[MF] My first time being pegged. I paid someone to do it.

I am normally a pretty dominant person in bed. However, I have always had this aching desire to be submissive and be on the “receiving” end. Pegging has always interested me as the act of being penetrated is so foreign to me.

A few weeks ago I was browsing reddit F4M post for those interested in pegging and found a few posted by someone in my area. They were several days old so I had very little hope that I would get a response. But lucky for me she responded that she was still in the area on was interested!

Now this part I’m not that proud of. I paid her. Not something I was intending on doing but my desire to be fucked was high and I was feeling generous. Plus she’s got to make a living.

Once we agreed on a price and a date I bought a strap on (didn’t want a used one being used on me). I also figured, if this is going to be the only time this happens I’m going to go all out. So, I also bought a chastity device and some panties. If we were going to do this I wanted to do it right.

Finally, the day came that we were going to meet up. She had given me some prep tips and I had some familiarity from fucking myself with dildos before. I thoroughly cleaned out for her. I hadn’t told her about the panties or cock cage and wanted it to be a surprise. So, I put those on while I was at home. The cock cage was surprisingly hard to get on. Mostly because I was so excited that I kept getting an erection while placing it. Eventually I got it on and put on this pink lacey thong as well. I could not believe how good and slutty it felt. I felt so fucking feminine. It was so new and different, I loved it.

We initially met outside her hotel room. We hadn’t exchanged pictures before hand so I was very nervous about meeting and very ready to abort if I felt anything was off. Luckily she was very warm, welcoming, and normal.

She was much shorter than me and very skinny. She had a almond skin tone, black curly hair and multiple piercings. We entered her hotel room and I put the bag I was carrying, that contained the strap on and keys to my chastity, down on the couch.

We made small talk for a few minutes and she apologized for the mess. She was wearing a see through white t-shirt that revealed puffy dark nipples and had on some small booty shorts. I said “how do we start” and she took off her shirt to reveal some small perky boobs and comfortably said “well why don’t we get undressed”.

I complied and removed my shirt and started to unbutton my jeans. To be honest I forgot I had a cock cage and panties on for a second. She was surprised. She smiled and giggled, “I love it!” reaching out and flicking my cock cage with her fingers. “Really?” I asked. “I thought I might freak you out”. “Of course not!” she said.

I got out the clear strap on dildo I had bought. It was thick and measured 7 inches. She expressed surprise that I would want to start with something so large. But I admitted that I had often played with my ass in the past and I had actually tested this one out.

She put on the strap on and asked for some help. I got down on my knees in front of her and helped tighten the straps. Once fully on she grabbed the base of the dildo and started waving it in my face. “Is this the big cock that you wanted” she asked. “Absolutely” I said. I grabbed the dildo from her and licked from the base to the tip. “Want do you want me to call you?” I asked. “Daddy” she said confidently.

“Yes daddy” I responded and the wrapped my lips around the dildo. I started bobbing ym head up and down on the plastic cock feeling it fill my mouth. I felt her hands warp around my head and her hips start to thrust and she began fucking my mouth.

I cannot express how good this felt. I had never been in this position. I had never felt this submissive and vulnerable before. For someone used to being in charge and dominant this was very weird, good weird.

Eventually she picked up the pace and force. I tried taking the dildo as deep in my throat as possible but couldn’t really get that far. I often gagged, having to pull off. But I would lick my spit of her cock and continue sucking like a good slut.

She had already laid out towels and instructed me to lay down on them. I willing complied. She gabbed some lube and put on some gloves and lubbed up a finger. She moved in-between my legs and reached down. I felt a cold finger beginning to play with my ass and moaned. She slowly pushed into my anus and I moaned “Yes daddy!”. I felt her being to warm up and stretch my asshole. Her other had grabbed on to my balls while she did so. Eventually she pushed deeper and hit my prostate yielding a very loud moan from me. I had played with my ass plenty of times before but there is something different about having someone else do it.

After warming me up and ensuring I had cleaned well for her she positioned her strap on in between my legs. I felt the head of it being to push in to me and pop into me. My hole felt so stretch and she stared deeply almost completely through me while she pushed her cock deeper into me. I could not believe I was finally getting fucked.

She slowly started to thrust in and out of me and the pressure felt amazing. I closed my eyes and just laid back enjoying her movement. She leaned in closer to me forcing the strap on deeper into me. I reached up and cupped her small breast which felt so good in my hands.

After I was clearly warmed up by the cock she started thrusting faster and faster. She moved my hips up so that she could fuck me deeper. I looked down to see my caged cock struggling against the restraint and bouncing with each thrust.

She told me she wanted to play with my cock while she fucked me and asked for the key. I reached over and gave it to her. It felt so good have a full erection after being in the cage. She started to fuck me again but this time slowly stroking my cock.

“Your such a slut” she told me as she gabbed my entire cock and balls. “You like your little boy pussy being fucked don’t you”. I honestly can’t remember how I responded because I was so lost in being fucked.

I don’t know how long we did this for but she eventually pulled out and told me to turn over. This is the part I was waiting for. I so badly fantasized about completely giving up control and bending over for someone that I nearly came just getting in position.

I put my ass up in the air and my face down. Unfortunately she was just a bit to short for that to work. So I raised my head but made sure to arch my back in the most feminine way possible. Her hands made their way to my ass and her strap on cock yet again pressed into me. This time there was no warm up. She immediately started fucking me as hard as she could. Each thrust felt amazing. Not only was the sensation of my asshole being stretch good, I could feel each thrust travel through my prostate and up into my cock. It was like she was fucking my cock from the inside.

After several minutes of moaning and calling her daddy I had to cum. I asked her permission and she said yes. I reached down to my rock hard cock and began stroking. Within a few second I started spraying cum all over the towels. With each thrust more and more cum leaked out of my cock.

I collapsed out of breath next to the towels. She laughed and bent down next to me picking up some of my own cum with her finger. She told me to turn over and I did, eyes still closed. I felt a finger start to circle my mouth and without thinking opened it. I was met by the taste of my own cum and began instinctively sucking on her finger. “Thank you daddy” is all I could manage to get out.

Source: reddit.com/r/gonewildstories/comments/onuxgs/mf_my_first_time_being_pegged_i_paid_someone_to