First Time Anal

by anni

Gender: Female
Age: 21
Race/ethnicity: Hispanic
Current location: Florida USA
Highest education received: Some college (not currently in college)
Occupation: Entrepreneur
Relationship status: In a relationship
Religious affiliation: Catholic
How religious are you? Somewhat
Sexual orientation: Heterosexual
How many sexual partners have you had in your life (including oral sex)? 2
How many hookup stories have you here posted before? 3

First Time Anal

How long ago did this hookup happen? January 2015

How would you best classify this hookup (e.g., one-night stand, fuck-buddies, friends-with-benefits, booty call, sex with an ex, short fling; paid sex…)? Friends with benefits

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? He is my casual sex partner. The one i have talked about before. To my eyes he is  A handsome cowboy with a farmer’s tan. We have been having sex for 3 years now. He is in his late 30s. His physical appearance is nothing like that of those fake cowboys from calendars. In the years we’ve known each other i have seen him grow older. We are somehow related, we share some family so that has always been in the way.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? He texted me saying he was in town and that he would love to see me (i was surprised!). Like always my attraction to him is so vast, i couldn’t decline So i told him i would love to. We texted for days about how bad he wanted me and how much he missed me. I had totally forgotten about him, but how could i say no to a cowboy like him! So we planned to see each other a few times but it did not happen.we was so turned on that we ended up talking about anal sex. He wanted it and i knew for a fact it was painful, but i wanted him to have the experience and wanted him to cum in my butt. He said we would at least have a quickie that night, truth is i hate quickies because that is all my boyfriend can give me. Very selfish since he just cums and i don’t even get to orgasm. Back to the cowboy well i told him sure we will have it that way. So i drove to the ranch picked him up and then we crossed a fence  to the ranch next door. Once on the other side i told him “nobody is here right?” “Nah, come on” he pulled me by my hand and under a roof next to the stables we began to kiss.

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? We kept on kissing while i took his ball cap and placed it on my head. Afterwards i gave him a blow job and swallowed his load of cum He then penetrated inside my vagina making me reach orgasm with thag big cock of his. Once very wet he said can i fuck you from behind. We got on doggy style and … we fucked anal for the very first time. No need for lubricant i was super wet. He went hard,both of us moaning from pleasure. While on the other ranch they were singing happy birthday and cutting the cake. In my head i laughed this was the second time we fucked while there was a birthday going on. Minutes later he came. A big load of cum filled my butt for the first time. We kissed a bit more and then he walked away saying “i can’t believe it.” “I just can’t believe this!” At first i was like ” what is wrong with me!!! Worried i asked him he replied “nothing” “i kinda want more.” I said and he laughed “im too old i can’t no more. Im too old for you” For the first time ever i saw his ego go down and accepting the fact that he indeed was growing older now. His eyes seem tired he wasn’t the same man i first met some years back. We crossed the fence he said goodbye wanting to kiss me but i somehow turned my head avoiding him as he walked away looking back at me wanting to say something. He went back to the party and i sat inside my car. Tears filled my eyes. What had i just done!!!  Now this was not my first time having anal sex, i had done it with my boyfriend before but it was no fun since he always wears a condom because i don’t trust him, and he is also scared of cumming inside me even with a condom on. Wanting to forget what the cowboy had said about himself which hit me hard because to me he is  not old i stopped by McDonald’s bought a caramel sundae ate it and thought the cowboy is getting old does that mean we wont see each other again?! I was worried.

Did you have an orgasm? Did your partner(s)? yeah we both had.

What precautions did you take to prevent STIs and pregnancy? Did you discuss STI history? we do not. it is clear he cannot get me pregnant. And i trust him he trusts me.

What were your REASONS for having this hookup? We enjoy each other. He wanted anal sex and i wanted to give it to him. Make him happy

Were alcohol or drugs involved? If so, how much? He probably had a few beers. I did not.

What happened AFTER the hookup? How did you feel about it? What are your expectations/hopes for the future with this person? How do you feel about them now? Like i said i was worried. I loved sex with him he gives me pleasure and i give him too. I gave up hope. I had no expectations with him no more. The cowboy thing was over for me, no more awesome sex.

To whom did you talk about the hookup? How did they react? Nobody. to me it was over.

Was this a consensual and/or wanted experience for you? For your partner? i think we both wanted the experience.

Do you regret this hookup? If so, why? Not at all. Anal sex gives me lots of pleasure.

What was the BEST thing about this hookup? How about the WORST? Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Best thing: getting your butt filled up with cum with the person you enjoy sex with. Making his fantasy a reality. Worst: age difference for the first time.

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 or anything else? Later i found out this was his first time ever getting anal sex. Which at first i did not believe. He is around 17 years older meaning 17 years of getting more sex then me! So i went on asking another friend and he assured me that the cowboy had said the truth. Still doubting i asked him two days ago when i saw him looking right into my eyes he said” that was the only time i ever had anal sex.”

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