Chapter 1: A shy sophomore loses his virginity to a coed with a secret
Note to Readers: This is my first attempt at creative writing as well as my first submission to Literotica. I am grateful to Chris6160 for the many hours of editing and valuable advice he has personally given me. He has enabled me to put a finished quality on these chapters.
Also note: All characters and names are entirely fictional, with the exception of Boston and Salem Massachusetts which are real when I last checked. The characters themselves are all over the age of 18.
Chapter 1: A shy sophomore loses his virginity to a coed with a secret
It all started on that first date with Molly. Oh sure, movies are filled with stories about a guy who meets a girl who changes his life, but how often do you read a story about a girl who changes what a guy believes or what a guy looks like? Molly did all of that, and much more.
Perhaps I should start closer to the beginning.
My name is Thomas Ward, but everyone calls me Tom. Except my roommate Peter. Oh, and my crew coach. I'm a sophomore in a private college in upstate New York where a lot of rich kids get a good education and a prestigious diploma. I'm not one of those kids. I got in on a scholarship and a grant from the college, one of the few grants the college gives out. That's the good news.
The bad news is that I am socially out of my league. I can't afford the expensive clothes and fancy foreign cars that most of the guys here have. My wardrobe consists mostly of jeans, tee shirts and hoodies; and I don't own a car.
Like the guys, most of the girls come from wealthy families. They wear expensive jewelry, designer clothes and drive expensive cars. Since I can barely afford to eat out at a restaurant myself, how can I take one of those girls out to dinner? Ever hear of a guy taking a girl on a date in the college dining hall? It didn't happen with me, either.
So, it should come as no surprise that by early October, I was still a virgin.
It wasn't that I didn't try. I joined the rowing team as a freshman, hoping that it would build my confidence and my physique to overcome my shyness and attract women. I'm happy to say my body was starting to look pretty good, but I couldn't overcome my shyness and lack of money. There were nights when I would fantasize about a one-night stand with a girl, but I guess I'm not the kind of guy that can separate sex from a relationship, even a casual one.
My best friend and roommate Peter tried to come to my rescue. I met Peter Warren during freshman orientation. The college assigned us to share a room based on the alphabet. Ward followed by Warren. Our personalities just seemed to click, and we decided to stay roommates in our sophomore year. It was Peter who suggested I join the rowing team.
But, unlike me, Peter is at ease with beautiful girls. His folks were wealthy and sent him to a private prep school. That's where he first learned to row. It's also where he met a lot of pretty girls who were attracted to his good looks and self-assurance. During our freshman year, he would bring girls over at least twice a week, forcing me to sleep on the couch in the lounge. From the sounds I heard outside the door, he was fucking their brains out. Those were usually the nights I would fantasize about one-night stands.
Peter is comfortable with casual sex. If a woman just wants to fuck, that is more than okay with him. He'd even remember to ask them their name from time to time. That is until the end of our freshman year when he met Heather.
Heather Cox is arguably the most beautiful girl on campus. That's saying a lot, considering the number of attractive girls here. She could easily be one of the girls in Sports Illustrious' swimsuit issue, if for nothing else than she's got the body for it and she's on the college swim team. Her specialty is the "fly," or butterfly stroke, which requires a strong core and upper body strength. Her body reflects that athleticism characterized by muscular, broad shoulders, six-pack abs, a firm muscular butt, and well-toned legs. Relatively speaking, her breasts are large for a swimmer. Peter told me she was a 34 D cup. I know nothing about breast measurements, but I do know how difficult it is to maintain eye contact with Heather when Peter brought her into our dorm room. After meeting Heather, Peter no longer engages in casual sex - except with Heather.
When Peter told Heather I was still a virgin, the two of them conspired to do something about it. That's when Heather asked Molly, one of her teammates on the swim team if she was interested in going out on a date with me. Molly agreed.
Peter and Heather made sure we had a chance to meet each other before the actual date. The first time was at one of the dorm mixers in early October. Molly was chatting with Heather when Peter dragged me over to meet her. There was something about her that attracted me to her right away. She has a slim, athletic build. Heather said she was the best free style swimmer on the team. She looked muscular in a feminine sort of way. Her brown hair was in a long pixie cut and she reminded me of a young Anne Hathaway. I found her to be terminally cute with her green eyes and mischievous smile.
A few days later the four of us had supper together in the dining hall. We mostly talked about swimming and rowing. That's when Molly noticed how calloused my hands were. I explained that oarsmen tend to develop callouses after many hours of pulling on a wooden oar for hours at a time every day at practice.
"Peter's hands are the same way," Heather winked at Molly.
"Yeah, Ward," Peter said. "She likes it when I play with her boobs."
It was during that supper when we decided on the day for our dinner date, which was tonight. Peter recommended a Thai restaurant in town. He said the food was good and the price was reasonable. I just wasn't sure whether he meant reasonable by his standards or mine.
Peter must have told everyone on the rowing team about my date. They all knew I was a virgin, and they would give me shit about it every chance they got. Most of the comments were pretty rude and only made me more nervous about meeting Molly for dinner.
For the first time in my life, I was worried about what to wear. Like I said, my wardrobe was limited, mostly jeans, tee shirts and a few flannel shirts. I did have a blazer, but nothing decent to wear under it.
"I'll lend you one of my dress shirts," Peter said as I was shaving. "I don't think any of my pants would fit you."
I ended up wearing my best pair of jeans, Peter's dress shirt and the blazer. It wasn't a bad combination, but was it good enough for a first date?
I arrived outside Molly's dorm with a few minutes to spare, as I hoped. My anxiety was building as I waited. I felt like everyone who passed by looked at me like some loser standing outside the girl's dorm waiting for a date. With the way I was dressed, the fact that I was waiting for a date couldn't be more obvious.
"Tom?"
I jumped. When I turned around, there was Molly standing right behind me. She seemed to materialize out of nowhere. I didn't see her come out of the dorm.
Molly looked great. She wore a blue dress with a floral pattern that complemented her emerald-green eyes. She had a white sweater slung over her shoulders. If she was wearing make-up, it was hard to tell. I thought her face was beautiful as it was. She might have been wearing lip gloss as her lips had a sheen to them.
One of the many things that attracted me to Molly is the way she carried herself. She was self-confident without being arrogant. She seemed comfortable in her body. Maybe she got that from swimming. She certainly got those legs from swimming. They were well-toned and muscular. So was her butt, from what little I could see from her dress. I imagine swimming did that for her as well.
"Sorry, I didn't mean to startle you. I just had to pick up something from the bookstore before our date. Are you okay?"
I answered her nervously.
"Y-y -you look lovely."
She gave me a warm smile.
"Thanks, you look nice too."
That helped me regain some of my composure.
"Are you hungry? I hope you like Thai food."
"Yes to both questions. I love Thai food. Besides, Heather already told me that Peter recommended the Thai place."
"Yeah, well about that. Peter's a great guy and all, but sometimes I think he can go too far."
"Perhaps," she said. "Do you eat Thai food very often?
"This is going to sound embarrassing, but I've never had it."
"No? Well, let me guide you. It looks like this is going to be a night of firsts for you!"
The restaurant might have been a disaster if Molly hadn't rescued me from myself. I felt so awkward and out of place. I had no idea what to do or what to order. Molly recommended I try a green curry dish, mildly spiced, while she ordered a medium-spiced Pad Thai.
At one point she offered me a taste of her Pad Thai. Since I seemed to be handling the curry well enough, I thought I'd try it. I mean, how bad could medium spice be? Four glasses of water and a glass of milk later, my eyes stopped watering and I was beginning to feel sensations on my lips and tongue again. Molly couldn't stop laughing. She had to wipe a few tears away herself, but hers were from laughter.
"Tom, I wish you could have seen the look on your face when the spices kicked in. I'm sorry for laughing, but I just couldn't help myself."
"That's okay." (I don't know if I was flushed from embarrassment or from the spices.) "I came to college thinking this would be a good opportunity to challenge myself in different ways. I need to get out of my comfort zone and try new things. Maybe that's why I joined the crew team. And maybe that's why..."
I stopped in mid-sentence. I didn't want her to know how far out of my comfort zone this date was for me.
"Why what?" Molly asked. "What were you going to say?"
"Nothing. It's not important." I stared down at the table.
"Tom, I'm glad you agreed to take me to dinner with you, too. You're so sweet." She reached across the table and held my arm.
There was something about that first time Molly touched me. It felt like something inside me woke up, as strange as that sounds. At first, I thought it might have been something she said, but now I'm sure something happened when she touched my arm. It felt like some sort of turning point for me. I felt more relaxed and more comfortable with myself. I think Molly felt something, too, because she had a strange look on her face and looked down at my arm, before looking back up at me.
I looked at her curiously trying to read into those emerald-green eyes. She finished the sentence I didn't want to say. It felt like she was able to read my thoughts.
"Molly, I think you're the sweet one."
The rest of the dinner went well. We literally talked for hours, but it felt like we had just sat down. Initially, we talked about Peter and Heather. Molly said that she and Heather were close friends through the swim team. But gradually the conversation came around to each other.
I told her I thought I might have been adopted, since I look so different from my parents and younger brother, but that was something my parents never talked about. Eventually I confessed my shyness around girls, mostly because of some malicious teasing I received from some of the cheerleaders at my high school.
"Why were they teasing you?" Molly seemed genuinely interest in the details.
