The time I [M] 28 finally closed the deal with a MILF [F] 44 I met on OkCupid

A recent LinkedIn notification inspired me to share this experience. Recently I’ve been looking for a new job, and while I was scrolling my feed, I saw a familiar face posting about her new business. For this story, I will refer to her as Sharon. As soon as I saw her profile picture which showcases her beautiful green eyes, my cock began to thicken in my pants and I’ll tell you why.

While working in Savannah, my job often had me traveling to Charlotte, NC. Whenever I went to new cities, I would peruse OkCupid and Tinder to look for some locals to go out with. Truth be told I wasn’t having much success with Tinder, so I decided to focus on OkCupid. My age preferences were set to my age at the time (28) through 55. I am an equal opportunity lover, but truth be told it was mostly due to my MILF fetish. After about a week in Charlotte, I returned home to Savannah with no luck. After work one day I checked my OkCupid profile and noticed I had a match with a beautiful 44-year-old woman, Sharon.

I remembered her from initially liking her profile, but after the match of course I had to take a closer look. Sharon was 44, had an athletic build, and she seemed to have a cool almost hippie style (one of her photos was her in sundress with paisley print, visible GD tattoos, and her profile had some quotes basically referencing free love and smoking weed). She had bright blonde hair that was about shoulder length, and a beautiful smile that was complimented by a pair of stunning green eyes. From what I could tell from the photos, she didn’t have the biggest breasts, but had a fantastically shaped ass.

Sharon actually sent the first message inquiring what I was up to that weekend. I explained my situation with travel for work and how I was not in Charlotte currently. After messaging in the app and getting to know each other a little better, we exchanged numbers. I didn’t have her number for more than five minutes before I got a flirty text from Sharon saying how it was too bad I wouldn’t be in town. I decided to play it smooth, and asked her what would happen if I was in town. Sharon then sent me a selfie laying on her front in bed (fully clothed) with a nice angle showing her arched ass with the text “I guess you will never know.” At this point, I couldn’t wait to get back to Charlotte.

Fast forward about a month, and Sharon and I had been texting regularly. The conversation had gotten more sexual, and we had even started to exchange some partial nudes. For me, there is nothing more hot than when a woman gets turned on by my dick. I had shared quite a few photos showcasing my package. You know the classics: throbbing boner outlined in my basketball shorts, standing up flexing with my hard cock hanging out at 90° angle, laying down in bed getting the angle just right to make my dick look a little bigger lol. Sharon absolutely adored them, and would tell me how she loved to pleasure herself while looking at my photos and imagining the real thing.

The photos she would reciprocate with only got me more eager to travel to Charlotte. Sharon was even sexier than I initially thought. You could tell she regularly worked out because her body was very slim, and she had great muscle tone with beautifully tanned skin. Her tits were way bigger than I initially thought, for they looked to be about C cups and were perfectly proportionate for her body. Her nipples were a dark pink color that were certainly bigger than average,and I absolutely loved them. Her ass was picturesque. My god, she loved to show it off with her arsenal of panties and thongs hugging her well sculpted ass. It reminded me of an ass of a volleyball player, voluptuous and tight without being so big it looked fake. Needless to say, we were both very excited to actually meet.

Around six weeks into talking about what we would do to each other, I got the notice from work that I would need to travel to Charlotte for two weeks. The first person I texted was Sharon to tell her the good news, and I shared my arrival and departure date. Fast forward to landing in Charlotte about a week later, and I was in my rental car heading to check into my hotel when I got a call from Sharon. She mentioned how she wanted to meet that night, and I suggested a public place (restaurant) as to not freak her out. Her reply still makes me horny thinking about it today. Sharon said “we could do that or you could come to my house now to skip all the extra steps and give me that big hard cock I’ve been waiting for.” That got me extremely horny, and I told her to send her address.

She was a little under 30 minutes from the rental car spot, but truth be told I was actually pretty freaked out on my way over. I had never actually met this woman, and although the photos she had sent me seemed authentic, the horror stories of meet ups from dating apps had me nervous. However, I wanted this sexy woman so badly I decided To sack up and head to Sharon’s house. Nowadays I can realize I was just young and horny, but thankfully it worked out. I pulled into her neighborhood in a pretty nice suburb of Charlotte, and I parked in her driveway, being sure to tuck my visibly hard dick Superbad style into my waistband. All the fears and anxiety I had felt on the drive over were soon quelled because Sharon answered the door wearing a tight, short blue dress. She looked absolutely amazing, even better than her photos. After an introductory hug, she invited me inside for a drink.

She made us two Gin martinis, and on an unrelated note that was actually my first martini ever. We chatted in her kitchen for a little bit, both talking to each other about how relieved we were that the person behind the screen was the same in real life. I complimented Sharon for how great she looked, and how I loved The feng shui of her house. Truth be told, I had barely looked at her actual home because I could not take my eyes off the woman sitting next to me. She let out a small chuckle, and mentioned how I was taller in person than my photos. I decided to shoot my shot, and I replied with “that’s not the only thing that looks bigger in person.” Sharon let out a sultry smirk and told me how she would have to be the judge of that. After that, we leaned in and started kissing each other with some passion and intensity that was very hot. I could feel the curves of her hips, the firmness of her well sculpted muscles on her frame. I complimented how amazing her body was, and she mentioned how I have not seen anything yet. After a bit more rubbing and making out, Sharon stood up without saying a word, took my hand, and walked me to her bedroom.

She set me down on the edge of her mattress, and asked me to help her unzip her beautiful blue dress. She stood facing away from me and I gently unzipped her dress from the back, but Sharon hugged her self as to keep the dress just barely hanging on. Still facing the other direction, Sharon walked over to a dresser across from the bed, and with one hand, pressed play on the conveniently placed Bose speaker. Being a fan myself, I instantly recognized the song: Brown eyed women by the Grateful Dead. Shortly after pressing play, Sharon removed her other hand holding the top of her dress and began to bend over to takeoff the rest. She had on some beautiful black lingerie, and as Sharon turned to face and walk towards me, she told me to lean back and relax. With my legs still touching the ground but laying flat on my back on her bed, she walked right up to me and began to grind her ass all over my blatantly hard cock.

Sharon was basically giving me a lap dance to the grateful dead tune, so I wanted to sit up and reciprocate the pleasure I was feeling. The attempt was quickly denied as Sharon pushed me back, and smiling she said not just yet. At this point I just sat back, and I could begin to feel Sharon’s hands caressing around me groin and eventually right on my hard cock. She tucked my pants under the sides of my dick against my leg to exaggerate The outline and commented on how excited I was. Soon after she undid my belt and pulled down my pants and briefs, my cock flopping out as erect as I could be. We had talked in the past about how cock worship turned me on, so as soon as she laid eyes on my dick she let out an audible gasp saying she couldn’t believe it looks even bigger than the photo. Grasping it with two hands she lowered her face down to say it was bigger than her face and began to slap my dick against her right cheek.

I could not have been more turned on in the moment, and after stroking me a few times Sharon began to place her lips right on the tip of my cock. What started off as a slow and sensual blowjob quickly escalated to Sharon aggressively bobbing up and down on my cock, slobbering all over my dick and cupping and rubbing my balls so nicely. Well shit I was sucking me off, she would throw in the comments about how she loved my cock, compliments on it size, and saying how she couldn’t wait to have it inside her. I could feel myself edging to cum, so I told her to stop because she felt so good that she was going to make me cum. I told her how I wanted to taste her juicy pussy, But she simply kept bobbing on my cock keeping her lips glued to my shot. I couldn’t take it any longer, and I began to throb letting Sharon know that I was about to cum. Without missing a beat, Sharon increased her rhythm until I felt the rush of ecstasy come over me as I shot my load into her warm out. Still not breaking lip contact from my dick Sharon began to suck out every drop. When she was done, she swallowed my entire load, exclaiming how nice my big load was with a beautiful smile. I told Sharon I was slightly embarrassed that I had cum without doing anything to her, I told her how it was my turn to make her come. Laughing, she told me to not be embarrassed, for she wasn’t going to let me fuck her until I had properly cum from her blowjob. I pulled her in so she was laying on top of me for a passionate kiss, and I began to push my legs against the ground to push us further onto the bed. Sharon was light enough where I could grab her ass cheeks and lift her, so lifted her up right onto my face.

With each hand grabbing an ass cheek to spread them as Sharon sit on my face, I began to lick and kiss all around her pussy, and I was very pleased feel that she was quite wet. As I continued to eat her pussy like it was my last meal ever, I could feel quivers of her body as I began to focus more on her clit. Sharon had a nice landing strip, and truthfully her pussy looked and tasted amazing. My arms began to slide down the sides of her hips closer to her kneecaps, caressing her legs as I gently moved my hands back to grab her tight ass. I slid my hand down her ass crack just barely touching her asshole, and Sharon immediately let out a very sensual moan which I took as the green light. With her pussy pressed up against my face I began to slide my index finger gently into her asshole. She was absolutely loving it, and started to gyrate her hips. I increased the intensity of my licking and fingering. Soon she told me don’t stop, so I pushed through to the finish line until she let out a very happy and sexy series of moans. Meanwhile by this point I am already hard as a rock again, and Sharon rolled off my face and began to lie face up on the mattress. Sharon then happily stated that since we had both come from each other’s oral, she wanted my big dick deep inside of her. As my cock was already sitting at midnight, I picked her legs up and spread them so they were on either side of my head.

I teased my cock over her clit and just barely inside her pussy. Sharon sensually begged me to put it inside because she could not wait any longer. Me being a sucker for cock worship, I could not resist her begging any longer, so I began to slide my dick deep as it would go into Sharons beautiful pussy. The ecstatic moan that she let out for me going balls deep was so hot I just about blew my load right there. However, I kept it together and continued fucking her, taking my time to touch her beautiful body. I was feeling a good rhythm so I would do nine short strokes and on the 10th I would go as deep as I could. On the next round I would do eight short strokes and two consecutive deep strokes until the pattern repeated and I was fucking her as deep and as hard as I could. Sharon was going crazy in the best way, letting out borderline primal screams claiming that she was cumming all over my big cock. Knowing that I was close but still wanting to get a great view of her ass, I told her to flip over. I arched her back and pressed her face into the mattress and began to slide inside her. It wasn’t very long before my cock was throbbing and Sharon could also feel I was close. Before I could even let out a word telling her I was about to cum, she told me she needed my load deep in her pussy. That set me off and I unloaded what felt like an even bigger load than I just had earlier.

With both of us content ,I laid down as Sharon explained that she loved my warm cum in her pussy. Not too long after I asked if she was hungry, and surprisingly she told me she had already eaten. Out of courtesy I asked if she wanted to join me at dinner, and she explained that she was very content not moving the rest of the night. I kissed her good night and let myself out, smiling the entire ride to my hotel.

Source: reddit.com/r/gonewildstories/comments/uapggs/the_time_i_m_28_finally_closed_the_deal_with_a