[MF] That time an older man introduced me to anal

First time posting a story, hope you like it…

Background: through complicated events I started a relationship with a man who was 50 when I was 18.

So we’d been seeing each other a few months and our relationship had been sexual from the very beginning.

One night we were playing with massage oils. He would rub some into me, I would do the same to him. A great way to relax. After a while I was on my belly with him rubbing oil into my back and my ass. Every now and then some of the oil would run down my ass crack and find its way down to my asshole and pussy. The oil trickling down to my butthole was kind of a nice feeling if a little ticklish.

We hadn’t played anally before which made him a little hesitant, but after a while I noticed he was rubbing more and more oil into my ass and deliberately spilling some more between my cheeks each time. Before long he started to massage that area too but I wasn’t expecting the finger he slid into my butt.

I drew breath and turned my head to look at him for reassurance.

“What are you doing?”

“I’m making sure there’s enough oil here”.

That could only mean one thing. I knew I could say no and he would stop…but I hadn’t tried this before and I liked him taking control. It was a difficult time in my life and being under his spell eased my mind about many things.

“I’m going to take your asshole, Sophie”. Words I will never forget. Nervous excitement and anticipation overtook me. I didn’t want to say no.

He removed his finger and oiled up his cock. It was a decent size but I would have bigger with later partners.

I lay my head on my pillow and spread my legs to indicate my submission to his request.

He pressed his cock between my cheeks but there was so much oil that it slipped around. Soon though he found my rear entrance and pressed his cock forward to enter my ass.

The oil and relaxation meant that it didn’t hurt like us been expecting. In fact this easy first entry I think led to me becoming the anal queen I am now. He pressed forward slowly while pressing his hands down on my shoulders, increasing my feeling of submission. I thought he might only enter me partway but that wasn’t his intention at all and soon he was deep in my insides.

I was even less prepared for what happened next. Beginning to thrust in my asshole, using one hand to steady himself, he then used his other hand to grab my ponytail and pull my head back. It told me absolutely who was in charge and I loved being controlled like that. I was his anal bitch without question.

Needless to say he was loving every moment and it wasn’t long before he announced, between panting breaths, that he was going to cum in my ass. It was the first time he had blown inside me as we’d only been having normal sex with condoms before that.

He came with his usual sexy noises and then with another surprise, proceeded to slap my ass a few times before pulling out. So turned on at this point, I begged him to keep doing that while I made myself cum with my fingers.

I’ve had more experiences since with both anal sex and older men, but that was the story of how I lost my anal virginity.

Comments and PMs welcome.
Sophie-Jane xx

Source: reddit.com/r/gonewildstories/comments/5iudtk/mf_that_time_an_older_man_introduced_me_to_anal

7 comments

  1. it’s a well written story.

    and before someone mentions that, considering it was your first time, it would have been more painful is more common than mousy people think that they are able to do anal easily. this is particularly true if enough lube is used, but are also highly aroused.

  2. I had a relationship with a 50 year old man when I was 16. I was his little girl, had me sit on his lap which got his cock hard. I tease him rubbing my bum back and forth. I then open his jeans, took his dick in my hands, made him cum to take the edge off. He was my first anal. He was gentle about it. He also introduced me to buttplugs.

Comments are closed.