The Way It Should Be

by KinkyTwinky

What’s your gender? Genderqueer / Nonbinary
How old are you? 24
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Europe
What country and/or city do you live in? Netherlands
What’s your sexual orientation? Mostly gay/lesbian
How many sexual partners have you had in your life (including oral sex)? 80+
How many hookup stories have you here posted before? 4

The Way It Should Be

How long ago did this hookup happen? last weekend

What was your relationship status at the time? Single

How would you best classify this hookup? Start of a relationship?

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? T. is a man in his early 50s. He is bald, tall, stinging blue eyes. He is very skinny and muscular. He has sexy grey hair all over his chest.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I met T. online as both of us were looking for a relationship. I asked him whether he would like to meet me in a male or female outfit. T. chose female. So I did my best and put on hot lingerie, skirt, padded bra, lipstick, etc. My hair is long and I am small and skinny. i am very girly.

We met in a gay cafe so people did not react to my outfit in any undesirable way. T. and I were very interested in each other and chatted forever. We joked how my father is exactly the same age as T.

T. was very pleased with my outfit and told me that he loves to meet up with a girl as long as he knows that there is a boy under the clothes.

The mutual attraction was obvious and we soon started holding hands and eventually kissing. There was absolutely no reason why we should not have sex on the first date. T. proved to be very confident and asked me whether I would join him to his apartment.

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? T. proved to be a very tender lover. We french kissed for a long time on his sofa. The clothes came off and I was the boy that the man T. wanted to find under the female clothes. He enjoyed kissing and caressing my entire body, including my penis. He kissed my penis and licked my balls. It felt so sweet.

I opened T.’s pants and got his long dick out. I sucked on it extensively. T. told me he was about to cum and should stop if I wanted to experience anal pleasures. T. ‘s dick remained rock hard as he fully undressed, got his lube out and put a condom on. T. licked my anus, rubbed his dick against my entry and gently slid it in. It was a great joy indeed. T. proved to be the most gentle lover I have ever met.

Later on that evening, we took a bath together. We kissed and cuddled in the bathtub and he took me again. it was pure magic. Sunday morning, we had anal sex for a third time. T. was so gentle that my anus did not hurt. On Sunday he pulled out before cumming and I experienced the great satisfaction of T. spraying his load into my face. What more can a boy ask for?

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? I asked him whether he wants to see me again. My heart jumped with joy when T. said yes! I am in love! T. is a great, gentle lover and i believe that he has a big heart. I am happy that I may be able to leave the days of empty one night stands behind. I am in love again!

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

What were your motives for this hookup? Fun, pleasure, horniness, Attraction to partner(s), Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more

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? I have already told my mother and a few friends, they are very happy for me and hopeful that it will lead to relationship.

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? How loving and tender T. was. That I fell in love with him. That I believe that he wants me as his boyfriend.

What was the WORST thing about this hookup? Nothing

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I want to leave the world of casual sex behind me for a while and focus on what will hopefully be a new relationship.

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

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

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? Casual sex is great and necessary, but I feel the need to have a relationship to fill the void. It is easy to get sex, but hard to find love.

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