What’s your gender? Man
How old are you? 37
What’s your race/ethnicity? White / Caucasian
What country and/or city do you live in? Victoria
Highest education received: College degree (eg., BA, BS)
What’s your occupation? Self employed
What’s your current relationship status? Engaged/Married (monogamous)
Religious affiliation: Christian
How religious are you? Not at all
What’s your sexual orientation? Mostly heterosexual
How many sexual partners have you had in your life (including oral sex)? 37
How many hookup stories have you here posted before? 2

She fisted me

How long ago did this hookup happen? 4

What was your relationship status at the time? In a relationship (monogamous)

How would you best classify this hookup? Friends-with-benefits

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? Gem I’ll call her was an older short round woman I met from a sex site. She wanted a younger man to come and fuck her in all holes and was curious to me being bi-curious

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? We had been texting each other during the day and talking about everything we have done and wanted to do sexually. I had told her about liking and play done on me and wanting another MMF one day and she wanted to help me with that as she did know a few bi guys and might be able to do it one day. She asked me over that night and to pack some of my anal toys for her to use

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 got to Gems house and was created by her in just a towel and still wet from her shower and she lead me straight to the bed room. She know what she wanted and wasn’t wasting any time I getting me undress. We kissed and I removed her towel so I front of me was a 5 foot nothing round lady that had just turned 50 and me 35 6 foot fairly athletic two totally different builds but after the same thing.
Gem pulled me onto the bed as we kissed and it didn’t take her long to find my hard cock and start wanking me. My hands found her shaved pussy and a couple fingers slipped straight in as I kissed and played with we tits. Gem pushed me onto my back and climbed into the 69 position and tried to deep throat my 8 inch cock without any luck. (Only and inch and a half and she was there closest anyone had come before).
Her pussy was sweet and wet and soon my face was covered with her moisture. While giving me head I felt her spit on my but and rub her fingers on my ass teasing me and slowly opening me up to take a couple of her finger. After a while she got up and licked her pussy juices from my face and kissed me.
She it me to kneel face down with my ass in the air as she got behind me and rimmed my ass something no one had done before. I could feel her push her tongue into my asshole and flick it around as she pulled my cock. Gem then grabbed the bag of goodies that I had brought along and lined my ass up with plenty of lube and pushed some into me with a couple of finger. She of a 10 inch dildo not to thick and started fucking with it pushing it all the way way in. This whole time talking to me about how hot this was and that she has always wanted to fuck a guys ass. Asking me if what she was doing was ok and how best to do it. After a while she left that dislocated in my ass and she another that was about the same girth but only 7 inches and started to work it in along side the one already in my in my ass.
I had never taken two dildos at once but Gem had managed to get both in me and it felt amazing and didn’t hurt at all. Gem left both these dildos in me and got off the bed saying she will be back very soon.
I stayed there two dildos up my ass as she left the room and returned a few minutes later sitting on the bed next to my head and showing me this monster vib that was at least 12 inches and as thick as my wrist saying she wanted to fuck me with it. I found her pussy and fingered her with two fingers as we talked about that did Lo and how she hardly ever uses it as it’s was too big for her and the time it takes for her to work up to taking it. While we were talking I had managed to get four of my Ingres inside her with my thumb starting to push in. I told her I find that hard to believe as I almost have my hand in you. Gem was shocked when she looked down to see most of my hand in her. I took the vib from her and revived my hand and pushed the head of the vib into her still open pussy till she had at least 8 inches inside her. What a sight me ass in the air with two dildos I. My ass and gem with a monster vib in her pussy. I fucked her for a bit with the vib before turning it on slow vibrations to start with working it up to full speed. I moved so I could suck on her clit as I ducked her with the vib. This didn’t last long till she exploded with a gush sliver my face. I turned the vib off and pulled it from her leaving her pussy gaping.
Gem grabbed the vib and moved back behind me and fucked my ass a bit more with the two dildos in my ass before she pulled both out and replaced them with the monster vib. She slowly worked it deeper into me getting to its thickes point and about 10 inches deep. Gem turned on the vibrations and fucked me for the next 5 minutes while she lay beneath me sucking the head of my cock. I told her that I was going to cum and she kept going till I cum in her mouth and she pulled the vib from my ass. I rolled onto my back to get my breath back and gem kissed me and shared my cum with me which I always enjoy.
As we lay there talking she asked me if anyone had ever fisted me which my reply was no. She told me she wanted to try if I was keen and she wanted me to try and fist her in return.
I stayed laying on my back as Gem lubed her hand and my ass again. She worked four fingers in very quick after that big vib. I was feeling very full at this point as gem moved her hand to try and get her thumb inside as well. After a while she had all five fingers in me up to the widest part of her hand which I felt was about my limit. Gem slowly fucked me like that for a while and couldn’t get past her knuckles. She left her hand in me thinking that this was as far as we were going to get and gave me a kiss and asked me if I had had enough. I told her to keep her hand there and fuck me with it till I cum again. I started meeting her thrust as she fingered my ass with her five fingers. It was so enjoyable and I must of relaxed and all of a sudden Gem yelled out that her hand was all the way in. She grabbed my phone and took a bunch of pics.
While she was taking pics I had turned her so I could play with her pussy. Me on my back and Gem on her hands and knees ass and pussy facing me. I started fingering her pussy which had gotten even wetter. It wasn’t long and I had gotten to the point all my fingers were inside up to the knuckles and couldn’t get any deeper. I told Gem where I was up to and took some pics for her. She was looking at the pics I took of my hand inside her and she started rocking fucking herself on my hand. Working minutes I was all the way inside her. Wow both of us fisting each other. We both moved our fisting hand in time and within minutes I was cumming again in her mouth and moments later Gem cum hard on my hand again having a squirting orgasm one of the biggest I’ve seen.
Slowly I pulled my hand from Gem and she did the same to me. We had a bit of a breather and talked about what had just happened. She the said She wanted me to fuck her ass and dp her with a dildo in her pussy. I want going to pass this up as Gem got on her hand and knees. I got the monster vib again and had it ready. I lube her ass which didn’t need much as her ass was covered with her own cum. I pitched the head of my cock into her tight ass and waited for her to get use to it for a bit. Then I slowly fucked her getting deeper all the time. When I was almost fully inside gem. I paused and grabbed the vib. Slowly I pushed it into her pussy feeling it fill her and making her ass even tighter. Gem reached back and said she will take control of the vib so I can focus on fucking her ass. As I started fucking her ass again she started fucking her pussy with the vib. Asking me to fuck her harder and faster it wasn’t long and I was ball deep in her ass fucking fast. She had turned the vib on flat out and withing minutes both of us were cumming again this time deep in her ass.

How sexually satisfying was this hookup? Very

Did you have an orgasm? Yes, more than one

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? We did catch up a few more times over the next few months which some of them is for another time. We pushed our limits which was good and it was a great place to do so as we both had a great understanding of each other. Pity we won’t closer in age think it could of even been better

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting, Emotional intimacy, closeness, connection, Hoping or expecting it would lead to something more, Power / Dominance, Submission / Relinquishing power, Making new friends, It was easy / convenient

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? a couple of other that did join us later

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

Do you regret this hookup? Not at all

What was the BEST thing about this hookup? The ability to explore without judgement

What was the WORST thing about this hookup? Age difference

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? I love another friendship like this one again

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

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

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