From what I could gather from Amanda's text messages, she must have watched my dildo masturbation videos dozens of times. I'd get stray messages from her about it at all hours of the day raving about those scenes. Others came in with a heart or the googly eye emoji, and on occasion, she'd ask me questions about that night and other previous experiences I had with sex toys. I'd answer each honestly, as she would answer me openly when I asked her questions.
What I never got was the birthday wish she had previously mentioned. I was expecting it, but it never came. In my mind, I kept thinking she was going to ask me if she could come to visit. To spend the weekend alone and naked. Or, ask me for a threesome with Jeff. Or maybe to sit and watch Jeff and I live and in person. And all of these requests would have been fine, but I didn't suspect she'd be able to get away and travel here without causing an immediate divorce. I pondered and pondered on what she was going to ask still in limbo on what she wanted. That is until one late night after I went to bed when she finally got the guts or was horny enough to ask. Her messages that night were lengthy and drawn out, but when she finally asked me, she wrote;
Hey, I know you have sent me a ton of fucking hot videos, but there's one thing I haven't seen yet. For my birthday wish, I want to see Jeff fucking you in the ass.
Followed by; if that's not too forward or embarrassing for you.
My initial thought was no. In my mind, I justified the no by thinking; I had sent her videos of me giving head, being squirted with cum, and fucking myself with a dildo. What else can I do for this woman? And I realize she was sending videos and pictures back of her in compromising positions with a host of elicit sexual toys. But, to have her see Jeff fucking me in the ass, for her entertainment, was a bit more than I was wanting to give. I didn't answer her texts right away regarding that, outside of "perhaps," as I wanted to think about it more.
It was embarrassing. It was compromising. Maybe less compromising or personal than me pleasuring myself with a dildo, as it would be making love with my boyfriend. As that's what gay couples do. Nonetheless, it is a bit more in-depth than just giving head. Moreover, even if she found a girlfriend and sent me videos of them both engaging in oral sex, it's not the same for her to be eating pussy, as opposed to having a cock rammed up my ass. I was a bit leery.
But I must admit, the more I thought about it, the more turned-on I got about it. More than anything was the exoticness of having him film it, while he was fucking me. As much as I get the pleasure of him being in me, I have never seen it. Whether riding him, or him being on top in the missionary position, I can envision it, but can never actually see it. Especially when it comes to being on my knees. I have no idea what's going on back there, outside of knowing it's in me. So, to see it would be really cool. It is a very bold request from her to watch him fuck me, but I could understand her curiosity. After some deep thought, I started to reconsider.
Moreover, and more enhancing was the fact that I must have watched the video I sent her of me riding my dildo, at least a dozen times myself. I got to see what that looked like and surely remembered the pleasure it gave me as it slid in and out of me. One particular night, I got so turned on by watching myself, that I got the dildo out, suctioned cupped it to the same book, and slid right on top of it. Sliding it back inside of me. I rode my dildo, watching the video of me riding it, looping the scene over and over again, just enjoying the pleasure of that night and this night combined.
Many nights while I pleasured myself anally, I thought of her. I wished she was with me helping me get off while my big long dildo was inside of me. Wishing she was there with a strap-on, making me suck it while I rode my dildo. Or even better, letting her ram her strap-on deep in my ass as I whimpered like a girl. Which is what I do every time Jeff fucks me. I wanted to slide my cock in her pussy, make her cum, then fuck her in the ass hearing her scream in pleasure, until I came deep inside of her. Things we had done many times before when we were together. But now would be enhanced sexually with the addition of a strap-on. All of these thoughts and ideas spewed from deep inside my conscious, just as the cum would spew from my cock when I fantasized about it.
All of these thoughts, ideas, and desires are erotic and liberating, even beyond sexual. And to review a video of Jeff fucking me, hearing his moans and groans, coupled with my whimpering as he did, was pulse-raising. And after fantasizing about it, and visualizing it, now I wanted it. I guarantee you I wanted it more than she wanted it. I wanted to see it. I wanted to hear it. I wanted to know what it was like watching his cock slide in and out of me. To see his point of view. To see how deep he thrusts it in. How his dick slides in and out. How it flexes and shifts. How long and slippery it looks wet with lube. So, I decided, even if I never sent it to her, I wanted to film that to see it for myself.
Jeff was coming that Friday night to spend the weekend. And I had no doubt we would have sex and I had no doubt, I was going to get my fantasy fulfilled. As Saturday night was drawing to a close, I started to get that giddy feeling deep inside of me. I wanted him. Not only for the video but as my man, my lover, and having him as my boyfriend. I still get very giddy when seeing his cock and watching him get hard. Kissing him, being seduced and of course sucking him off. I have also become very accustomed to having his cock inside of me. Even in my previous experiences with "men" (the trans girls), there wasn't a lot of anal sex for me, as I was always the man of the relationship. But now in this situation, I am more of the girl, so I am the one flat on my back, on my knees, or up on top of him riding his cock. And I really like it!
As we crawled into bed, I was wearing just a T-shirt and underwear, and he was only in his boxers as he usually is. We cuddled up against one another, just feeling the warmth and companionship of having someone next to you, which makes me pretty hot and ready for sex. I wanted his cock in me. I wanted to cum while riding him and I wanted to have him film this more than you could imagine.
As our warm touch turned to heavier petting and kissing, I was beyond ready. I love nights like this, when we are alone together, in the quiet of the bedroom. The seduction and passion that ignites lead to the romance which follows. I have always wanted that man, that boyfriend, that lover whom I was falling for. One I trusted and wanted sexually over and over again. And in this situation with him, I feel more comfortable, more feminine, and more willing to please him than in any other past gay experiences. I have loved us moving forwards and deeper with our sexuality. Which makes me want his love, his lust, his warmth, his body, and his cock even more.
As we kissed deeply, I got hard as a rock. My hand slid down between his legs and upwards, passing by his balls first, then onto his hard cock nestled inside his boxers, which was sticking up and pointing towards his stomach I slid my hand down into his boxers and started stroking his cock. I swear my mouth was drooling. I needed to be sucked, and my asshole was throbbing, waiting for him to penetrate me.
I slid below the covers, pulling his boxers down and away from his waist, and slid his hard cock into my mouth. I bobbed up and down on it, moaning myself as I sucked him off. I love giving head. Always have, but with him, it's more than just sucking dick. It's a pleasure I have come to love. It's a deeply satisfying, emotional fixation that I just can't get enough of. I'd suck his cock every day if he wanted me to. And him returning the favor the vast majority of times, or fucking me with it, just makes it even more desirable.
I slurped up and down on him for a good length of time. The feeling of his hard cock passing through my lips, across my tongue with the tip hitting the back of my throat, is a huge turn-on. I just can't seem to get enough of him and enough of his dick. I was beyond hard, beyond ready, and needed him inside of me.
I pulled his cock from my mouth and pulled his boxers down and off. I flipped the blankets off of us and leaned upwards and towards the night table. I pulled my T-shirt off, and my underwear down, as I flicked on the little night table light on and reached into the drawer. I pulled out the bottle of lube and a condom and readjusted myself down and in between his legs. I leaned downwards and started sucking him off again, while I held the bottle and package in my hands. I pulled his cock from my mouth and looked up at him from my kneeling position and whispered, "I want your cock in me."
Jeff smiled wide, as he knew, I was going to ride him hard. I opened the condom package with my teeth, holding the rubber between my lips, as I popped open the bottle of lune. I squirted a generous amount on my hand and grasped his shaft, slowly stroking him off and getting him all lubed up. I pulled the condom from my mouth and slid it over his hard cock, using the lubed hand to stroke the condom, getting it soaking wet and slippery.
I climbed right on top of him and grabbed his cock from behind me, positioning it at the right angle. I lowered myself down onto him and his big hard cock slid right into me. I gasped as his cock slid deep inside of me. My body tingled, my lust grew and my love of being fucked by him deepened more.
I rose and fell on his hard cock, just taking it all the way in and out, feeling the pleasure of being filled by him. I rode him for a while before I was concerned about recording this. I could see my phone sitting on the edge of the nightstand table. And I wanted to reach for it and just start recording, but I wanted his permission. I moaned out to him while riding him, "I wanna film your cock in me."
Jeff moaned out loud as if he was saying "yes" without saying the word. I lifted myself off of his cock leaned over and grabbed my phone. I hit record and slid myself right back down onto his cock, letting him slide right back up and into me. I rode hard and deep, thrusting my hips into his body, as my cock flapped up and down. The tip of my cock would smack the lower part of his stomach each time, giving me a thwapping sensation each time it hit, arousing me even more.
I reached behind me and tried holding the phone at the best angle to see his dick sliding in and out of my ass as I rode his cock. I let it film for a while, hoping I got a good angle and view. When I was done reaching behind me, I leaned back and put the phone down between our legs pointing at our dicks. I wanted to try and capture the angle he sees when I ride him. I wanted to capture his hard cock sliding in and out of me from the front side. Even though I was trying different angles, and hoped for the best, I wasn't about to stop and check my recordings. But in my mind, I was looking forward to seeing some great videos of him sliding in and out of me.
Jeff was moaning deeply as I rode his cock and I knew he wasn't too far away from cumming. I wanted him to be behind me, doggie style, as that is my second favorite position and if he filmed it, it would give me the best view.
"Baby, fuck me from behind." Spewed from my lips, as I bounced up and down on his dick.
