My first time

The first time i had sex was freshman year of college. So i guess that would make me 18. However before i go on with that story i need to say that while i was in high school i was in a long term relationship with a girl who wanted to saver herself for marriage ... and she also made comments that she was scared to even try to enter my penis into her vag. So we just did a lot of oral play. By a lot, i mean several times a week.

Now in college i had trouble getting my confidence up to get with a girl but eventually i started seeing girl... This girl had told me that she had alot of experience in bed. That she had "100 boyfriends" through highschool but she quickly commented that she didn't have sex with more than 10 of them though ..... Meanwhile while i knew her during college i knew her to make lots of random hookups with guys too....

Now let me be clear, i didn't go after this girl thinking she would be a quick lay. if i wanted that, i'm sure i could have gotten drunk with her, and gotten a 1 nighter. I in fact really liked this girl. But from all she, and all i knew from her I was certain of 1 thing ... i would use a condom with her.....

The first time she felt my size was slightly amusing. We were at her house, and we had been making out, and dry humping with all our clothes on ( which i don't like cause it's hard to feel anything if we are both wearing jeans. maybe if we wearing alot less clothing ... preferably none .) She went to "feel" me over my pants... she didn't feel a bulge in the usual place i guess. She asked if something was wrong... i said no, and i told her that i have my little guy go down the pants leg. She felt on the pants leg, and her eyes kind of went big.

She then did this walking motion with her fingers to see if she can figure out how big i was. We made out a little bit more, however we couldn't have sex because her parents were home.

We met up the next day during the day. It was the weekend, and we went to my dorm room. My roommate was gone for the weekend. We started doing the usual things. Making out, necking, groping. We started getting naked, and then i offered to go down on her. (something that i genuinely enjoy doing) she rejected because she informed me that, she would then feel obligated to go down on me. And she only knew how to deep throat as her method and didn't know if she would be able to do that. So we moved straight to sex. ...

My first time, started off with putting on a regular condom. And anyone with a thick penis like me will tell you... it's not easy. However i had practice putting on condoms before, and i knew the only way is to roll it on even though it feels like it's cutting the blood flow to the penis.

Once it was on, i went to go stick it in... and of course i missed. She then jokingly went "let me teach you about the vagina" at which point i was annoyed/ embarrassed so i just jammed my penis in (only got 1/4 of it in on first thrust).... that made her roll her eyes back and stop her wise crackings. After about 45 seconds or so i got all the way in and she felt my pubic bone on hers. She quickly looked straight down and said "oh my god , are you all the way in?" I said confused "um yeah?"

About 15 second later she came. Now i would like to think i know when i girl orgasms however this case it was blatant that she had orgasmed. She evidently was a squirter. I had seem them in porns throughout my younger years. So i wasn't too surprised. (i feel that if i hadn't known this that some people would have been scared their girl was peeing) I just responded with "should i keep going", which she only grunted and shook her head up and down.

After a couple more minutes of penetration, i was looking for any feeling with the condom, and i found none. The condom was too tight especially near the base where the little ring is. The girl at around the 5 minute mark had come maybe 6 or 7 times or so. My bed was DRENCHED where she was laying.

She then asked "are you going to come" i said, "the condom is too tight, i can't feel a thing really. sorry" She kind of wimpered a bit and said, "oh god, i want you to feel what i'm feeling. It's so amazing. " We went for a little bit longer.

After about 10 minutes she said she couldn't take it anymore. So i stopped. She went to go to the bathroom and almost fell down cause she said her legs were so shaky. When she got back, she wanted to hop in the shower. So we went into my dorm shower together. It was a tight fit but we manged. lol

In the shower we washed each other down. She went down and tried to get my cock down her throat.... she tried for a couple of seconds, and she only got 3/4s of the way down. She said, sorry i can't do it. And then finished our shower, and she went to go to work.

So in the end this "very experienced" girl left me with blue balls, and a very drenched bed. After that day, our "relationship" only consisted of her trying to have sex with my penis rather than being with me ... it didn't last much longer than 2-3 weeks total.

Comments

Blog entry information

Author
denton85
Read time
4 min read
Views
347
Comments
1
Last update

More entries in General

More entries from denton85

  • Drunk
    So as we all know, the best way to start any post of any kind...
  • in the city
    I guess I've gone to the city enough times from all the drunken...
  • It's nice, but can be annoying.
    The Set Up When i was in highschool i weighed probably 60 pounds...
  • ARG!
    My girl has been trying to balance a full time job, and part time...
  • Vibrating Ring
    My girl pulled out an old condom box that we had bought a while back...

Share this entry