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Ok so a couple days ago a made a post talking about how my boyfriend and I started to explore cuckold stuff and how we went to a party and I meet a really cool guy named Tommy and he ended up fingering me in the hottub. I texted him the next day and we ended up setting up a date for last night. Here’s how it went.
We talked about the boyfriend thing pretty early on, we were talking about our past relationships and I told him that im actually in a relationship currently but my boyfriend is okay with and actually encourages that i go out on dates with other guys. Tommy was pretty shocked at first and didn’t know how to handle it but was ultimately ok with it. He ended up asking me out to a comedy club that has food and pretty good drinks. I wore a blue tank top (cause I know it gets hot inside) and a puffer jacket over it with some tighter jeans to show off my ass a little.
The food was alright but the conversation was great, he was a really funny and nice guy. He was even willing to help me take a picture of and my meal after i told him it was a thing i like to do. We kept buying drinks ( he was buying) and I was a little loosened up after starting the date nervous. Eventually the comedy started so the conversation was slower while they were on stage. At one point the comedian was doing crowd work and pointed to our table to ask how we were doing. He asked if we were on a date to which I said yes, then he asked if we were planning to fuck tonight. Tommy got red with embarrassment but I said yes. The comedian laughed and moved on but tommy asked me ” Actually?” I said yeah why not. And he said ” Why waste any time then. My place?”
He ordered an Uber and it was a 15 minute ride to his apartment. While we were waiting I texted my boyfriend that i was going back to tommys place and he said it was great. He just asked for pictures. Me and tommy were trying to be considerate of the driver but we’re still touching each other alot. We kissed a little bit and I had my hand in his lap teasing his hardening cock. When we got to his place ( which by the way was very nice) we turned up the make out immediately and had our hands all over each other. I went from teasing to full on giving him a hand job through his pants, he was moving between groping my ass and tits. We stumbled our way through the apartment like this. Then, right at the stairs he picked me up and carried me up them. It was so hot with his arms around my waist as my tongue was still in his mouth. When we got to his bed he gently set me down and his hands went from groping to starting to remove my clothes.
I kicked my jeans and panties off as he pulled his shirt and pants off then he turned to me and took my shirt off. When he undid my bra exposing my breasts he moved his kisses from my lips to my nipples. it was so hot, I was moaning his name as he played with my boobs and rolled his tounge around my nipple. His perfectly light biting mixed with licking showed just how much experience he really has.
Eventually he worked his kisses down my body and started kissing around my vagina. The combination of his tounge in me while his fingers worked my clit was heavenly. I was so engrossed that I was barely able to ask tommy if it was OK that I took pictures. He said it was fine, some cute line about ” Glad im good enough that you want to remember me”. I sent the picture to my boyfriend and said ” dates going well lol”. I told him I was getting close and he pulled his head up and went back to kissing me while he stuck his fingers in and went at it hard looking for a climax. The taste of his spit mixed with my pussy that was coming out of his mouth as we made out was weirdly sexy. I came hard. All over his hand and bedsheet while half screaming half moaning into his neck.
He pulled back and asked me if I need time or something. I barely heard him because I started crawling towards him. My prey was the huge tent he was pitching in his underwear. I had felt him up and knew he was probably above average, 6.5 inches maybe, but when I pulled down his boxers it looked perfect. His now rock hard cock sprung out and nearly smacked me in the face. I giggled a little bit and grabbed it with one hand lifting it up and sniffing at his balls (I’ll admit that I love the musky smell ok, sue me). I planted a few kisses as I worked my way back up his shaft. I handed him my phone and said ” I usually make my dates take a picture of me and my meal” he laughed and quick took the picture but I noticed he held onto the phone.
I took the tip into my mouth, swirling my tounge around his cut head. Then started to work deeper and deeper, it was surprisingly girthy and I had a little trouble pushing my way through. Eventually my saliva had lubed his whole dick and made taking the whole thing a little easier. I started to pick up pace. Mouth full of dick. Using one hand to stabilize myself on his body and the other to play with his balls. I would roll them between my fingers and time it so that I squeezed a little bit when I went particularly deep and try to force myself to make eye contact with him despite the gagging. One time I looked up at him and noticed he was filming me, I took his cock out for a second to say a playful ” heyyyy” but when he only responded with ” keep going baby” I got right back to work.
When I could feel him get close I teased him right up the edge then pulled him out and gave a him just a small kiss on the tip. A string of spit ran from his cock to my mouth that I twirled with my finger and licked clean. ” I cant let you cum just yet. You promised to fuck me.” He protested slightly at being denied but was excited about getting to the main course. He walked around the bed and pulled a condom out of his night stand and slid it on. I worked it down his shaft a little bit pretending I needed to check it. Then laid down and asked ” How do you want me daddy”
” Ass up baby” then he added ” Please”. I chuckled and turned around sticking my ass in the air and wiggling a bit teasingly while grabbing a pillow. ” Please” i emphasized ” fuck me now”. He lined his dick up with my ass, slapping my ass softly with it before lining it up at my entrance. ” Tell me if you need it slower baby” he said as he first pushed in. My pussy clamped down on him and we simultaneously let out a moan. He continued to slowly work into me. in and out every time going slightly deeper until he was about 3/4 into me when he moaned out ” fasterrr”. He quickly picked up the pace and by the time he was all the way he was full on pounding me. My ass would slap against his pelvis with each thrust and his dick would make a wet squelch as he pulled back the noises mixing with his soft grunts and my loud moans to create an intoxicating scene. He was ramming his dick into me and stretching me out again and again for a solid 4 minutes when my legs gave out as I came. I screamed into the pillow with pleasure as a wave of heat radiated from my core.
He paused for a moment. ” Ohhh fuckk. Keep going” I moaned out. He went right back to it. Fucking me hard as I lay down flat face in the pillow. I was kind of out of honesty. Couldn’t tell you how long he fucked me or how it went as rolling waves of pleasure overlapped and linked together to Keep me in a state of orgasmic bliss. I remember him telling me he was close. He pulled out, my pussy immediately aching and feeling empty. He pulled off his condom and I felt rope after rope of his hot cum paint my back.
He collapsed next to me and we layed there for a while. He eventually turned my head towards him and gave me a kiss asking if I was OK. I assured him I was and just needed a moment. We layed in bed for a while. eventually getting up to take a hot shower and wash myself clean, take my makeup off and get ready for bed. ” Hey im gonna stay the night”
” ok” he responded from the kitchen.
I grabbed one of his shirts, still bottomless and followed his voice. He had made us a frozen pizza that we shared before we went to bed cuddling each other. I had completely forgotten about my boyfriend for the end of the night but woke up to about 4 missed calls and tons of texts. I called him quick to explain everything and he said he was glad I had such a great time and was actually happy that I was so into it that I had forgotten about him. He asked if I had any more pics and I went to send him the bj video that I knew tommy had taken. When I checked I saw multiple videos of me getting railed and one of me getting backshots. I sent them all to him and told him id be home soon. ( Before you ask, no I won’t be posting them or sending any pictures of me in dms)Tommy made me toast for breakfast and bought me a Uber home.
It was an amazing night that we have plans to repeat again soonish. Im glad I got to share this story and journey on reddit. There’s more stories( past and hopefully present) to come. Thanks XOXO
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