My First Pegging Experience

I have always had a yearning fantasy to see how it wonderful it is to be on the receiving end of a good pounding/fucking...from a woman. That's right, a feminine figure with a luscious bod, but has the mind curious and open enough to fuck a man's ass... With a strapon dildo. And to all the ignorant cunts is not gay to receive pleasure from a woman even if it's anal related. So pegging has always been a fav of mine since seeing a scene from a movie (Deadpool for all you curious fucks out there 😈🤣) and ever since it's been a go to for me in porn alongside femdom.

I've searched on social media to find like minded women, and I have but due to my restrictive situation, the opportunity just vroops past me at the speed of light; that was until one day what should've been the best day of my life came. I joined an adult WhatsApp group from Facebook to quell my boredom and I met a milf that was surprisingly into it. So we texted and texted until we decided to meet one day. I had a seminar to attend that day and it was to be finished at 1 in the afternoon so after that my day would be free. My father wouldn't expect me until the latest 6 o' clock in the evening so I planned the day before. Shes from Kingston and I'm in St Ann so I arranged payment for travel for her to come to ocho rios. When we met in the town, we took a taxi to a Gurst House/Motel in a residential neighbourhood.

We arrived at the place, paid the worker for a room. We talked for a while and prepared ourselves for the fun until we got things started. I came out of my wheelchair and sat on the bed and took off my clothes while she went to the bathroom and did the same. I had bought a strapon and some from lube from Amazon a while back so I took it out for her to put on. When she came out she was wrapped in a towel with nothing underneath, I then said "why yuh have that on? Yah go fuck me Inna it??" and with that said I withdrew the towel from her body and discovered her hidden treasures.

She had the most supple breasts and thick thighs. Her thighs were so thick they hid her raw meat shut. She turnt around and displayed her ass to me.... I'm a breast guy, but a nice ass on a girl may turn me in a battyman too! (No pun intended 🙂) I fixed the straps of the strapon for her to put on and one couldn't even wrap around her leg properly..... But it held. She then laid on the bed and I went in to kiss her lips, her neck, her chests and her breasts. She then told me something that drew the complete bitch out of me: "Suck off me hood" she commanded me. I felt goosebumps all over me and my nipples and pea sized cock got hard. I applied a dab of the lube I bought (it was flavoured) to the dildo and started sucking.

She held my head down and played with my nipples and I sucked and deepthroated all 8.6 inches of that shit like a good bitch, to where I knew if she was a tranny with a dick I'd make her cum period. She then got up and I knew it was my other hole's turn to lose its virginity. I assumed the position while she prepared to stretch me out. She applied more of the lube onto her hands and penetrated my now devirginized ass . I let out an audible moan to let her know that it felt good as her fingers kept roaming about in my ass. She took it out and then replaced it with something evidently bigger, the dildo. She inserted it slowly and gave me some long deep strokes. I started moaning more. Now I know how it feels to have a big dick stretch a tight pussy.... Except in this case it wasn't a pussy being stretched 😌. She placed her hands on my lil ass dick stroking it... Like it does anything for me other than get stiff from the thought of being anally probed.... I placed her hands on my chest where she started to play with my nipples again... Now that gets me off... "A dat you love eeh bitch" she whispered while now going deeper inside me. I replied "Yes mummy, pinch mi nipple and fuck out mi hole." We continued for about 2 mins more until she got a phone call. She stopped and slowly took her dick out my ass which felt so good coming out. She answered the call and spoke on the phone for a couple secs then came off saying she has to go because of a prior engagement that has to be met before she goes back to kgn... I looked at the t.v to see it was a couple mins to five so we cleaned up and put back on our clothes and got ready then I called the taxi after. We said our goodbyes at the drop off point then I went home. Although her appearance and lifestyle wouldn't be approved by my strict parents I thought of having a relationship with her but after a while I lost interest in her because all I was to her was a Gold Mind. As her Golddigger side came up very strong, so I eventually deleted her number and moved on with my life.