14 May 2020

I have written about Trish before (part 2 is missing - for some reason deleted), so for some background, check out “Trish pt 1”

This beautiful, extremely sensual and sexual, classy woman, 15 years my senior, had a very exiting time for about 18 months about 20 years ago. I haven’t seen her since we parted ways but I do think of her often and wonder what she is doing now. My memories of the times we spent and the adventures we had are crystal clear and always make me very hard as I recount them.

One Saturday afternoon, we were in bed, after some serious fucking in a number of positions. I had just fucked her doggie style, a favourite of us both and had pumped what seems like gallons of cum into her pussy. As we lay recovering, we began to discuss our fantasies. Trish asked me what we hadn’t done that I would like to. I told her, perhaps rather too quickly that I’d like to watch her with another partner. She replied that she was open to the idea (wow!) but we would need to think and discuss further and it would take some arranging.

In reply to my fantasy, she calmly and quite unexpectedly informed me that she would like to try anal (double wow!!)

To say I was surprised was an understatement; anal sex had never been mentioned before. She went on to tell me that previous lovers had asked her but I was the one she wanted to try it with. She had been thinking about it a lot and was ready to try it. My cock began to stir at the thought, even though I’d cum twice in the last 2 hours. This was a very unexpected turn on.

Trish continued that there were only 2 conditions: hygiene was very important, so if we did have anal sex, no other sex afterwards, until we’d both showered and a condom was essential. No problem there.

Trish added that her fantasy had the advantage that it took no preparation or planing at all - we could do it now, or anytime we wanted. (Triple wow!!!)

We began to kiss, running our tongues around each other’s and beginning to caress each other’s bodies again. I played with her nipples; squeezing, gently biting and pulling them with my teeth, then licking them and blowing cold air over them. Trish had her eyes closed and her head back, her hand rubbing my hardening cock.

I reached down and slid my fingers into her very wet and cummy pussy, moving my finger around between her legs and rubbing my finger over a place I had never entered before. My cum, from her pussy, allowed my finger to slide inside her butt. Trish gasped and moved her hand down to hold my wrist, controlling how I fingered her butt.

As she began to relax, I rolled her onto her side and moved into a position, facing away from me, with her butt pressing against me. I lifter her leg and slid my, by now, extremely hard cock up and down her cum leaking pussy, then inside and began gently fucking her pussy. As we never used condoms, neither of us thought to put one on and my thrusting got harder as the pleasure consumed us.

Whilst my cock was sliding in and out of her pussy, getting covered in my previously deposited load, I slid my thumb into her slippery bum hole. I squeezed some lube around and into her butt, before I pulled my cock out of her pussy and on the next stroke, pushed it into her arse.

Trish and I both gasped. I had only just entered her arse and I held my cock still. Trish’s face was a picture of ecstasy; eyes closed, head back, lips slightly parted. I felt something moving near my cock and as I reached down I felt Trish’s fingers rubbing her clit. I slid my cock further into her arse, slowly, until I was balls deep. The feeling was electric; my cock in her tight arse and her fingers in her pussy. I could feel her fingers massaging my Cock through the flesh wall And Trish whispering, “ fuck me.”

I began to fuck her arse and as I did so, moved my hand around so that my fingers could join Trish’s in her pussy. As her arse relaxed, I fucked her harder and faster; the tightness of her arse gripping my cock and the feel of our fingers in her pussy causing previously unknown pleasure.

This was such an amazing feeling and I knew I wouldn’t last long, Even though I’d previously cum twice. I told Trish I was going to cum soon and she responded by pushing her butt into me, matching my rhythm. I could feel my orgasm rising up and I could feel my cock beginning to swell.

Before I could cum, Trish let out a groan and tensed up; her arse gripping my cock (that’s what it felt like anyway, it may have been the pressure of my cock swelling in her arse) and we both came together. My cum pumping into her arse and her pussy squirting over our hands.

Some time later, after we had come down from this high, we both agreed that anal sex was awesome but we would only do it on a special occasion (that rule went out the window too), with Trish wanting it quite often - not every time but more than special occasions.

What we’re the series of firsts?

First time anal with Trish


The first time I experienced a woman squirting.

Thanks for reading; let me know if you want more stories about Trish, or the bosses wife from a previous story.