The days couldn’t go by fast enough as I patiently waited for the last weekend of October. While crossdressing on Halloween seemed all too cliché, Missy and I had collaborated on quite an outfit that undoubtedly would be my most outlandish and revealing look yet. Missy and her friend Laura had decided that a trio of slutty pirates would be the perfect opportunity for Jenni to make her college campus debut. Missy said she was up for the challenge to make me undeniably passable as long as I was up to potentially taking Jenni to the next level. While I wasn’t exactly sure what that meant, I was in. How could I say no?

With a relatively elaborate plan in place to get my parents blessing for a two-day trip out of town to visit Missy, I was in the car making the two-hour trip. Missy’s off-campus, two-bedroom apartment was the perfect spot to have the freedom and space to spend the weekend as Jenni and not having to worry about concealing myself to anyone for an entire weekend. A little over an hour into the drive, I pulled into a rest area to make a few necessary adjustments. I went into a bathroom stall to put on a new lacey white bra and matching bikini panties that I would wear under my sweats. Once back in the car, I took out my makeup bag and did a light once over. I couldn’t help but notice the looks I was getting as truck drivers and other motorists walked from their vehicles to the rest stop. I fantasized about having sex with one of the drivers in the cab of his truck as I watched them, checking me out.

I was back on the road in short time and for the remainder of the trip I began to focus on Jenni and everything that went along with her. I would occasionally glance in the rearview mirror just to admire the mascara covering my lashes and the rouge on my cheeks. By the time I arrived at Missy’s place, Jenni was ready for a fantastic weekend of fun.

Missy greeted me at the door with a big hug pressing her boobs against me in a friendly, yet sexual manner that I was much more aware of after our time together.

“Oh my god! Let me see,” she said as her hands squeezed my breasts over the padded bra.

I pulled up my tee shirt to show her my new purchase.

“White! I love it! Virgin white for Jenni the virgin.”

Missy’s friend Laura came from around the corner and greeted me with a big hug as well. Like three college girls would, we giggled our way into Missy’s bedroom to check out the costumes for the party. As if the costumes themselves weren’t enough, Missy had gone all out with knee-high boots and a wild brunette wig that would definitely give Jenni an awesome look, one like never before. Missy insisted that I try on the costume which fit nicely and while the boots were a little snug, they looked and felt so sexy, I wasn’t complaining.

We spent most of the night drinking and just hanging out. When it came time to sleep, Missy insisted I sleep with her. I had brought a pair of sleeping shorts but Missy suggested my bra and panties. I was game. In bed, it was hard to resist Missy, especially as she ran her nails over my body. It wasn’t long before I was completely hard and hoping Missy might want to help me out. Instead, she had other ideas.

“I am assuming you have never been fucked before,” Missy asked.

“As in having anal sex? No.”

“Are you willing to try something?” Missy asked. “For me?”

Of course I was willing. There wasn’t much I wouldn’t do for this girl. Missy reached over to the small night table next to her bed, opened the drawer, and produced the dildo I was familiar with from our day on the back patio at her house.

“So, I think we should experiment with our little friend tonight. You never know what may happen tomorrow and you should at least know what it feels like to have a dick in that virgin ass of yours.”

As quickly as Missy had turned me on with her sensual touch, I noticed that my penis was not as excited about the prospect of experimenting with anal sex. Then again, maybe that was a good thing. I told Missy I was up for it and slid my panties off as she requested. As she applied a little KY to the dildo I rolled onto my back and got comfortable. Missy took another dab and applied it directly to my bud and slowly inserted her finger.

“Just relax. Don’t be so tense. Just enjoy the feeling,” she said as she pushed her middle finger deeper inside me.

I closed my eye and took a deep breath. Moments later I felt a second finger being inserted and pushed inside me.

“Ok. I’ll go slow but let’s see how much of this bad boy you can take,” she said as she removed her fingers and moved the head of the life-like rubber penis toward my ass. I felt the head move slowing inside and then inch by inch, it filled me up. It hurt like hell. She slowly worked it inside me, pausing at times to let me react and relax. It wasn’t very long before a good six inches was in me and Missy started to play. She slowly pulled it out to the head before pushing it back in and then starting repeating the action at a slow pace. Each time I felt it slide in and out, it felt better than the last and soon, I was becoming aroused again.

“Oh fuck this is so hot,” she said.

I simply moaned in delight. It felt incredible. Once again, my cock was rock hard and after about five more minutes of being fucked by Missy’s dildo, I felt uncontrollable waves of cum shooting all over my stomach. I watched Missy, her eyes closed, fucking me with one hand and playing with my cum with the other. As she started to lick her cum-drenched fingers her pace with the dildo quickened, becoming more forceful with each motion in and out. Her second hand slid in her shorts as she fingered herself to an orgasm in tandem to her strokes of the dildo in my ass. She released her grip on the penis allowing it to fall on the bed as she collapsed on my body, wildly in orgasmic pleasure. She rolled over and said good night.

In typical Missy fashion, night one was over.

Day two arrived with a great deal of anticipation. Missy was masterful about hiding anything that had happened the night before and her focus was all about preparation for the party. After a light day of activity, including a nice workout at the gym, it was time to get ready. Each of us had unique look but our theme was consistent across the board. My costume was a predominantly red and black mini skirt with a very frilly off-the-shoulder top. The wig was something new for me as suddenly I had a lot more hair to work with a definitely gave me a more refined look. We decided on a bandana instead of the pirate hat that would help keep my newfound locks in place. Missy did a fantastic job with my makeup as well. I slid into my boots that fit more comfortably with the black sheer stockings I had and stood in front of the mirror to admire my look.

“You look fucking hot,” Missy said looking at my reflection off of her mirror. “In fact, I think I hate you for looking as good as you do. If I were you, I’d go walk on those heels so you don’t fall flat on your face. And maybe practice bending over while you’re at it.”

“So our little practice session last night and now your comment about bending over, this sounds more like something I should expect and not ‘you never know’. What gives?” I asked.

“OK. So I’m kind of seeing this guy from the house we’re going to for the party. And maybe it kind of came up that his friend is very bi-sexual. He’s not totally sure he’s into the crossdressing thing but if he likes girls AND guys, we figured he’d love you. You’re the best of both worlds.”

As I admired myself in the mirror, I thought to myself, I sure am. I immediately said to myself that if the opportunity presented itself, I was completely going to go for it. Laura popped into the room to ask for help cinching up her costume.

“What the fuck Missy. You said Jenni was hot but Jesus! You didn’t say she was this fucking hot. God damn girl.”

Missy got up to help Laura and slapped me on the ass as she did. “Go pour us a shot of something, bitch.”

The girls finished getting ready as I poured and delivered a few shots, adjusting nicely to walking in the three-inch heeled boots. After another hour it was time to go. Missy touched up my lips and makeup a little and we were off. We were picked up by a pledge from the house we were going to who was clearly uneasy with the overly suggestive nature of our conversation and line of questioning including if he had ever sucked another guy's dick, how big he was, and my favorite, if he would ever dress as a girl if he was asked.

Even a year ago, I would have had a nervous stomach and would have been terrified at the prospect of going into a party on a college campus dressed as a girl. Now, I felt I was just one of the girls, going to a frat party, looking for a hot dude with a nice dick. We each gave our driver a kiss on the cheek as we got out of the car and whether it was the four shots or just my newfound confidence, I decided a little squeeze between the legs would be a nice touch. We all laughed.

Once in the party, Missy connected with her friend Aaron, whispered in his ear as she looked my way, and brought him over to meet me.

“Jenni, it’s incredible to meet you. Missy has told me so much about you and you look amazing. Have fun tonight. I told Missy my friend Eric will be here in about an hour or so. He’s an amazing guy and he’ll really be into you.”

I thanked him for everything and the invite. Laura and Missy returned with a beer and we were ready to mingle. The party was a blast. The three of us looked amazing and I blended right in with our trio and the party. The amount of guys that came up to us was almost overwhelming but between my confidence and newfound desire to find a cock to play with, I loved it. We were there for a little over an hour when Aaron walked up to introduce his friend Eric. Eric was twenty-one, in tremendous shape, and at six-foot-three, was taller than me even with my heels. By this time, Laura had wandered off with a guy and Aaron clearly was looking for a little alone time with Missy. I very quickly found myself alone with my newfound friend amidst a sea of college-age partygoers.

Eric and I carried on some semblance of a conversation over the noise for a while before he suggested we go to a more private space to talk. He took me by the hand and led me through the sea of people, grabbed two beers, and led me down a flight of stairs into an area that was clearly reserved for the upper classmen who needed a more intimate space. We found an empty love seat and got comfortable. We made small talk for a while before getting to what was on both of our minds.

“So, Aaron has told me a lot about you and Missy has shared quite a bit as well,” Eric said. “Missy in particular seems to think we’d make a cute couple. What do you think?”

I put my hand on his shoulder and realized very quickly just how jacked this guy was. I decided to rub down his arm to check out his tricep. His muscle was rock solid.

“I think we might get along just fine,” I said with a smile.

He placed his hand just above my knee, moving it up my leg as he softly rubbed my leg. He leaned in for a kiss and I willingly obliged, putting my hand back behind his neck to pull him closer. We made out on the couch oblivious to everyone else around us. His delicious lips pressed against mine and when his tongue went looking for mine, I was happy to offer it back. Eric was a mature older man, all man, and yet we both knew he had a little secret. As did I. Looking to test our boundaries, I allowed my other hand to find his leg and slowly slid it between his legs. His cock was rock hard.

“We have two options,” he told me. “First, we just make out here but that’s as far as it can go. Those are the house rules.”

“Or two?” I asked.

“The second option is that we let Aaron and Missy know we’ve gone back to my place and they can meet us there later.”

“I think I like option two the best.”

It was roughly fifteen minutes later that we were walking into Eric’s apartment. Aaron and Missy would be joining us later but for now, it was me and Eric. I used the bathroom to check my makeup and make sure I was still looking good. When I walked out, Eric was waiting for me on the couch. I sat and after a few minutes of playful banter, we started to kiss. It started lips on lips, quickly progressed to a delightful French kiss, and quickly proceeded to Eric on top of me. Our hands began to explore each other’s bodies. I couldn’t help but be completely aroused and despite Missy’s constant reminders to control myself, there was no controlling my raging hard-on.

It was a few minutes in when Eric’s hand made his way between my legs and rubbed my cock while his other hand rested behind my neck as we continued to kiss. My hands were both on his muscular and very toned ass. I could feel his rock-hard dick rubbing against me as well. After several minutes, we mutually decided that the couch was not only too small but that Missy and Aaron might be returning soon as well. We made our way to his bedroom. My boots came off, followed by my costume, leaving me standing in my bra and panties for Eric to look over. The silence continued as Eric slid his pants off. I helped him removed his shirt and rubbed my hands on his chest.

As we fell onto the bed, my cock fell out of my panties. As I moved to try and conceal it again behind my silk panties, Eric asked why bother, and started sliding them off. We both positioned ourselves side by side and as Eric crossed his leg over mine, our cocks touched for the first time. It was the first time this had ever happened and I wasn’t at all surprised to feel my cock getting harder. We kissed for a few minutes before I started licking his neck and then his chest. My hand found his raging hard first and soon my tongue finished its journey downward.

Taking Eric’s cock in my mouth was euphoric. While best described as a modest seven-inch penis, it was so hard that it felt twice that size. The taste of his cock was incredible. I don’t know what it was but having his cock in my mouth was like no other. My lips and tongue worked his hard-on, taking an occasional minute to suck each of his balls. As I was licking his shaft back to his head, his cock quivering as I did, Eric popped the question I had been anticipating all night.

“Do you want me inside you?” he whispered in my ear.

“Oh my god yes! I thought you would have never asked.”

Even after fumbling with a condom and taking more than a minute to find a little lubricant, both of us were still fully aroused. I remember feeling the head of his cock pressing against the bud of my asshole. At first, my reaction was to resist and I could feel myself tense up. I took a deep breath to relax and felt the head push through and rather quickly the rest of his cock fill me up. The combination of both pleasure and pain was enough that I let out a relatively loud almost agonizing groan but at the same time I reached behind to push him back inside me as he started to withdraw.

“Nice and slow baby. It feels amazing. Just go nice and slow.”

Eric delivered just that. His slow pace of withdrawing and reinserting his cock inside me was perfect. He would occasionally hold his head right outside my hole before pushing back in and doing the same buried deep inside me. It was incredible.

I’m not sure what overcame me but after about five minutes of sensual intercourse, I decided a little dirty talk was in order and blurted out, “So do you fuck all your sluts like this? Stop playing around and fuck me.”

“Oh now you want it harder, huh?” as he thrust his hips hard into my ass, burying his cock deep into me.

He turned me over, grabbed me around my waist and started to thrust hard into me at a much more rapid pace.

I never would have imagined the pleasure I was getting by this man fucking me with the ferocity that he was. I could hear skin on skin as his hard cock pummeled my virgin hole. Each thrust seemed to penetrate me deeper and deeper. My cock was pressed firmly against my stomach. I could feel it get harder as I was being fucked and knew I would cum very soon. I continued my profane banter, now yelling at Eric to fuck me harder as he responded calling me a dirty whore and his little high school slut. It wasn’t long after that he made a final hard thrust and then buried deep inside me. I knew he must be coming. He rolled off to the side slowly sliding the cum filled condom off as I repositioned to suck his cock.

It didn’t take long for his dick to get real hard again and I decided I wasn’t waiting for him to fumble around with shit. I turned around and sat down rather abruptly letting him enter me, this time naturally filling me up without the condom. This time I was stroking my own cock while he fucked me. There were few words said as I felt him getting rock hard inside me. I moved my ass up and down on his cock at a much more rapid pace than before. Every time I lowered on to him his cock felt deeper and deeper inside of me. The sound of our flesh slapping against each other was a complete turn-on. I could feel my own cock growing as my hand kept pace with our sex.

It was moments later that I shot my first load of cum into my hand followed by wave after wave. I took my cum soaked hand and started to wipe it on my chest when Eric told me to lick it off my hand. I obeyed. I inserted three fingers into my mouth and began to lap up my own cum, licking as much as I could, turning back to show my lover that I was indeed the cum slut he thought I was. His cock grew hard inside and it wasn’t long after that I felt my once virgin love hole being filled with his cum. It was a feeling that I would never forget. After grinding on his dick for another minute, I rolled off my lover and onto the bed. I could feel his load inside me and it made me feel like I never had before. We laid there in silence for a few moments to catch our breath.

“I’m sorry for being so aggressive but I really wanted you inside me again,” I said to break the quiet.

“Are you kidding me? That was absolutely the most incredible sex I’ve ever had. I would fuck you a million times tonight.”

“A million times would be A LOT of sex.”

“And I’d love every time. I want you to stay the night if you would. I’ll give you a tee-shirt and shorts to wear. I just want to fuck you as many times as possible before you have to leave.”

“Well if you do, maybe you should wear a condom next time. I mean the last thing either of us need is you getting me pregnant. I mean that last time may have done the job for sure.” We both busted out laughing.

“Oh my god, you would be the hottest pregnant chic I know. Do you think about things like that?”

“Until two years ago or so, I had never even worn a piece of girl’s clothes. I never thought about being with a guy. This is all very new. Very new, but also, very hot.”

Eric rubbed my belly.

“Could you imagine what that would be like?”

“Absolutely not!” I said rather convincingly but at the same time completely lying. I was incredibly turned on by the thought and my mind wandered to what it would be like. I put my hand on his cock.

“This is amazing. Go get us another drink and let’s do it again.”

I didn’t need to say it twice. Eric was out of bed and on his way to get us a drink. I went to the bathroom to refresh my makeup. I was a mess. I did my best to touch things up and came back to find him back in bed stroking his cock.

“Don’t you dare. That’s my job,” I said climbing back into bed. I took his cock in my mouth and went to work.

We woke up around 10 AM the next morning to Missy pounding on the bedroom door. She reminded me I had to be getting home and we had a little work to do before I could go. Leaving Eric was incredibly hard that morning. Aaron gave us a ride back to Missy’s place. I just kind of stared out the window until we got there. I wished I could have stayed. I wanted Eric inside me again, fucking my brains out. My mind was anywhere but there. We got into her apartment and Missy snapped me out of it.

“He’s one guy. Go back home. Have fun. But I have to know, is he big?”

We both laughed.

“Fuck yeah, he was big. And it was amazing.”

Missy and I talked while she helped me get makeup-free and ready to return home to life as Jeremy. I was set and ready to go within the hour. After a kiss from Missy, I was off. I drove home wrestling with my emotions, conflicted with my sexuality, and thrilled to have had an unbelievable experience like I did. I couldn’t help but think the entire way, what was next?