My university roommate, Rob, is amazing at hooking up with girls. He is not super handsome or anything but he has some mysterious ability to spot a willing, hot girl and end up bedding her in no time. My situation is the opposite. I'm shy around girls and was a virgin until the last month of high school. Even then, I lost my virginity to the loosest tart in school who had likely screwed every player on my basketball team. I felt used after she rode me for a quickie in a back bedroom at a teammates party. Hell, she just stripped off her panties, left her party dress on and pulled off my pants before doing it. I didn't even get to feel her breasts before it was over. The orgasm was epic and the event is my go-to fantasy to get off when I jerk off. But I want more and better.
It's not that I'm weak. I play in the university basketball inter-mural league. My tryout for the varsity team didn't workout. But I was a star on my high school team before coming here. I'm six-foot-six and was pretty awkward growing up. That's likely why I am shy around girls. Rob keeps telling me the girls would love to be with me if I just got more confident. Tonight, he says he will teach me a lesson in being the man. His new girlfriend has a roommate from the Mid-West that is not very experienced around people of the opposite sex either. She wants to get more comfortable around men now that she is away from home. Sounds a lot like me. Rob says it's a slam dunk for me to get laid. His girlfriend told him in confidence that her roommate agreed to have sex tonight. I just have to be the man and go get it.
The plan was for us to meet at our favorite off-campus pub for a few beers and the go back to their dorm room for some sex-play. Rob loves to show off by bringing girls back to our room and screwing them when I'm in the other bed pretending to be asleep. I don't feel comfortable have sex tonight with him and his girlfriend in the room. But, if that what it takes, I'll do it. Rob keeps pumping up my ego as we walk over to the bar.
"This girl is really cute, Brent. Izzy, showed her a picture of you and she liked your ugly face. Dickhead, it's all set up for you to get it on. She is super shy and will need your firm hand to get to the promised land. Izzy tells me she isn't a virgin but hasn't had much sex. Of course, she said she sucks cock, like all girls nowadays. Then again, these girls exaggerate between themselves. Who the fuck knows? It's up to you to find the truth. Are you up for this, big fella?"
"Yes, man. It's all good. Thanks for setting this up. I owe you."
The girls are at the bar drinking beer when we go in. I had seen Izzy, Rob's girlfriend, getting laid in the next bed so I know the girl beside her is my date. She is so very cute and tiny, barely five foot but with a perfect body. She has such a sweet, shy smile as she looks up at me. I smile back as confidently as I can. She looks down shyly. Izzy has on a tight party dress that barely is long enough to hide her panties and her breasts are spilling out. That's Rob's kind of woman. My blind date has a classy, yellow summer dress with a hem, modestly down to her knees. She looks amazing with her matching long, blonde hair. These girls are like opposites. As I go up to her, she looks up with her sweet, wholesome, pretty face.
"Hi, I'm Brent. Great to meet you."
"I'm Elizabeth but friends call me Bessy."
"Bessy. That's a great name."
We shake hands awkwardly. I order a beer and I sit on a barstool beside her.
"What year are you in?"
"I'm a freshman. You?"
"Same. Are you from around here?"
"No, I'm from South Dakota. Lizzy is from New York and we got placed in the dorm together. She is really something."
"Yes, I've met her a few times. I'm from Chicago."
I can't help staring at her cleavage and we both blush when she catches me looking there. There is a sexual tension between us because we both know where this is heading. Behind Bessy, Rob is laughing loudly, and he has his hand groping her tight ass. He doesn't care about Bessy and I seeing this.
Rob told me to do very little small talk and move into more sexy topics. He said this is a booty call not a relationship.
"I love your dress. It's very attractive."
"Thanks. I didn't bring too many dresses, mainly just jeans. My mother would kill me if she saw me in a dress like Izzy's. Wow."
"I hear you. I like your dress much more. It's classy."
"Thanks. Boy Brent, you are very tall."
"Yes, six-foot-six. Is that okay?"
"Sure, girls like to be with tall guys."
I feel we are making a connection and moving in the right direction. Rob comes over and stands beside us.
"I don't know about you guys, but Lizzy and I don't want to pay the high prices for beers here. She wants us to go to back to her place and drink her beer. Come with us. That's all-good Bessy, right?"
"Sure, it's all good."
"Great! Brent, pay for our beers. I forgot my wallet. Ha Ha."
We are soon out into the cool night air, walking towards the university dorm buildings. Rob and Izzy are talking a mile a minute as we walk along behind them. Bessy and I are quiet in a thoughtful way. I suspect she is as nervous as me about what will happen when we get there.
"Brent, is it okay if we go to your dorm room? I'd like some privacy when we are together."
"Sure Bessy. I'd like that better too." I shout to the others, "Bessy and I are going to my place. You guys have fun." They laugh and wave as we walk off in a different direction under the streetlights. I take her hand and we walk in silence. She is so tiny walking beside me. I hope she can take the size of my cock. It's not huge but it's in proportion to my height. I wonder if a girl's pussy is small in proportion to their height? I guess we will see soon.
"Brent, I bet you had lots of girlfriends back in Chicago. You are a very attractive guy."
"I had my share." I say lying. "And you are very attractive."
"Thanks Brent, but if you're saying that means I was with lots of guys, that wasn't the case. I'm kind of a nerd and studied hard to get my scholarship. It's good to be in university now and get some freedom." We are passing a small park. "Brent, is it okay if we sit in the park for a while before going up to your room?"