tagTranssexuals & CrossdressersYour Best Damn Girlfriend Ever

Your Best Damn Girlfriend Ever


There are times in a young man's life when it is so full of fun and sex that it's a wonder they survive. College is one of those times for many young men and it certainly was for me. I attended a small private collage in southwestern Ohio at a time when the world seemed to be totally focused on it's self. Yea, it was the late 80's and the me decade was in full swing. I can't say that I immersed myself in the culture of the times, but just like walking across a muddy field you can't help but get some on you.

I was in and out of several relationships with girls of many different types but couldn't seem to find that one woman who rocked my world. Well, at least not for more that a few months. The fall of my senior year there was a new girl on campus, a cute tall blonde with a bright smile, blue eyes, and a figure that drew my eyes to her whenever she was in sight. I was in between girl friends and thought that I should go and introduce myself the first chance I got.

I saw her on and off for the next couple of weeks and never could get a chance to talk to her. She was always across the green or I was running late for class. It was starting to seem like I was just not supposed to meet her. Then one day I was down on my knees getting my mail out of my mailbox in the student union when this nicely shaped pair of long legs stopped beside me. I looked over at them and then allowed my eyes to roam up along the shapely body to pretty face of the owner. It was the new girl and she was getting her mail out of one of the top mailboxes. I finished grabbing my mail, the usual credit card offers and a note from home, then turned to face my new neighbor. She was wearing a short denim mini skirt and a tee shirt with some band on it I hadn't heard of yet. Her blonde hair was teased up pretty big and her makeup looked great.

"Hi, I'm Thomas." I said as I stood up and extended a hand. I knew she was tall from seeing her across the green with other students, but I had no idea how tall she really was until I was standing beside her. I'm just a tick over 5'9" and my eyes were level with the bottom of her chin.

She flashed me a brilliant smile and said, "I know. You've been looking at me so much lately I started asking around about you." My face turned bright red at being truly busted. I sheepishly replied,

"Guilty on all counts."

"You know you have a bit of a rep for being a womanizer," She stated flatly. "But I think you just haven't found the right girl yet so I was wondering if you'd like to be my boyfriend." I was struck speechless. My mouth wouldn't seem to work at all so she filled the silence with, "I'm sure I'd be your best damn girlfriend ever!"

I looked at this beautiful girl and couldn't believe what I was hearing. Not only was she interested in having me be her boyfriend, but she was basically telling me she'd be the best one ever! Finally my brain slipped into gear and I blurted out,

"Are you kidding? I'd love to be your boyfriend!

"That's really cool!" she exclaimed. "Why don't you pick up a bottle of white wine and come by my room in Jacobs Hall. Then we can get to know one another a little better." She said with obvious meaning. "It's room 426, at the end of the hall. My roommate transferred to another school so we'll have the room to ourselves." This beautiful girl leaned down and gave me quick kiss on the lips then said, "I've got to get to my Business Admin class, so come by around 6:00 and bring some snacks with the wine." She turned to leave, stopped, then turned back and gave me another quick kiss. "By the way, my name's Angel." She said quickly, then turned and walked away.

I watched her go. Her nice round ass swaying back and forth while her long blonde hair bounced with each sexy step, she looked like a runway model on a catwalk. I couldn't believe my incredible luck. As those long legs went through the glass doors of the Student Union and out into the warm fall sunshine I tried to imagine how they'd feel wrapped around me later that night. Oh boy, but how far off the mark was my imagination.

A Long Afternoon

I floated my way down to the local alcohol purveyor in a happy daze of sexual anticipation. I stressed over the wines to the point where the sales lady finally came over to me to make suggestions. I was holding a $4.99 bottle of chardonnay in my hand when she asked me if she could help. I delicately told her that a beautiful girl had invited me to her room to "get to know one another". With a knowing smile the woman took the bottle from my hand and picked up one from the shelf above it. Without saying a word she showed me the alcohol content of each bottle. As a college student there's one thing I've definitely learned, alcohol content is everything. I splurged and bought the $9.99 bottle, some cheese and crackers, and one of those roses that stores carry wrapped in plastic. I was now loaded for bear!

On leaving the store I looked at my watch. It was 1:48. Only four hours and twelve minutes to go. Shit.

I got back to my room and unloaded enough beer out of the frig to put the wine in to start it chilling. The lady at the store told me it needed to be chilled. Not wanting the beer to sit around and get warm I popped the top on one and looked at my desk clock. 2:10. Three hours and fifty minutes to go. Damn.

I had another beer and turned on the tube. I knew I should work on my physics project, but I also knew there was no way I'd be able to concentrate on it with Angel's long legs still emblazoned on my eyes. The clock said 2:37. Three hours and twenty three minutes left to go. Fuck!

It seemed that time just refused to move at any normal rate for me. As it got closer to the anointed time, (Imagine a choir singing 'Halleluiah!!!') the damn clock seemed to be coming to a complete stand still! Just when I was starting to think I was trapped in some rip in time my stoner roommate came be bopping into the room. I'm in a pretty pissy mood by this time so I deliver the crushing line,

"If you keep blowing of your psych class there's no way in hell you'll pass it, even if you are some kind of psychology 'prodigy'." With some small distain in his voice he replied,

"Dude, I'll have you know that I haven't missed a class in three weeks. I'm like totally stoked about studying old Siggy. That Dude was one seriously messed up old man." In a conspirators voice he continued, "I think he had a thing for his mom and that just ain't right dude!" I looked back at the clock and asked,

"Did you get out early? It's only a quarter after five."

"Dude it's almost six, your battery must be going in that clock, I told you to get one of the plug in..." Stoner boy didn't get a chance to finish because I was franticly grabbing my stuff and sprinting from the room. Thankfully our campus wasn't very large and as I went blazing past the clock tower on the commons it showed that I had four minutes to make it to her room. I put on an extra burst of speed.

Getting Acquainted


I'd run track in high school, but that was a long time ago and there was no trace of that conditioning left in my body. When the elevator got to the fourth floor I was still breathing pretty damn hard. I took a right off of the elevator and jogged to the end of the hall to stand panting in front of my new girlfriend's door. I knocked at the door and heard her call,

"Just a second." I listened as she moved around in her room for a moment then the door opened and there stood Angel. She had on a pair of jeans that had so many holes in them they were more like shorts and those long legs were so sexy showing all tanned and smooth through the holes. She had on a skin tight wife-beater muscle shirt and you could easily see her lacy white bra through the shirt. She smiled a big smile and said,

"You're breathing pretty hard Thomas, you must be very excited to see me again." All I could do was nod. She was a vision of college girl sexuality. "We can't get to know one another very well here in the door way, well...I guess we could, but the RA might get a little excited about it, so why don't you come inside."

Angel stepped aside as I walked into a room where my views on life and sexuality were about to change drastically. I looked around the room and it appeared to be decorated the same as any other young college woman's. About the room were scattered the usual books and papers, pictures filled with smiling and laughing people. On the floor there was a big soft rug with pillows strewn over it and it was there that Angel plopped down indicating with a hand that I join her.

Without a word she took the bottle of wine and expertly opened it with a corkscrew she had ready. Grabbing a couple of wine glasses she filled each one about half full, re-corked the bottle, then turned to one side and slid it into her frig. I was a little nervous so I took a big swallow of wine hoping that it would quickly take the edge off my nerves. Usually I'm very comfortable around girls, but for some reason I didn't feel that way with Angel.

She sipped her wine then said,

"So tell me about yourself."

"Like what? What do you want to know?"

"Everything. What type of music you like, movies you like, foods you like, sexual positions you enjoy. Just everything."

"Well...I like rock music, action adventure movies, seafood, and pretty much any position you're willing to try."

"Good, you're open minded. I like that in a boyfriend."

"So...what about you? What do you like?"

"I like lots of different types of music, rock to reggae, jazz to blues. Action adventure movies are good but I must confess that I like chick flicks." she said with a laugh. "Seafood is yummy, but nothing beats a nice thick steak cooked medium-rare. I love sex and all positions, especially the ones where I'm dominant. I must warn you that when it comes to sex I'm a pretty take charge kind of girlfriend and when I want to have sex I don't easily take no for an answer. So if you don't like to have sex too often you might want to think again about being my boyfriend."

"If you're trying to scare me away I don't think threatening to have too much sex with me is the right way to go about it."

Angel smiled a knowing little smile and said, "Oh, I have no intention of scaring you away. I just want you to know what you're getting into and give you a fair chance to back out gracefully. I've talked with some of your ex-girlfriends and while I didn't get any specifics, they all indicated that you like sex a lot and some even alluded that you could be a little kinky." I blushed and tossed back the rest of my wine. You let a girl use a strap-on on you one time and they think you're kinky. Hell it was her idea! 'I just want to know what it's like for a guy.' Mandy pleaded. Later I found out she'd made a bet with a girl friend of hers that she could get me to do anything. The girl friend asked her if she could get me to let her bone me with a strap-on, to which Mandy said, 'No problem.' I guess Mandy was right. Angel refilled my glass as I said a bit defensively,

"Well, I guess it depends on what you'd call kinky. I would prefer to just consider myself open minded, as you pointed out earlier." Angel chuckled as she handed back my full glass and said,

"I'm not judging. I'm actually hoping you're very open minded and very willing. Those are two qualities that are an absolute must to be my boyfriend." I took another long draw on my wine glass as I digested her words. Here was a girl that professed that she loved sex to the point of not taking no for an answer and telling me if I thought I couldn't keep up I'd best move on. How could I turn down a challenge like that? I tossed back the rest of my wine, sat the glass out of the way and leaned over and kissed Angel hungrily. Not only did she respond in kind, but the next thing I knew my mouth was full of her tongue. My cock instantly stiffened in my pants.

We continued kissing as I slid my hand up and down along her ribs. She sat her glass down on the floor then grabbed my hand and placed it on her breast. It was firm and round with a hard nipple poking into the palm of my hand. I squeezed and rubbed her breast, pinching the nipple occasionally as she moaned into my mouth and tried to stick her tongue down my throat. She was on fire! Her hands were all over me, groping and rubbing me roughly, gripping me so tightly that I thought I might actually have some bruises. Then Angel really surprised me, she shoved her hand down the back of my pants and started rubbing my ass. She squeezed my ass cheeks for a few minutes then slid her hand between my cheeks and stuck her finger as far as she could into my asshole. I grunted into her mouth and tired to struggle a little, but she didn't slow down a bit and if anything became even more excited. As she eagerly fucked my ass with her finger she continued rubbing her body against me and thrusting her tongue into my mouth. Angel was very turned on and so super horny she was almost out of control. With her finger deep in my ass I thought, 'Damn, I think I'm being raped by this girl!' But I didn't struggle too much.

Finally she pulled her finger out of me and broke the kiss. She said in a husky, lust filled voice,

"Take your clothes off!" I hesitated for a second, unsure of what I was getting into, but as I watched her pull her shirt over her head revealing her round bra clad boobs it got me started on my own shirt. She asked,

"Bra or no bra? Do you have a preference?" I kinda like it when the girl keeps her bra on. I think it's sexy. I said,

"On" She smiled and said,

"Good choice!" Angel undid her pants and started to shimmy out of them as I was doing the same for mine. She kept her panties on too, but I was buck naked and my cock was sticking straight up from my crotch. She kicked her pants off and pounced on top me. I thought, 'This is incredible! I've never been with a girl this hot before! She's as horny as I am. Maybe even hornier!' Angel's tongue was back in my mouth and her long body was pressed against mine. She was grinding her firm tits against my chest as she thrust around in my mouth with her tongue. After a couple of minutes she broke the kiss and breathlessly said,

"Wrap you legs around me." I was so entranced with how excited she was that I didn't even hesitate. I spread my legs then hooked them around her hips and squeezed her tightly. Angel's mouth was back over mine and her tongue was working in and out between my pursed lips as she dry humped my ass. My head was spinning from the wine and it seemed to me that I could almost feel something hard through her panties. A few seconds later she stopped humping to reach down to her panties and tug at them. The whole time she continued to kiss me and rub against me. A second later my asshole was being forced open as she pushed something big and slippery inside me. I groaned in pain as my ass was forced to stretch farther and farther to accommodate what Angel was pushing into me. In the back of my mind I thought, 'I guess she got more out of Mandy than that I was just a little kinky!'

Finally my ass was stretched open far enough and I could feel the shaft of her strap-on begin to slide into me. It hurt like hell, but my groans were muffled by Angel's mouth and her own moans of pleasure. Then it dawned on me, her moans were real. She wasn't trying to sound excited about using an inanimate object as a surrogate penis, she was pushing the real thing into me! When this realization hit me my first thought was, 'Holy shit! I'm being fucked in the ass by a guy!', but then I remembered that lovely vision that had greeted me at the door just a little while ago and I had to reassess the situation. 'I'm being fucked in the ass by a girl!' As strange as it may sound that actually made it a bit easier for me to accept. I'm sure there are those of you that think I was just fooling myself, but what the hell, I don't care what you think.

She stopped pushing that hard cock into me and pulled her mouth from mine. We were both breathing hard, her from excitement and me from pain. Her face was close to mine as she said with a smile,

"My, My, but aren't you a tight one! It's going to be a lot of fun getting you stretched out so that I can easily slip into you when ever I want." I was just getting ready to reply when she started pushing again. I groaned loudly as my new girlfriend forced more of her cock into me. She stopped again and said,

"I just love entering a new boyfriend for the first time, it gets me so turned on I just want to...well..." Angel pushed hard, forcing the rest of her cock into me. I cried out again loudly as she groaned in ecstasy.

"Oh. My. God! It feels so good to finally be up to my balls in a nice tight butt! I haven't had a boyfriend for almost five months and the lack of sex has been driving me crazy!" Angel pulled back and pushed herself deep into me causing me to cry out again.

"Yea baby! I want to hear you moaning and groaning with my big girl cock buried in you! I think it's sexy as hell when my boyfriend is vocal while we're having sex! It turns me on and makes me want to screw him that much harder to make him moan even louder!" With that she pulled back and thrust hard into me. I groaned loudly and finally blurted out,

"Angel you're hurting me! You're too big, please stop!" A strained look came over Angel's face and she started grinding her cock hard against me as she squeezed me tightly against her body. She covered my mouth with hers and thrust her tongue as deep into my mouth as it would go. With a huge groan Angel exploded in my ass. Not once, but five hard shots of cum each with its own thrust and groan. She pulled her mouth off of mine and panted hard in my ear as she tried to catch her breath.

I was lying beneath her thinking, 'I just got the hell fucked out of me by my girlfriend and her cock is still inside me. If I'm truthful with myself she pretty much just raped me too.' But along with feeling her still hard cock in my ass I could also feel her round firm bra clad boobs pressed against my chest and her shapely butt under my heels. This was the same hot girl I'd been mooning over for the last few weeks. The only problem was instead of me on top of her with her legs wrapped around me, she had her cock buried in me and my legs were wrapped around her. Ok, so that's a pretty big problem.

Angel rose up so she could look in my face. She wore a lover's smile as she said,

"That was great! I haven't cum that hard in months! It's so good to have a boyfriend again!" She kissed me on the lips gently then continued, "I'm sorry if I was a little rough on you, it's just that I was so horny I could hardly wait. I wanted to jump on you the moment I opened the door to let you in! When Mandy told me you let her use a strap-on dildo on you, I knew you were the right guy for me." She started making short little thrusts with her still hard cock as she said, "This is much better than any old strap-on. Besides I'm probably bigger than the strap-on she used anyway, and bigger is better!" Angel's face grew serious as she kissed me again and said, "You're mine now. We're boyfriend and girlfriend, a couple. I can't wait to go to dances, parties, movies, picnics, study together, all those things you get to do when you're a couple!" Angel put on a sly smile and said sexily, "And don't forget about all of that sex! We're going to make love all the time! I'm going to be your best damn girlfriend ever!"

Angel sat up off of me and slipped her hands behind my knees. She pushed them up against my chest and started to slowly thrust into my ass. I watched her breasts move and sway with her thrusts. I was trying to come to grips with the fact that I was watching my hot new girlfriend's boobs bounce and sway as she fucked me with her cock. Angel reached down and took my hands and placed them on her breasts as she said,

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