This is a print version of story Does the first time count? by SinSeeker from

Does the first time count?

Yet another true story of the sexcapades of SinSeeker.

I'll start off with a little bit of a physical description of myself. One of the comments on my first story mentioned that it would be better to get into more detail on the people involved and I figured I'd follow his advice, since it does sort of make sense.

Now, I'm just shy of six feet tall, and I mean only like a quarter inch shy, so I say I'm six feet. I'm about 220 pounds and built something like cross between a refridgerator, truck, gorilla, and linebacker. I remember in high school they wanted me in football and lacrosse so bad it hurt. Anyway, I'm nearsighted so I wear glasses and have shortish dirty blonde or brown hair depending on who you ask and brown eyes.

The girl in this story, we'll call her Tori because Victoria is too long and neither are her real name. She's exactly fixe feet tall, and might weigh about 90 pounds soaking wet (pun fully intended). She had good high B or low C cups, she said that it depended, but they were a good size for me to get my hands on, and that's all that mattered to me. She had good sized hips, but a small waist and legs that went all the way up to a very nice, firm ass. She had about jaw length really dark (but not black, she insisted >.>) hair and hazel eyes with an interesting dark brown rim around the hazel. I must admit, I really like nice eyes, but thankfully not to the point of fetishism, although you'll probably see me make note of eye color in other stories.

Now, on to the important bits. Sorry about the boring stuff. On to the actually interesting bits. XD

I met Tori in Starbucks one day while getting my usual Venti Green Tea Frap. She greeted me and gave me my drink as usual. We had been seeing each other in Starbucks for a while and she always remembered my name. One day while I was paying, I asked her what time she got off of work, and she told me she got out about 11 AM but had class. I inquired as to where she went to school and as luck would have it, she went to mine. She was taking a class I had already taken, and I told her that I could help her study over lunch and she happily accepted.

We set the date for early the next week. We got to talking over lunch at one of the local sports bar restaurants and getting to know each other. I practiced martial arts, worked out and painted in my spare time when I wasn't studying or working on my book (sadly, this is all true, I'm a bit of a dork XD). She told me about how she liked to read and watch movies.

Movies. I had hit the jackpot. I have a DVD collection of roughly 800 DVDs. I told her so and told her that we should do lunch at my place if her boyfriend didn't mind. She blushed a little and admitted that she didn't have a boyfriend. I asked her if she would like one, and she stuttured a bit, blushing about the deepest red I've ever seen anyone blush, and said that she would think about it. After lunch, we studied a bit, but she was still a little nervous, but she found my old notes extremely useful and agreed to meet the next day.

The next day, we met after classes and went to another place in town that I liked but she had never been to before. After ordering, we were studying a bit and when the food came, I noticed that she had difficulty making eye contact. Now, to give you a bit of background on myself, I was a psychology major before switching to another major. I analyze EVERYTHING. I immediately read signs of guilt, shame, worry, and expectancy on her face. I asked her if everything was OK, and she said that things were great.

I figured that if I pressed any further, she shoot down any of my chances, so I let it go. After a bit of studying and pointedly NOT bringing up the offer from the previous day, she approached the subject with, "You don't have a girlfriend?"

"No, not at the moment. My luck with women...isn't exactly the best. The last sorta kinda girlfriend I had kinda got me stabbed." I smiled to ease what I thought would be concern, but her eyes widened and wanted to know more. I told her the bare minimum. She was shocked and actually disappointed in the girl for lying to me like that. I asked her about previous boyfriends she had had, and she blushed again and cast her eyes downwards, admitting that not only did she not currently have a boyfriend, but had never had one.

Never had a boyfriend? This hottie? ...I think I REALLY hit the jackpot. I thought to myself. She said that I seemed like a nice guy, but she didn't know if she was ready to date. I asked her how old she was and she was almost two years older than me. I told her that it didn't have to be anything serious, just going out to dinner and such, much like the beginning of most relationships.

She reluctantly agreed.

After several study sessions, she started to see an improvement with her grade and she insisted that we meet more often if my schedule allowed. I told her that I'd make the time and we met almost every day to study and grab a bite to eat or coffee or something. We gradually grew closer, and the term was starting to draw to a close. I invited her back to my place for a movie.

She wanted to watch American Pie, which I had, and we were just chilling and watching it when I felt her hand on my leg. OK. I thought, it's no big deal, we'll see where she goes with this.

As the movie went on, I could feel her hand move slowly up and down my leg. I put an arm around her and lifted her onto my lap.

"If you have something on your mind, I'd like to hear it." I said, staring into her eyes.

She smirked, "What would you say if I told you I that when I touched myself at night, I thought of you?"

For the first time in a very long time, I didn't quite know what to say. Words not wanting to cooperate, I just smirked, reached my hand around to the back of her head and pulled her in for a long, deep kiss.

When we pulled back, she smirked too, "I thought you might say something like that, but I felt that hard on by the time our tongues touched. Is there something YOU want to say?"


"Well, what is it?" she aksed.

"I'm going to fuck you."

"You are, are you?"

"Yep, it's not up for negotiation."

"What if I say no?"

"Say it now if you are, 'cause once I start, I aint stopping until we're both done."

"Hmm.... Yes."

"I thought so." I said as I picked her up and carried her into my room.

I set her down on the bed and we started kissing as I ran my hand up the inside of her shirt and under her bra to massage her breast. She moaned softly into my mouth as our tongues met and her hips rose to meet the leg I had in between her thighs.

She reached down and started stroking my already stiff cock and when I thought I was about to burst, I pulled away from kissing her and started working on getting her pants off. She was a little hesitant and when I starting pulling her underwear down, she put her hands on mine.

She was blushing, and I couldn't tell whether it was because she was nervous or horney.

"I...I'm a virgin. Please be gentle..." she said, turning that redder than red color she had a while back.

For the second time in one day, I was at a loss for words. I mean, losing your virginity as a's a little different for us than it is for girls. You can't tell the difference, we don't have a cherry to pop. I honestly was a little worried. I'm a big guy downstairs, at eight inches, I was afraid I'd hurt her.

After looking into her beautiful eyes for a moment, I nodded. This was her first time. It deserved to be something special. She had decided that I was going to be the man that would take away her virginity.

She removed her hands from mine and I slowly pulled her underwear down. She had a little pubic hair, but I could tell that she had recently shaved. I was somewhat surprised, because this meant that she was planning this all along, unless she made it a habit of keeping only a little bit of pubic hair. Sure enough, it was really dark (not black,) brown.

I looked at her pussy and was a little nervous. I was no expert by any means, only having had sex a handful of times. I didn't want to disappoint her for her first time. I reached up and massaged her breasts while I moved my mouth closer to her pussy lips. When I was almost close enough to touch it, she laughed.

"Your breath tickles," she said, in between soft sighs and moans as I massaged her breasts.

I chuckled a bit myself, I had never thought about that.

Slowly, I slid my tongue into her pussy and she moaned loudly. I knew that I would need to get her nice an wet before I tried to stick my cock in.

Slowly, I slid my tongue up and down her pussy lips, just barely going deep enough to pass them. When I saw her clit start to show itself, I kissed it and she shuddered. I moved back down and stuck my tongue deeper this time. I made slow and rhythmic movements up and down and side to side. She reacted well, so I picked up the speed a bit, but trying to keep the same rhythm.

I must have picked up a trick or two in my sexcapades, because soon I found myself pinned in between her thighs, legs wrapped around me and her hands pulling my head deeper into her pussy.

After a few more moments of my rhythmic licking and the occassional rubbing of her clit, she came. It was a large, hip bucking orgasm. I was almost willing to bet that that was her first one.

When she finally stopped cumming and released me from her grip, I stood up and the bulg in my pants was getting more and more painful. At least when I was licking her, I could focus on something other than my raging hard on.

She was panting and she looked over to me, "That was...amazing."

I nodded and smiled sheepishly, "I try."

"Well, try some more damnit!" she said and laughed.

"I intend to, but I need to get this raging stiffy out of my pants first and grab a rubber."

She sat up with obvious effort. I never realized just how body numbing a good orgasm was for a girl. She started to fiddle with the top button of my pants and finally got it undone. She quickly undid the zipper and pulled my cock out. For a virgin, she certainly wasn't shy about this part, but she did seem much, much less experienced than the other girls I had been with up to this point.

She stroked my cock and fondled my balls and as she looked up at me she asked, "You want me to suck it?"

"Do anything you feel comfortable with."

She nodded and leaned forward, mouth open and took the head of my cock in her mouth. I almost came right there. She started sucking on the head and swirling her tongue around it while stroking the rest with her hand. She started taking more of my cock into her mouth, slowly moving her tongue around my cock. After a few moments of this, I told her I was going to cum. She pulled off of my cock and told me to cum on her face, she had always wanted to try it.

She pulled back and closed her eyes, and I jerked until I came on her. It didn't take long, I was about ready to burst as it was. I got a few shots into her mouth, but most of it landed on her cheeks. She swallowed the pit that she did get in the mouth.

She told me she was ready now and stroked my cock to make sure it was as hard as it could be. I grabbed one of my condoms (ribbed for her pleasure, anyone else notice the irony of Trojan condoms? I mean, Troy did sort of get penetrated and fall XD) and put it on.

She leaned back and spread her legs. I grabbed her by the hips and brought her a little closer to the edge of my bed. My bed isn't very tall, so I was on my knees with her legs up on my shoulders. I asked if she was ready and she nodded.

I guided my cock to her pussy lips and she gasped. I paused for a moment and checked her face. Again, she nodded, and I pushed past her pussy lips and into her pussy. I went very slow, careful not to hurt her. She was squeezing her eyes tight, but nodded every time I stopped to make sure she was OK.

I touched her cherry with my cock and paused, "This is it. If I got any deeper, I'll pop your cherry. Are you sure about this?"

She nodded and smiled, "I'll be OK. By the way, you're pretty big. Are most guys your size?"

I chuckled, "I don't make it a habit to size up other guys, but I'm a little bigger than average."

She nodded again and I pushed through her cherry. She squeezed her eyes tight and tried not to make noise, but a little moan escaped. I looked at her again and again she nodded.

I looked at her and smiled, "It all gets easier from here. Just relax and let me inside. It'll hurt at first, but it'll get better."

She laid back and I went deeper inside. Slowly and rhythmically, I went deeper and deeper. She moaned a bit, but insisted that it felt good. She told me to move faster, so I did, but not too much. She was so tight, I thought I'd cum any minute, but I didn't let myself get too carried away. I was tempted to go balls deep, but I didn't think that she would be able to handle that on her first time.

Afer a few minutes, she was moaning in both pleasure and pain and insisted that I go faster. I put my hands on her hips and pulled her into my as I thrust forward, and I could feel her hips move into me as well. She came again and so did I.

She was tired and sore, so I pulled out and disposed of the condom and helped her to clean herself up a bit. She wasn't bleeding too much, which was good. After getting dressed again and cleaned up the rest of the way, I drove her home. She told me that she was sore, but would call me again to study the next day. She told me that she enjoyed her first time and wished that we could do this again in the future. I told her that I'd be happy to.

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