Hot gay stores how i became a sissy slut

I was 20 years old and had been going out with my girlfriend for about 9 months. Everyone thought I was straight, and although I had never really acted on it, I had often had gay thoughts and wanked over other men. So when my girlfriend told me that she wanted to fuck my arse with a strap on, I was interested.

I was at university at the time but was home for the holidays. I only come home during the holidays, so at first both me and my girlfriend were super horny for each other. She therefore thought it would be a good idea that we try something new. I was stunned. Just try it for me, please.

She wanted it, and I desperately wanted it. So eventually she persuaded me to try it. She said she would buy all the equipment and we would try it the next day. The next day she came over to mine as usual after work, and greeted me with a big smile as I opened the door. We went upstairs to my room and as she showed me all the equipment I immediately became hard, while trying to hide it and act unsure.

We started with the normal foreplay, kissing and undressing eachother.

Sissy Confessions

I did as I was told, slightly turned on by being told what to do. I felt her stroke up and down my legs, before spreading my cheeks and squirting lube onto by anus. As she did so she slowly massaged my anus with a finger, before slipping it in gently.

At first my anus resisted, but there was enough lube that it slipped in easily enough. She started to finger me rhythmically before slipping a second finger in and upping the pace. The feeling was amazing. I started to arch my back a bit, pushing myself onto her fingers and silently begging for me.

I was fully erect, and pre-cum was dripping onto my bed below me. After a few minutes she stopped, and without saying anything put on the strap on and started to lube it up. I tried to turn around to look, but she grabbed my head and pushed it down into the bed.

She rubbed the dildo up and down my crack, teasing me with the thought of it, before slowly pushing against my anus. It slipped in fairly easily because of the lube, but once inside it made me gasp in pain. She was right, because after about 10 seconds the pain went away and I relaxed.

Slowly she trusted into me. She kept going until she bottomed out, touching my prostate as she did. My dick jumped a little bit and I let out a little moan by accident. Taking that as encouragement, she started to fuck me faster. I had never felt anything like it.

I remember thinking that I wanted her to fuck me for hours, and I lost myself in the pleasure. Taken aback by the tone I was quick to respond, moving onto my back and lifting my legs into the air, revealing my arse to her. She quickly inserted back inside me as I let out a gasp of pleasure.