax and enjoy what little time I had with here. There wasn't any time to waste being anxious or awkward.

We went on to shoot the shit for about 20 minutes or so. She asked how Brittney was and how I was enjoying school. I told her about my internship and she pretended to be interested which was nice. She explained how life in New York was tough, and very expensive. As the minutes passed I felt each of us relax more and more.

"How about the hot tub?" She asked after we were caught up. She swam over to the ladder and slowly starting climbing out of the water. I caught an amazing glimpse of her ass as she pulled herself up and out of the pool. Half of here ass was spilling out the sides of her bottom and I wanted to reach out and grab it so bad that I could barely contain myself. She looked back and caught me staring at her ass. I tried to look away quickly and play innocent but she just laughed and headed for the hot tub.

I quickly followed her up the ladder and out of the pool. I watched as she dipped her foot into the water. "Wow that's hot as hell," she cried out.

"You're such a little baby," I said making fun of her.

"Come over here and feel it, it's insane," Michelle said. Thinking that she really was just being a big baby I headed for the hot tub and stuck my foot in. I was right, she was just a little wimp.

"You are such a little girl," I said as I quickly hopped in the hot tub and sat down.

"Shut up," she said playfully. "I think I'm just gonna dip my feet in." She then sat down on the edge of the tub and slowly lowered her legs in.

"So you're just gonna sit on the edge with your calves in?" I asked.

"Yea, you got a problem with that?" she asked. I knew that I certainly didn't. I was sitting in the hot tub looking up at her beautiful body sitting on the edge of the tub. My eyes plundered up and down her entire body. My eyes finally stopped on her enormous package. The massive bulge in her black bikini was impossible to miss. While I was admiring it I saw her hand slide down towards her crotch. Just as her hand reached her bulge she started massaging her cock through her bikini. "I see you staring, is this what you want?" She asked with a smile on her face.

I didn't say a word but simply nodded. She motioned me over to her with her finger and I immediately obliged her. Just as I reached her she pulled me head up to hers and started kissing me. Her tongue vigorously explored my mouth as I struggled to keep up with her. Putting both of her hands on the back of my head she pulled me as close and possible. Kissing Brittney had become stale after so many years but with Michelle it was like I'd never kissed anyone before in my life. After a few minutes of making out I felt Michelle grab my hand and guide it down to her crotch. She used my hand to massage her massive tool and I immediately knew what she wanted. Breaking from our kiss I looked around quickly to make sure that no one had joined us in the pool area and then slowly made my way down towards her eager cock. She was still sitting on the edge of the hot tub and I was inside it, so I simply pushed her legs apart to give me perfect access to all her meat. Once her bulge was exposed to me I started slowly kissing her cock through her bikini. I heard her soft moans and I teased her to her limit. Her growing cock caused her bikini to swell even more as her bulge seemed like it would rip her bottoms in half.

It didn't take long before she could on longer handle my teasing. With one hand she reached down and pulled her bikini to the side, finally freeing her massive tool. Even semi-hard her cock was still 5 inches long, easy. She then used one hand to grab the base of her cock and the other to was grabbing at the back of my head. I opened my mouth as wide as I could as she pulled my face closer to her cock. My mouth finally met her cock and I quickly took as much in as I could. Even with her cock semi-flaccid I couldn't take her all in. Just before my mouth reached the base of her cock I felt my gag reflex fire up. I backed off her cock and brought my mouth all the way back to the tip of her head, and then dove down with my mouth again. Using my right hand I grabbed the base of Michelle's cock from her grasp and did all the work myself. I could hear her moans begin to grow with each bob I made up and down her shaft. As her moans continued to grow I could feel her dick growing in my mouth. Each time my mouth went down on her cock I was able to take less and less of her growing tool in my mouth.

"Oh yea baby that's it," I heard Michelle moan out. After a minute or so Michelle's cock finally stopped growing and I pulled it from my mouth to admire it. It looked even bigger than I remembered.

"What's wrong? Why'd you stop? That felt incredible." Michelle asked.

"Nothing's wrong," I said as I stared at her massive tool, "I'm just admiring what you've got. It looks even bigger than I the last time I saw it."

She giggled, "Yea, well, you're right, it has grown a little in the past few months I think."

"Are you fucking serious?" I said in amazement. "As if YOU needed an even bigger dick."

"I measured last night when I got hard thinking about you. 8.5 inches now," she told me with a big grin.

As Michelle sat on the edge of the hot tub I looked up at her in wonder. Who would think that this tiny, beautiful women was packing one of the biggest dicks I'd ever seen. It was a cock that would put 99% of men to shame, including myself. As I admired her tool I began slowly stroking up and down her shaft with my hand. The water from the hot tub acted like a lubricant as I let my hand glide from her base to her head. It didn't take long for her moans to start again as I quickened the pace of my hand. After a few strokes I simultaneously tightened my grip and began increasing my pace. Her moans grow louder and louder with every stroke as I continued to work her cock with my hand.

I jerked her off for a minute or two longer until she finally stopped me. Without saying a word she grabbed my hand and took it off her throbbing cock. I was confused for a second until she used my arm to pull me up to her level. I thought she was going to start kissing me but she had something else in store for me. She got up off the side of the hot tub and stood next to me, both of us knee deep in the water. Before I could do anything else she turned me away from her and bend me over the side of the tub. She undid my bathing suite and pulled it down. With my ass exposed to her she quickly bent down spread my cheeks apart with both hands. There was no hesitation as I felt her hot tongue against my asshole. A shiver was sent up my body as she started flicking her tongue all over my hole. But as soon as she started she replaced her tongue with a finger. The spit from her tongue helped her index finger slide into my hole without much resistance. I felt my hands tighten their grip on the edge of the hot tub as she added a second finer to my ass. But again, just as I had come accustomed to her fingers she took them out. I knew what she wanted and she wanted it right now. She wasn't going to wait any longer.

I looked back at her and saw her grab her cock with one and as she placed the other in her mouth. She gathered some spit from her mouth and coated her cock with as much of it as she could. Without saying a word I felt her push her cock up against my quivering asshole. When her cock pressed against my hole I could feel its girth. It felt like she was about to shove a mag flashlight into my ass. I felt her place one hand on my back as she used the other to guide her dick into me. I felt the pressure against my hole rise as she pushed forwards with her hips. The pressure grew and grew but nothing happened.

"Damn you're tight, " she said as she continued to push up against my resistant sphincter.

"It's not that I'm extremely tight, it's just that your dick is so huge," I tried to explain to her.

She grabbed some more spit from her mouth and applied it to the head of her cock and began pushing against my hole again. I felt the pressure against my hole growing again and it finally became more than my sphincter could bear. Her dick shot about 4 inches into my ass with a pop. It felt like a fire had just been set in my ass. My entire body tensed and I instinctively reached back and grabbed Michelle by the waist, preventing her from pushing any more of her dick into my strained ass. My breathing became nothing but long, deep breaths as I tried to relax my body.

It took about a minute before the pain finally started to subside. I could tell Michelle was eager because the second I took my hand off her waist she started furiously pumping away at my ass. The spit wasn't working all that great as a lubricant as she had trouble pushing more than 4 to 5 inches of her cock inside of me. It didn't seem to matter though as her moaning grew exponentially. The water splashed in and out of the hot tub as her pace quickened. After only about a minute I could feel her cock throbbing inside my ass. Her hands on my ass clinched as I could tell she was getting closer to cumming.

"Oh fuck John, I can't hold it any..." before she could even finish her sentence I felt a hot spurt of cum shoot into my ass. Michelle was virtually screaming at this point as she continued to dump her load into my colon. It must have been an enormous load as I could feel the cum oozing out of my hole and running down my leg. All the cum did help to act as a lubricant as her cock was now smoothly fucking in and out of my hole. She continued to moan as she pulled her cock from my ass and started jerking herself off. To my amazement she still hadn't stopped cumming as I felt a few more spurts shoot against my asshole.

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