tagTranssexuals & CrossdressersHigh School Friend Has A Secret Ch. 04

High School Friend Has A Secret Ch. 04


My story last left off with me cheating on Brittney for a second time. While she was gone I had fucked and been fucked by one of her best friends, named Katie. Brittney had been o.k. with me sleeping with Michelle but I wasn't sure how'd she'd feel a second time around. Right when she got home I decided I wasn't going to keep it from her, I'd tell her everything.

To my surprise Brittney already knew all about it. Once Kaite found out about me and Michelle she asked Brittney if she could have sex with me too. Katie was in the same position as Michelle; it being nearly impossible for her to have safe sex with someone she trusted. Brittney told me she was a little apprehensive at first but eventually gave in.

"I knew both of you were going to have sex when I left," Brittney said.

"Well if you and her both knew, why the hell didn't she tell me? She didn't say anything about you knowing." I said.

She laughed, "Yea, Katie said she wanted to mess with you a bit. She thought you might enjoy it more if you thought you were doing something wrong. I didn't mind her not telling you that I knew, I think it's hilarious you had to suffer over telling me about it for a few days."

"So you're not mad about me and Katie having sex? Not at all?" I asked confused.

"We've gone over this before you dork. I know that you aren't going to dump me for a transsexual, I know that its purely sexual, so I'd rather you fulfill your fantasies as opposed to keeping it bottled up all your life." She said as she stared into my eyes. "But if I ever catch you having sex with a girl, I'll kill you!" She smirked.

"Believe me, you're all the woman I can handle, I have no desire to have sex with any other women," I replied. "So am I allowed to have sex with Katie again?"

"Yea sure, just invite me next time," she said as a smile crept across her face.

So I was in the clear. After worrying for days about telling Brittney it turned out that she knew about me and Katie all along. And not only was I allowed to have sex with Katie again, Brittney wanted to join. Just thinking about a threesome with me Katie and Brittney sent my over the wall. The thought of watching Katie pound Brittney's little pussy while she sucked on my cock made me crave our threesome more and more.

By the time Brittney got back from babysitting there were only a few more days of spring break left. I wanted so badly to have our threesome but had no idea how to bring the topic up. Time was running out and I had to do something about it before I went back to school. I knew I'd go insane thinking about it all semester if it never happened. I didn't want to just casually bring it up in conversation but I was hoping a few drinks might lighten the mood and lead us into the bedroom.

My wish finally came during the last night of spring break. One of my best friends called me on Saturday afternoon and told me he was having a end of spring break party for everyone that was still in town. I immediately told him I'd be there and quickly informed the girls.

"Ryan's having an end of spring break party tonight, do you two want to go?" I asked Brittney and Katie.

"Yea sure, we don't have anything else planned for tonight," Brittney said.

"That sounds fine to me, do you know what time it starts?" Katie asked.

"I dunno, we'll probably show up around 10, 10:30 if that's fine with you two." I replied.

10:30 it was then. The night was set and it was all I could think about. I played the night through my head over and over. I spent the entire rest of the day fantasizing about how our night could turn out. All the positions we could try, who would fuck who. There were endless possibilities with the three of us. But I knew that none of it would happen if I didn't initial something. Just a little spark would be enough to get the three of us going.

10 finally came and I could barely contain myself. My cock had been pretty much rock hard all night just thinking about what could happen. "It's about 1015, you two want to start heading over there?" I asked from the living room.

"Yea, I'll be out there in a sec," I heard Katie say from her room.

Brittney walked in just a few seconds after I called her and she looked amazing. She was wearing a short jean-skirt and a black top that really showed off her tits. Her tits weren't huge, about a B cup, but when she wore a push-up bra with this top they somehow looked huge. Katie walked in just after Brittney and she looked equally amazing. She was wearing a simple outfit, just jeans and a shirt, but she looked hot as hell. Her top was extremely tight around her large tits and just barely came down to her waist, exposing her stomach just a little. My stomach felt like it had dropped out my ass when I looked at the two of them standing there. I tried to compose myself, "Ready?" I asked.

The party was your usual house party. Good keg beer, drinking games, and lots of old friends. For the first time all day I relaxed and had a good time. I needed something to take my mind off the night ahead, it was starting to kill me just thinking about it. The night was going well. I after about an hour and a half of drinking I was starting to feel it. All the drinking games were beginning to take their toll on me; Katie and Brittney were right there with me too. A nasty game of circle of death put the three of us exactly where I wanted us to be.

I could tell Brittney was starting to get buzzed because she started getting very affectionate. Whenever she gets buzzed she starts kissing my neck and grabbing my leg and tonight was no different. Katie's tell-tale sign was her uncontrollable laughter. Whenever she started feeling it she couldn't stop laughing to save her life. With the two of them beginning to relax and enjoy themselves I knew I had to make my move if I wanted this threesome to happen.

"I've got to take a piss, save my spot," I yelled to everyone at the table. I walked over to the bathroom but the line was fairly long. Knowing there was a 2nd bathroom upstairs that no one ever used I headed upstairs. In the bathroom I began collecting my thought, trying to think about how to initiate a threesome. Did I just flat out ask the two of them? Did I start having sex with Brittney and then ask her if she wanted Katie to join us? I'd certainly never done anything like this and had no idea how to go about it. As I started washing my hands, still mulling things over in my head I heard a knock at the door.

"Open up," said a girly voice from the other said of the door.

"One second," I replied, figuring it was some drunk bitch that didn't want to wait downstairs.

But when I opened the door I saw Katie standing there. "Oh, hey, didn't know it was you; go right ahead, I'm done," I said.

Without saying a word he put her hand on my chest and pushed me back into the bathroom. She shut the door behind her and instantly planted her lips on mine. The release I needed had finally come. I had been longing for it all night and it came when I least suspected it. We started passionately making out as our hands explored each other's bodies. I pushed her up against the wall as we gasped for breaths between kisses. I immediately made my way to her ass and began groping each cheek in either hand. She let out a soft moan as my hands squeezed her ass as hard as they could. She followed suit as I felt her hands start to work their way down to my ass. The groping and grinding intensified with each passing moment.

"Call Brittney," Katie murmured between breaths.

"You want me to invite her up?" I asked?

"Yea, I know she would want to be here for this," Katie replied.

Katie began passionately kissing my neck as I pulled out my cellphone and texted Brittney; Upstairs bathroom, NOW. Within 30 seconds I heard the knock on the door. Katie and I broke from our embrace and Katie opened the door and peeked though the slit in the door. I watched as Katie reached outside the doorway and pulled Brittney into the bathroom with the two of us. Just as she saw the two of us standing together in the bathroom a big smile crept across her face. Once Katie noticed her excitement she grabbed Brittney by the back of the neck and pulled her mouth towards hers. The two of them met with so much passion that I thought I might bust my nut right there. I watched in awe as these two beautiful girls made out in front of me.

I watched for what seemed like an eternity. With each passing moment the room became hotter and hotter. Their hands began exploring all over each other's bodies just as me and Katie's had minutes before. I watched as Brittney's hands crept underneath Katie's shirt and up to her large breasts. Katie's head tilted back with a moan as Brittney began squeezing Katie's tits underneath her shirt. Brittney had surprisingly taken the dominant role and was all over Katie. After Brittney had shown Katie's tits the proper attention her hands fell down to her waist.

Brittney teased her as she let her fingers slowly slide beneath the top of Katie's jeans. Luckily there wasn't too much teasing as Brittney began to unbutton Katie's jeans. The denim gripped her perfect thighs tightly as Brittney slowly pulled Katie's jeans down to her knees; exposing her red cotton thong. I could instantly make out the outline of Katie's bulging member beneath the tiny piece of fabric. But before I had a chance to enjoy the view any longer Brittney turned to me and pulled me face to hers, kissing me with so hard I thought my jaw would break.

But the kiss was short-lived; Brittney pushed down on the top of my head and motioned me down to Katie's eager groin. Without saying a word I dropped to my knees and positioned my face right in front of Katie's massive bulge. As Katie and Brittney continued to kiss and grope each other I began slowly kissing around Katie's groin. I started with each thigh, starting at the outside and making my way closer and closer to her cock. Kissing up and down her inner thighs I could hear her beginning to moan louder as Brittney struggled to keep her quiet.

My teasing continued as Brittney reached down with one hand and started caressing Katie's bulge. Between my teasing and Brittney's groping I wasn't sure how much longer Katie would last. I watched out of the corners of my eyes as Brittney delicately stroked Katie's bulging member, by now her cock was almost rock hard beneath her panties and it was begging to be let free. Brittney finally obliged as she pulled Katie's red thong aside, allowing her cock to pop free.

Just as Katie's cock was finally set free Brittney put one hand on the back of my head and used the other to aim Katie's 7 inch cock right towards my mouth. I couldn't believe that Brittney was being so open and aggressive with this threesome. She was the one guiding Katie's cock into my mouth. Not wanting to disappoint Brittney, I opened my mouth and allowed Katie's member to slid deep into my mouth. I immediately went to work on Katie as I began sucking back and forth on her throbbing dick. As I continued sucking I looked up to see that Brittney had pulled Katie's shirt up above her breasts, exposing them for her to suck. As I worked Katie's cock Brittney was grabbing and sucking on Katie's big tits.

"Oh my God," Katie started moaning. She was getting louder and louder and I hoped that she hadn't forgot that we were in the bathroom at a party. I certainly didn't want to draw any attention to us. Luckily Brittney noticed this and tried to cover Katie's mouth with her own. Brittney and Katie began kissing again as Brittney tried as hard as she could to keep Katie quiet while I sucked her off. Her nice long cock was easy to work on. I kept varying my pace, sucking slowly, then fast, then slowly again. I was using one hand to cup her round balls and another to hold the base of her cock. With her cock held in position I let her cock slowly pop out of my mouth before I dove back onto it. I still wasn't about to take her whole length inside my mouth, in fact I could barely even take half of it. Katie didn't seem to mind however has her breathing grew faster and faster. Knowing how much I loved it when Brittney sucked on my balls I knew I couldn't ignore Katie's. I took her cock from my mouth and dove toward her quivering sack. With one hand I furiously jacked off Katie's dick as I sucked on her perfect nuts. I tried my best to be carful as I stuffed almost her entire sack into my mouth. With both her balls in my mouth I used my tongue to please her nuts. After her balls had been given adequate attention I stuffed her cock back into my mouth.

"Ooooooooooohhhhhh, I'm going to cum," Katie whimpered through clenched teeth. Having heard this Brittney began fondleing Katie's tits again as I quickened my pace on Katie's. Her big cock began to swell even larger as I could feel her getting closer and closer to cumming. As she neared her climax I grabbed the base of her dick with my hand and started to jack her off while I continued sucking back and forth on the front of her cock. Katie's moans continued to get louder until she finally released in my mouth. I tired my best not to gag as stream after stream of hot cum shot down my throat. At this point Brittney simply resulted to covering Katie's mouth with one hand to try to block out some of the noise; she was practically uncontrollable. I continued to suck up and down Katie's shaft as the last of her hot cum flooded my mouth. I tried to swallow as much as I could but cum shot out between her cock and my mouth and Katie's cock was still covered with cum as I sucked up and down her shaft. I continued to slowly jack off the base of her dick in order to get the last little bit of cum out. When she finally finished I backed up a bit to admire her beautiful cock. It was still semi-hard, about 6 inches long, and covered from the middle of her shaft to the head with cum. Unable to resist I dove back towards her dick to take it in my mouth one last time.

"Lets get back to my place, NOW!" Brittney said with a smirk on her face. All of us knew their was no reason to try keeping this quiet any longer, it was time to let loose. Still trying to catch her breath Katie pulled her shirt down over her breasts and stuffed her still cum coated cock into her little red thong. Just as she pulled her jeans up Brittney opened the door and pulled the two of us out before we could say a word. We didn't bother saying goodbye to anyone. Katie was flushed red and could barely walk straight so we headed straight out to the car.

I ran around to the driver's seat and the two of them both hopped up front together. Brittney sat in Katie's lap and the two began kissing again before I had even turned the car on. I had no idea how I was going to keep my eyes on the road but I knew I wanted to get home as fast as possible. Trying to stay concentrated I turned the engine over and headed down the street. Before we made it to the first light Katie and Alex had pushed the seat all the way back to give themselves more room. With Katie sitting in the seat Brittney got down on her knees in the footwell, kneeling between Katie's legs. Before Katie had a chance to catch her breath Brittney unbuttoned her jeans again and pulled them completely off. Both of them breathing heavily, Brittney's hands dove towards Katie's panties and pulled her soft cock out of her thong. With Katie's cock still covered in cum from earlier Brittney gave her no time to rest. She started licking up and down Katie's cock, getting every last drop of cum off Katie's dick.

I couldn't believe that Katie would have any energy after the bathroom but after only a few seconds her cock began to grow again. Each time Brittney bobbed up and down on Katie's cock it grew bigger and bigger. I Desperately tried to keep my eyes on the road but could always see Katie's growing cock out of the corner of my eye. As Katie's cock finally reached its full length Brittney made her move. Failing to keep my eyes on the road I watched as Brittney pulled up her skirt and straddled Katie who was still sitting in the passenger seat. Brittney had to lean forward towards Katie's face to keep from hitting the roof but as she did the two of them began kissing passionately. The two of them were now full on making out with Katie's cock grinding against Brittney's exposed panties. Brittney began thrusting back and forth along Katie's shaft as her moans grew louder and louder.

Finally Katie had enough teasing and reached down for her moist cock. With one hand she reached down and pulled Brittney's thong aside, exposing her aching pussy. With the other hand she guided her member directly into Brittney's ass for the first time. Brittney let out a long and loud moan and Katie thrust her cock deep inside her. At this point I thought for sure that we were going to crash. Katie grabbed onto Brittney's ass with both hands now and began fucking Brittney hard. Brittney leaned down towards Katie and the two of them began kissing again, the both of them moaning louder and louder.

"Holy shit your little ass is tight," Katie moaned to Brittney.

Just as I thought I was either going to nut or we were going to die we finally reached the house. I pulled up into the driveway, the two of them still feverously fucking each other. As I stopped and turned off the car neither of them even noticed, they were so caught up in the moment that they hadn't noticed we were home. I reached over and put my arm on Brittney's back as she looked over to me.

"We're home," I said with a huge grin. The two of them finally slowed, Katie's cock still buried in Brittney's ass. With both of them trying to catch their breath I opened my door and headed for the side door. Just a few seconds afterwards Brittney fan up to the door with Katie right behind her. Katie hadn't even bothered to put her pants back on as her hard cock bobbed up and down as she ran into the house. Thank goodness our driveway and side door were hidden by a large hedge or it could have been an interesting night if one of the neighbors saw us.

Before we even made it to the bedroom Brittney started simultaneously kissing me and undoing my pants. As she took my pants off she dropped to her knees and started sucking my already hard cock. Katie walked up to the two of us and started kissing me as her cock pointed straight at Brittney's face. Brittney then stopped sucking my cock and took Katie's cock and mine in each hand. Katie and I laughed as Brittney looked up at us with a grin, holding both hard cocks in her hands. She took turns sucking on each dick. She'd spend a minute or two on mine and then switch over to Katie. I think I liked watching her suck off Katie even more than I liked having my own cock sucked.

After a few minutes of being sucked off I couldn't take it any longer. I grabbed Brittney by the waist and bent her over on the couch. Just as Katie had before, I didn't even bother undressing her. Simply sliding her little thong aside I slide my cock into her very wet pussy. She was still very moist from the pounding that Katie had just given her so I quickly gained speed and was fucking her furiously within seconds. Just as I started slamming in and our of her Katie sat down on the couch in front of Brittney's face and guided her cock into her mouth. The sight of it all was almost too much for me to bare as I struggled to hold my load.

"Wow your girlfriend sucks a mean dick," Katie said as we made eye contact.

"You're telling me," I said as I watched Brittney's head bob up and down on Katie's cock.

"How does her pussy feel?" Katie asked.

"Tight as hell, you want to try it?" I replied with a smirk.

"I bet it does, now let me get a piece of it," Katie said.

I then pulled my cock from Brittney's pussy and allowed Katie to take over. Just as before Katie pulled Brittney towards her and made her straddle her cock. Katie quickly inserted her dick into Brittney and started pounding her all over again. But this time I had perfect access to Brittney's exposed ass. As Brittney rode Katie's cock I started slowly playing with her ass. I quickly ran to the bedroom to grab some lube and rushed back. Squirting a little bit out on my finger I began massaging Brittney's sphincter. After a bit of massaging I worked my index finger into her hole. She let out a soft moan as she reached back and spread her cheeks farther apart, giving me the go --ahead. I'd stuck fingers in her ass before while we fucked but never anything more than a finger. This would be her first double-penetration experience. After working a couple fingers into her hole for few minutes I generously lubed up my cock started pressing it up against her hole.

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