Where it happened: Her then-fiance's house
Langauge: English
Sex: Male
Rating: 5
Category: Straight
My actual “first time” happened when I was 19 — in August 1994.
But it was one of those experiences you’d rather not remember.
I won’t talk about it, but my “real first time” happened the morning
after Halloween 1995. I’ll never forget it.
I turned 21 in September, and the one woman I wanted to be with
stood me up because she “had too much homework to do, and Monday
nights aren’t good for me.” So I wasn’t feeling too great for a
few weeks afterward. But on Halloween night, I got what I deserved.
Here’s how it happened:
After I came home from classes at the U of Arizona, I took a
shower, got really stoned, and took the bus to go downtown. I got off
at the wrong stop, and walked to Carlos Murphy’s where I would meet
up with some friends to go to the Steve Miller Concert at the
Tucson Convention Center. I proceeded to get drunk and eat some
mexican food for about an hour or two. Then we walked over to
the TCC.
While we were in the concourse waiting for other people to show up.
(I was really drunk, so I’m not sure exactly WHY we were there).
I’m sitting on a table, and an engaged couple we knew walked in.
The guy was wearing his old Air Force uniform, but with fake blood
and bullet holes to make him look like a disgruntled postal worker.
The woman was wearing a “Pirate Wench Costume” with black fishnet
stockings, a vest, boots, etc. A definitely sexy outfit.
I had met the lady a couple times before, and we knew each other by name,
but that was it. We started to talk. I’d told her that this was only my third rock
concert. She told her fiance this and said “He’s a puppy! This is only his third concert!”.
We were talking still, and, totally unexpectedly, she stuck
her tongue in my mouth, and we started to make out like teenagers. This had
never happened to me before. I loved every second of it.
Then the show started. We sat in adjacent seats, but her fiance didn’t sit
near us. Still raging drunk, the concert in full swing, we made out for hours.
It was great. Not only did she “attack” me, she “attacked” six other people!!
I was so drunk it was hilarious!! With Halloween being on a Tuesday night, I had
no classes the next day. I told her this and she said “I’m really glad you don’t
have any school tomorrow.” She’d asked me how many women I’d been with and I said,
“Just one.” She was shocked. We necked and petted, and
I told her “I want you to fuck me like the virgin I almost am!” She was really pleased
to hear this request. I’d never been so sexually charged in my life. I KNEW I was going
to get laid either that night or the next day, and NOTHING was going to stop me.
Anyway, the concert ended, and I hooked up with her and the fiance. We went to
a bar/restaurant and I watched them sing karayoke. She sung Lita Ford’s “Kiss me Deadly”.
She did really well. Afterwards, we left the restaurant, and went to her and her
fiance’s house. She set me up in her 5-year old daughter’s bedroom. Her kid was staying with
her grandmother or something. I kissed my “date” goodnight and said, “I can’t wait until tomorrow.”
Around 7:30 AM, she came into the bedroom wearing nothing but a flannel shirt and panties. I was in awe.
She said, “Did I wake you?” Of course I said no. She then freed her breasts which were small, but not too
small. I invited her on the bed. We started kissing, and I got hard. I played with her tits, sucked on her
nipples. I took my briefs off, and my dick sprang out. She smiled. If I remember correctly, I then said to her
“I wanna unwrap this present and see what’s inside.” I was referring to her pussy. She took her panties off,
and I went down on a woman for the first time, though I
lied and said I’d been with one other person.
She was amazed. She couldn’t believe I’d been with only one other woman. I loved it. Eating her out felt
totally natural to me. After all, I’d read enough on the subject and seen enough porno movies to have a
good idea of what to do. I was rewarded with her orgasm.
She put a condom on me, and I layed down on top of her, and slid inside her. She moaned. I asked if she was wet enough,
and she said yes. I started thrusting, making her moan. But I was getting too much friction to fully enjoy it. After a while I pulled out,
and she said to me “Do me doggy.” I entered her from behind, and she lay flat on her stomach. She was moaning
as I fucked her doggy style on her daughter’s bed.
Then, a very scary thing happened. Her fiance walked in on us!! I was so scared, I covered myself up
and said, “Hey how ya doing?!” He looked at her and said, “Awww. Can’t I get some too?” She said, “Sure, come
on in.” Before I knew it, I was eating her out while she was sucking off her fiance!! I was losing my virginity
in a threesome with an engaged couple!!! After a moment I really started to get into it. I licked her pussy from
below while she gave her fiance head.
After about 15 minutes, she said, “You like it down there?” I said through her pussy, “Uh huh.” She moaned and said,
“Awwww. Can we keep him? He’s already housebroken!!” I couldn’t believe it. She then told me that “We’re gonna have breakfast”
Before we left the bedroom, I just had to say, “If it doesn’t get all over the place, it doesn’t belong in your face!” They
laughed a little bit.
She cooked us pork chorizo and eggs. Very good. I then waited for almost three hours before he finally went off to work,
but not before asking me where I lived. She said,”He’s staying here to help me with housework!!” I nodded in agreement.
Around 11 AM, her hungover fiance went to his job, and we “went to work” but this time in their bedroom on their waterbed.
We took our clothes off, and I immediately went down on her. After a couple minutes she said, “Wanna 69?” I was almost speechless.
She was sucking my dick as I pleasured her lovely pussy. There was no smell or taste which made me really happy. Clean girls rule!!
I could tell she shaved it because there was a little stubble at the top of her pussy.
After a minute or so, she surprized me by stopping and “sitting on it” — without a condom on me!! I was so aroused and amazed I didn’t
think anything of it. I thought, she’s a mother, she can’t have any diseases, which is totally stupid thinking. Anyway, we started fucking,
and her fiance called us like 4 times while we were fucking to see how we were doing with the housework. That was totally frustrating!!! He
KNEW I was fucking her. He just wanted to frustrate us. After the last call, I was on top of her, fucking her with all my 21 year old body had.
She came a few times, and it was such a turn on for me to know that I was the one giving her these orgasms. She said, “Uhhh! Jab that thing in me!!”
Around Noon, I was still thrusting away wondering if I was ever going to come. I’d read in the Playboy advisor that if you do the “in and out” instead
of staying in deep, you’ll get more stimulation that way. So I did this, and I finally came after over an hour of fucking. I pulled out and came on
her stomach. She wiped it around and it SMELLED.
We then took a shower together, my hard dick bumping into her at every opportunity. We then had lunch and watched some porno scenes. After about a half-hour,
she said, “You ready for another round?” I sure as Hell was!! So we started fucking like before, still without protection. At around 1:30, a weird thing happened.
As I was thrusting away on top of her, she yelled, “Oh baby, stop, baby, stop!! I’ve got cramps big time!” She then passed out and was sleeping. I was stunned
in disbelief, and wondering what to do, so we slept for a half-hour or so. We woke up later, did the housework we were supposed to be doing, and around 3 PM or so,
her fiance came home. Soon we got into their car, and they drove me home. I thanked them for the good time.
Later that evening, I went to work, came home, and bragged about it to my friends, who were shocked and happy that I had finally lost my virginity.
But, the guilt and fear soon set in. The following Valentine’s Day, I went and got an anonymous HIV test, and, thank my lucky stars, it came out
negative. I swear that if I keep taking crazy chances, my luck will run out and I WILL be VERY SORRY. So, the moral of the story is, protect yourself,
protect your parter, whether you love him/her or not.
If I saw her today, I’d tell her that she really was my first, and that I was really scared afterwards about getting HIV.
Sure, she was ugly, but not that ugly to me. I’m very thankful that she went all the way with me.
Sometimes I miss her. That was almost two years ago. I’m very fond of that experience, even though
I came only once the entire day. The woman’s pleasure is more important to me than my own.
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