The Forward Waitress

by Tommber

What’s your gender? Man
How old are you? 54
What’s your race/ethnicity? White / Caucasian
What continent do you live on? North America
What country and/or city do you live in? Michigan
Highest education received: Some college (not currently in college)
What’s your occupation? Executive
How religious are you? Somewhat
What’s your sexual orientation? Heterosexual
Any other term(s) that describe your sexuality or sexual identity? Fun. Playful. Adventurous.
How many sexual partners have you had in your life (including oral sex)? 360+
How many hookup stories have you here posted before? 13

The Forward Waitress

How long ago did this hookup happen? Summer 1983

What was your relationship status at the time? Single

How would you best classify this hookup? First of many

How long did you know the person before this hookup? Just met that day

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? I was visiting my brother and some friends in Indianapolis, Indiana. I had been in a serious accident a year earlier that caused me to be disabled for several years during my recuperation and, since my fiancé had broken up with me partly because of my physical condition my confidence was a bit damaged as well. Fortunately I still had my sense of humor and had no problem getting people to laugh. L. was no exception.

L. was the pretty, blonde waitress where one of my buds and I went for dinner one evening. L. had an athletic type body, was 5’10” tall, weighed about 130ish, with slightly wider than average shoulders and strong hips (without being wide). Her hair was naturally semi-curly hair; she had aquamarine blues eyes; and a sweet yet very strong, almost aggressive smile, and a hearty laugh. Her eyes made her look as if she was either going to bite your head off or introduce you to something dangerously fun. She was quite outgoing and had a sweet yet somewhat tomboyish demeanor, and had just celebrated her 18th birthday a few weeks earlier, so was enjoying her first job as an adult.

When L. came to our table with waters and menus I started right in with some corny joke that got her laughing immediately. I kept on with the jokes and puns every time she came to the table. When she asked what we would like for dessert I looked at her, turned in my chair to face her directly, and said, “What time are you off work tonight?” She looked almost puzzled but told me that she would be done by 11:15. To which I replied, “I’ll be back to pick you up then and have you for dessert.” I then turned back straight in my chair while still looking at her with a smile. After a moment’s hesitation she said that she would call her brother and tell him not to pick her up.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I picked L. up at 11:15 as planned, and took her back to my brother’s place, where he lived with a couple other college guys. After the introductions we lit up a couple of joints and passed them around between about 10 people. We all joked and laughed and generally just acted like a bunch of college kids having a small party. After several had left, and the others living there started filtering out to go to bed, L. and I chatted and got to know a little about each other. Up to this point all I had done with her was talked, held her hand and let her lean on me with my arm around her shoulder after smoking a bunch of weed. After chatting for about a ½ hour, she asked me why I hadn’t tried anything with her yet (please remember I told you that my confidence had been shaken from my physical condition and my fiancé breaking up with me partly because of it). That being said, I told her that I was trying to be a gentleman. To which she replied, “Well, I appreciate that but I’m horny and want to be the dessert you promised I would be.”

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 took her chin in my hand, brought her face to mine, and kissed her deep. After making out on the sofa for a few minutes I got up and led her by the hand up the stairs to the bedroom. We made out on the bed for probably about 10 minutes before I started undoing her blouse, exposing her very ample 36D breasts with nipples about the diameter of an American nickel, and they were nearly an inch long.  Up to that point I don’t recall ever seeing or even imagining nipples that large, and I happily started teasing her nipples lightly with my fingers before kissing down her neck to her shoulders, then on to circling those magnificent breasts, slowly working my way back to her nipples. When I started flicking her nipples with my tongue and began sucking on them, L. arched her back and started a combination of moaning and purring almost like a kitten.

Because of my back brace and the way my back had been broken, I was unable to stay on my knees for very long, so I told her she was going to have to sit on my face if she wanted to really be my dessert. She quickly got up, allowing me to lie on my back, then promptly and perfectly mounted her pussy on my waiting lips and tongue, and I ate her to several convulsive orgasms before she turned around to the 69 position, and gave me a beautiful blowjob while I continued to feast on her nectarous twat.

Of course, we eventually got on to fucking in the cowgirl position, which really was the only position I could do other than doggy (because of my back brace), which we did for a while before going back to the cowgirl for me to cum inside her.

We fucked for nearly an hour before I was nearing exhaustion from not having the stamina I did before the accident a year earlier. After we were done we fell asleep in each other’s arms for several hours before she woke me up and asked me to take her home so she could wake up there.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, 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? When I took her home we set up another date for two nights later. L. and I saw each other every time I went to Indy for the next 7 months, which was every 2 to 3 weeks. We enjoyed a bunch of regular dates, most of them ending with hot sex at my brother’s place, a few times at her mother’s place (where she lived), and a number of times in the back seat of my car. We once had sex in the movie theater while watching Mr. Mom. One of the times at my brother’s place we were fucking sitting up on the sofa in the living room when my brother and a few other guys came in. I may write about that experience in a later post.

We stopped seeing each other after I made the sophomoric mistake of saying something to one of her brothers about her that I should never have said to anybody. I learned from that foolish error.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) Birth control pill / patch / ring / injection / implant

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Thought it was an important experience to have, To feel better about myself, To feel more desirable, To feel more confident, Making new friends

How intoxicated were you? Not at all (no alcohol or drugs)

How intoxicated was your partner? Not at all (no alcohol or drugs)

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? My brother and a bunch of the other guys and girls who were there, and a girl that I was seeing back home. All those who saw her and got to know her were impressed because she was not only drop dead gorgeous, but she was also intelligent and well-spoken. Their responses were somewhat varied but all positive.

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? L. was one of the prettiest women I had been with up to that point, and was just as hot for me as I was for her. The way she was bold enough to ask why I hadn’t tried anything with her yet because she knew that was why I told her what I “wanted for dessert”.

Her nipples were splendid! Outstandingly impressive even. I have rarely seen nipples like hers, even though I have had well over 350 sexual partners in my life, and seen countless porn images.

What was the WORST thing about this hookup? That she wanted to go home to finish sleeping instead of staying with me the rest of the night, especially since it was nearly 5:30 when she woke me up and asked me to take her home.

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I don’t think it changed the way I think about CS or my sexuality, but it did boost my level of confidence across the board in my life.

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

All things considered, how NEGATIVE was this experience? Not at all negative

Anything else you want to add about this hookup? This one really boosted my confidence and helped me recover emotionally from a very hard year, one in which I very nearly died and was almost paralyzed from a severely broken back, and was emotionally hurt when my fiancé dumped me in part because of my injuries. L. was exactly what I needed at that point in my life, and I will forever be grateful to her for how she helped me get back on my emotional “horse and ride again.”

What are your thoughts on casual sex more generally, the role it has played in your life, and/or its role in society? What would you like to see changed in that regard? I regard casual sex as somewhat of a necessary luxury. I have enjoyed CS since I was very young with women from nearly every walk of life, and it has been my privilege to learn from each of them how to observe and pickup on the smallest of signals indicating what a woman wants or needs during sex (mostly in 1-on-1 situations), in order provide better and more pleasure to a woman during sex, as well as outside of the “bedroom”. My thinking is that if we could somehow help others to see CS as a normal part of society, then we would see a lot of other apprehensions and inhibitions crumble.

What do you think about the Casual Sex Project? I enjoy reading the various ways people describe their sexual encounters; how they thought about their partner(s), and how they feel about their partner(s) after the encounters.

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