I had met Josie at a bar and she had no qualms in letting me know that she was a shemale. We both were drunk and horny, so she let me feel her up. I had had gay encounters and considered myself bisexual, so I wasn’t afraid of touching another penis. It made me hard. I was too drunk for sex so I shared my contact information with her and when we met, there was a porn flick made on my camera while having sex with a shemale.
Josie had arrived at my apartment on Saturday and we were having a few drinks. I don’t know what got into me but I asked her if she would have sex with me on camera. She was quiet a moment and then she said, “Sure, why not.” She takes away my glass and pulls me closer, grabbing my cock. She massages and presses it, making me moan out loud.
I quickly make my way back with a camera in hand and set it up in front of the couch. I went over to her and unzipped my pants, showing my cock. She rubs the length looking at my face and then running a finger over the head. I turn a bit so the camera can record my cock and her hands as she rubs me. I would watch this again later for some personal pleasure time.
She presses my cock and puts her mouth on the head. Her tongue rolls over the sensitive spot and she sucks it. She starts blowing me, her head bobbing up and down. Her hands rotate on my cock as she sucks the top half. Her suction increases and “Ahhh!” I moan in pain. She stops and bats her eyelashes, then spreads her legs. She removes her panties and pops out her cock. She pulls her top down showing me her boobs and shaking them.
I had never really sucked a cock before and Josie had a huge cock. It was fat and thick, with a huge head. She touches herself watching me and I see the camera is recording every bit of sex with a shemale. She shakes her cock at me beckoning me to suck. I kneel down and hold her cock tightly. I want to measure its girth to see how fat it is. I squeeze her unintentionally and get a scream in response. “Sorry, sorry,” I mutter and in order to pacify her I bend down sucking her cockhead. She tastes musky, I guess most cocks taste and smell like this. I suck on the head and try to do what she was doing to me.
I rub the length of her cock and keep sucking on the head. Then she thrusts her hips and the cock goes further into my mouth. I gag but then breathe through my nose and I am ok. I try to deep throat her but there is only so much I can take in. I suck and suck till my mouth hurts. She presses her own balls and massages them for pleasure. I press her breasts and squeeze them hard again. They are hard and I keep pressing till she thrusts her cock again deeper in my mouth.
I gag again and stop, a little pissed. So I slap her boobies once to show my displeasure. She shrieks and laughs. She lays on the couch and spreads her legs. “Now what?” she asks. “Now, I fuck you,” I respond. I bring a bottle of lubricant and a condom packet. As I cover two fingers in lube, she starts to touch and massage her cock. I first rub her entrance with the wet liquid and then try to push in. Her asshole resists and I pull back my hand.
“One finger first,” she tells me and I nod. I take some more lube, pouring it into her ass and gently push one finger into her asshole. It goes in slowly and I feel her tight ass around my finger. I pull back and add a second finger. It is tighter, but with lube it is possible. I finger fuck her ass as she plays with her fat cock. I keep moving in and out of her ass as my cock waits to get in. I add a third finger and although it’s tight and I hear her moans, I continue. I keep rubbing her hole and finally, I feel her channel relax a bit.
I cover my cock in a condom, add more lube and push my cock inside her asshole. I go in without much resistance. I wait a bit so that she gets used to my cock inside her ass. Then I start moving in and out of her asshole. Her large balls caress my cock with each movement and I feel good. I hold her cock at the base, like really hold on to it tightly and increase my pace. I want to get my orgasm while enjoying sex with a shemale.
I start moving faster and feel her channel contract around me. Her ass is massaging my cock and I feel ready. I press her, massage her cock with both hands as I move in her ass. Then I see her boobs bouncing and grab those with one hand. I want to squeeze and squish them, so I do that. They are firm and not soft but it will do. I press them hard and feel my orgasm move through me. Josie is masturbating and watching me and then her cum falls on her belly.
I cum hard in her asshole, shaking. I fall on top of her and try to calm down. This orgasm was thrilling and I take a good, long time to relax. Josie leaves after that and I switch the camera off. Now I have something naughty to help myself too on lonely nights. Josie gave me excellent visuals to masturbate to especially sex with a shemale who was too hot.