Fun With The Kindergarten Teacher

by Steve

What’s your gender? Man
How old are you? 52
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Palm Springs
Highest education received: College degree (eg., BA, BS)
What’s your occupation? RN
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? A little
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 50+
How many hookup stories have you here posted before? about 10

Fun With The Kindergarten Teacher

How long ago did this hookup happen? 15 years

What was your relationship status at the time? Dating casually

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? For less than a year

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? We will call her teach. Teach was a regular in a chat room that I frequented. We sometimes went to instant message to talk but usually just talked in the chat room. Our chatting rarely led to anything sexual but once in a while we would flirt and get explicit with each other. Teach was a couple of years older than me, about 5 foot 5 inches, attractive, flat belly, nice ass, HUGE tits, probably about a 38 E, nice big nipples, dark areola. We were going to be at the same chat room gathering in Denver for the weekend. We had not talked about hooking up at the gathering. Several of us were at the bar drinking when Teach showed up. Most of us had been there for a day when she showed up. I had already had a hook up with another lady there the day before but that’s for another story.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We were all sitting at the bar having drinks and talking. I was looking at the other ladies there and trying to decide who I could hook up with for the night. Teach walked in looking stunning, her top two buttons on her blouse unbuttoned and her huge cleavage on full display. I couldn’t take my eyes off her tits. A few of us started doing Yaegermeister shots. About the third shot, Teach looked a little green and went outside. I followed the tits. She wasn’t throwing up but she was close, I had brought a cool towel with me and applied it to the back of her neck. She leaned into me and I held her so she wouldn’t fall down. I felt her hand stroking my soft cock which quickly became firm. She said I want you. I want you to fuck me. Who was I to argue? I told her my room number and to meet me there in 30 minutes. I went back in, told the that teach was a little better but to keep an eye on her and that I was going to bed. I went to my room, showered, put a towel around me and waited. About 5 minutes later there was a knock at the door

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? I opened the door and Teach came in. We made out standing at the door. She pulled my towel off and got down on her knees and began to suck. Very nice technique, pulling on my balls, sucking the head, licking the shaft, sucking my balls. I stood her up and led her to the bed. I straddled her chest and began to stroke my cock in and out of her mouth. I slid down a little and slid my cock between those magnificent tits. She shoved them together and I began to stroke between them, her licking the head of my cock with each stroke towards her mouth. I stroked her tits, reached around and played with her clit. I slid down between her thighs and buried my face between them, lapping at her pussy and clit. She began to squirt like I had never seen before. When she got done squirting I got up and grabbed all the towels from the bathroom and kind of made a dam around her crotch. I resumed eating her pussy and she resumed squirting, the towels were drenched, I pulled the bed covers down to absorb some more. I finally spread her legs and put her legs on my shoulders and slid into her. She was not real tight but tight enough to make it very pleasurable. With the amount of alcohol that I had drunk, I didn’t have whiskey dick but I knew I wasn’t going to cum soon. I stroked and stroked and slammed into her, my balls slapping against her ass as I sucked her nipples. She squirted several more times when I would pull my cock back out. I was out of towels and bed sheets. I finally felt my balls tightening up and I loaded her pussy up with cum. I rolled off exhausted. I laid there for about 5 minutes and noticed that I was getting hard again. I sat up, she was laying on her back with her knees up. I asked her if she was ready for another go. She asked if I had taken a Viagra or something, I just told her, no, that’s just me. She spread her knees and said, “Fuck Me.” I climbed between her knees, placed her ankles on my shoulders and began to long stroke her. I built up speed and began pounding her sweet pussy. I wasn’t sure if I could cum again or not, but her pussy felt so good around my cock I was going to go until I couldn’t go anymore. I probably stroked her 10 or 15 minutes, she finally said, stop, I can’t take anymore. She had to have cum 5 or 6 times. I said… “just a little more, I’m almost there”. She said ok. I renewed my efforts and about 2 minutes later I unloaded deep inside of her. We got up, showered, and she said she was going to go to bed. I tried to talk her into staying a little more but she said she had to go.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

Did your partner have an orgasm? Yes, multiple

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? She left. I called room service and told them I had spilled a drink on my bed and could they come up and change the sheets and bring more towels. I went back downstairs to where the group was in the bar and proceeded to talk one of the other ladies to come up to my room, but that’s another story

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Sterilization

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Thought it was an important experience to have, Intoxication, Power / Dominance, Making new friends, Didn’t want to disappoint my partner, It was easy / convenient

How intoxicated were you? Drunk/high but not wasted

What substances did you consume? Alcohol

How intoxicated was your partner? Drunk/high but not wasted

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Very

Did you consent to this hookup at the time? I gave enthusiastic consent

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? one of the other ladies asked me about it afterward, she had noticed that we had both disappeared. She was happy for us. She and I ended up hooking up the next day

How would you best summarize people’s reactions about this hookup? Relatively positive

Did you get emotionally hurt as a result of this hookup? Not at all

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? experiencing someone that squirted as much as she did, great tits, good blowjob, great sex

What was the WORST thing about this hookup? she left too soon, but I hooked up with someone else later that night

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? no

All things considered, how POSITIVE was this experience? Very positive

All things considered, how NEGATIVE was this experience? A little negative

Anything else you want to add about this hookup? this was a great weekend. I go to these gatherings to get laid. There are usually 20 to 30 people there, 20 to 25 females the rest males, everyone that wants to get laid does

You have a hookup story to share? Submit it here!