Tabatha’s first time:
The thing I remember about Tabatha was what really attracted me to her was she was rather meek always quiet and kept to herself. Only God knows why, she was rather cute, at first appearance I’d say she was about five foot six, long dirty blonde hair that had a natural waviness to it. He figure would be a complete mystery because she always wore loose sweaters.
But this is really a strange thing for me, normally women come to me, this is the first time in a while that the hunted became the hunter, in my case. We had an English Lit class together, when we worked in class as groups she was always quiet only speaking when spoken to, and always doing her share and if not more of the work.
But one day it was about a month into the semester, or so, as everyone was packing up and leaving I was out the door one of the first people, which was my plain I’d wait for her to come out, ask her if she would like to get a cup of coffee sometime, nothing serious just casual, and work from there.
I stalked around in the hallway waiting for her to come out and when she did I just said to myself “Do it now or never.” She was walking down the hall, the opposite direction, and I just kind of quickly moved to catch up to her, speaking along the way. “Hey Tabatha.”
When I called out her name she stopped and turned around, pausing for a second to think. “You’re Tim right?”
“Uh yeah,” I said I could tell there was a goofy look on my face, as I was thinking how do I say this? “Um, I was wondering if you’d maybe sometime like to get a cup of coffee or something.”
“Oh,” she said as I could see her blushing a bit as she turned away from me. “I, I have to get to class.”
With those fateful words, I was left standing there. Was I shot down? Hell if I know, all I do know is at that moment I was thinking I don’t think anyone’s ever asked her something like that. Which made me think of another thing, how long has it been since I’ve had a chase like this? “I’ll be damned, the chase is on.”
I was about two days later that I finally got a response out of her, normally I’m in the class room getting ready about five minutes early or so, because I use a laptop to take my notes and need to get the juice going, to it. I was sitting there getting everything going when she walked over, to where I was sitting.
“Were, were you being serious the other day?” She asked, trying to mask the anticipation of my answer, which made me think I may have been right in thinking; she’s never had a boyfriend or anyone ask her out.
“If I wasn’t I wouldn’t have asked,” I said bluntly. I normally would add the words †˜I think you’re cute’ or †˜I really like you’, but I held my peace. I don’t really want to crush her that hard if things end up going sour. I still have a heart, though I don’t use it that much.
After class we went down to the student café I bought us some coffee, and we sat and talked about class and other things, then the big bomb gets dropped in my lap. “Why did you ask me out?”
Now this is where I’ve found it’s best to not lie, but its best not to tell the truth either. Though what few times I’ve been the one who took the indicative, I’ve learned this is that moment where it all comes down to one thing, what you say and how you say it. “Why do you think I asked you out?” I answered her question with a question of my own.
“I’m not sure that’s why I’m asking you,” she shot back, her brown eyes gazing into mine.
“Honestly,” I said pausing for a second. “I think it’s because you are always so quiet in class and you seem to shy away from people. I just felt that I wanted to get to know you.”
“And there is nothing to do with you wanting to date me so you can just get laid?”
I was taken aback by this full frontal assault. “If, and that’s a big if, it does come to that it’s not for my soul purpose of getting to know you; only an added bonus.”
“You have quite a reputation as a †˜player’ around school Tim. That’s why I ask.”
“I will be honest with you,” I said as I sipped my coffee. “That’s not a lie, but then it’s not true either. Very rarely do I actually take the lead and do this. Most of the time I go out I go with a friend or two and let them do what they do. The women just come to me. Why I don’t know, and I still try to answer that question myself. I’m a geek not the James Bond type.” That last little bit I think may have made her think I was making a joke because she was giggling a bit after I said it. That was good if I can make them laugh it’s a good thing. “But honestly I think it’s because people find out who I am, from word of mouth, and they think †˜rich boy’.”
“Are you a †˜rich boy’?” She asked as she took a sip of coffee. I don’t think she’s said this much all semester in class. It makes me wonder if I’ve cracked the shell and found what was hidden.
“Yes and no,” I answered bluntly. “I’m a trust fund kid. Not because of my parents, my grandparents on both sides set up a trust fund in my name. When I turned 18 I found out that I was worth 1.5 million. My parents almost had a heart attack when they found I donated a most of it to charities.”
“And how much is most of it?”
“One million, I kept the five hundred thousand for when I do graduate from college to start up my own business.”
I had her eating out of the palm of my hand, which kind of made me feel guilty, because I knew what was going to happen. Sooner or later we’ll have sex, I’ll get bored of her after that, and then another woman will come along, I’ll cheat on her a bit and then, she’ll find out, never want to talk to me again, and life goes on.
I couldn’t guess that the sex would be sooner than I thought because it was about an hour later we were back in my dorm room. At this point and time I’m a Resident Advisor so I actually have a dorm to myself, which I’ve made into my little pad. The RA’s room only has one bed and one desk, so it was easy to get a futon in there and an extra mini-fridge, and some other creature comforts.
We were actually sitting on the futon making out. When the though ran through my head. †˜It’s always the quiet ones.’ I loved the feeling of her tongue intertwining with mine, which pushed me even further, a trick I had picked up back when I was in high school and was messing around with my GF of the times mom, that’s another story right there. But I slowly started to move my tongue so it tickled the space behind her front teeth.
She pushed herself away from me and then looked at me perplexed. “I, I’ve never done anything like this before.” She seemed to be ashamed to admit it. “But I don’t know why, I just feel comfortable around you.”
“If you don’t want to go any further, I’ll understand.” I said with an apathetic undertone. Truth be told I wanted to plow right into her, make her scream my name.
“I, I want to.” Was all she said, when she started to unbutton the cardigan sweater she was wearing.
This was the first time I really got a good idea of her figure; she was wearing a tight fitting tank top that really defined her curvature. She had a slim build not anorexic skinny but slim, if I had to guess I’d say she had a 32-34B 30 34, which I latter found out was not far off.
“Listen,” I said honestly. “I will not lie it may or may not hurt, when we do this. Are you prepared for anything to happen?”
“I know about what may happen,” she said as she started to pull away the tank top.
I just closed my eyes and pictured god, in my mind standing there before me with women clinging to him as I gave him a thumbs up. When I opened my eye back she was standing there wearing a pair of pink panties and a matching bra. “You know you really shouldn’t hide your figure, you have an excellent body.” I grabbed a hold of her and set her down on my lap, I could feel myself getting harder, as I slowly moved my hand down into her panties, which gave me a surprise, normally when I’ve came across a virgin they always have a large quantity of pubic hair, which would grace my hands as I did this, but her snatch was smooth, as if it was freshly shaven.
I put that past me and worked my fingers around if I was going to do this I didn’t want to hurt her too much, so it would be best to get her lubed up, and aroused, before I actually did anything. Slowly I moved my hands my fingers dancing circles around her clit as I took another finger and slid it along the opening of her slit; she was starting to get a little wet. My free hand danced up in circular motions and then with the knack picked up from doing it so many times before; the bra was unhooked and fell gently to the floor.
I could hear a faint murmur of moans starting to escape her as I moved my free hand over one of her breast caressing it, and pinching the nipples, which I could feel stiffening at my touch. I then took the inactivate to give some more special treatment, my fingers that I had running along the slit of her pussy, slowly made it’s running deeper as I could feel her getting wetter, and wetter I plunged them in.
She started to stifle a cry as I started to plunge a finger slowly in, as it glided and pressed against the hymen. But she soon relaxed, and began to enjoy my finger exploration as I moved about. It felt as if my finger was being vacuumed in, as her tight hole clasped down, onto my finger, as I moved it about, slowly trying to find that one special spot. Her breathing got heavier as I moved slowly about, and then I think I may have hit the spot, as she started to moan loudly, as she contracted around my finger, and the wetness, grew greater as my hand became soaked.
My causing her to orgasm was making me harder by the minute, which took me no time to think, I moved my hand from inside her, and then pulled her off of my lap. “I hope you enjoyed that, because there will be some more pain before the pleasure really kicks in.” I took off my shirt, which really gave me away as being a geek; I spend about an hour a week total in the gym and it really does show that I don’t do much. I had a small pooch but nothing really flabby and some hair on my chest, but not a forest. But soon as the pants came down my hard on was pushing at the seams of my boxers as I pulled them away letting him spring straight to attention. I was standing there completely buff, before a girl who I was about to take her virginity from as she sat there before me in nothing but a pair of sopping wet oink panties. I walked over to my desk and rummaged through the drawer and grabbed two things, a condom from a box that was almost empty because I gave them to my residents when I notice them bringing girls to their rooms, with them. I’m not going to cock block someone who is old enough to make their own decisions but I’ll make one decision for them and that’s to keep them safe; and a little sign I always hung on the door when I either needed some privacy or was talking to one of the guys on the floor about something personal.
The sign was an easy slip onto the door, and the condom like a second skin was easily placed on my manhood as I moved her over to the bed, and pulled her panties away, and laid her down. I rubbed the head against the slit as I teased her a bit. “Do you want the pain to be intense and quickly dissipate or long and low?”
“Just do what you thing would be best,” she answered.
I told myself to start slow as I started to move myself in, I could feel the force of the hymen fighting back at me as I slowly pushed forward, I could see her gripping the sheets as the pain started to well up a bit. “Please bear with this, it will be over soon.” I thrust as hard as I could rip into her virgin hole, as she let out a yelp. I had myself buried to the hilt inside of her, and let it set there for a minute then slowly started to pump in and out trying to work the tightness in the mussels out of her and she began to accept my manhood as I started to pick up the pace, and force. The tightness, reminded me of the first time I had ever tried anal sex.
After a few minutes she was moaning loudly and contracting around myself in another orgasm this time her whole body shaking from pleasure as I gripped her and rolled so I was under her, the whole time giving her instructions, on how she needed to move and such.
It took another ten minutes and she was orgasming again and this time I let loose myself as she collapsed on top of me my still had cock, began to grow limp inside of her and I pulled away, noticing a small puddle of blood, that had congregated on the sheets, and around my manhood.
I got up and looked at the small alarm clock it was about 4pm I had a lecture in 30 minutes, I decided I was going to ditch it and forget it, there was no way I was going to leave my room. Not with a freshly deflowered virgin laying in my bed. I needed to do some damage control, before things got too out of control.
“Uh Tabatha,” I said as I pulled the condom away like a snake shedding its skin, and threw it into the rubbish bin. “The bleeding is normal and it will happen a bit throughout the rest of the day or so. I need to take a shower and you are free to join me I think we both worked up a good sweat.”
“I don’t have a change of clothes though,” she said as she looked at me.
I wanted to just say does it really matter? But I held my peace. “If you want you can borrow some of my sweats.”
It was mid November so the offer was a piratical one, which she seemed to buy, as she followed me to the in suite shower that was shared with the guys in the next room; which I poked my head in on to tell them to not come into the bathroom that was shared; which they knew as code for girls in the shower, be courteous and use the communal.
After a shower I changed the sheets off of my bed, took the books out of my bag and put her clothed in it, and then walked her back to her dorm, she took my bag up with her changed out of the sweats and came back down with the bag now with my sweats inside. She gave me a kiss, and told me she had a night class but would call me later. I just walked along back to my dorm to drop the bag off, and then went to get some dinner; before heading back running the events of the last 3 hours over in my head.