In response to a question about some favorite hookups in the year, I shared this story about No. 92, Arielle, on 4.10.2021. Concerts had just sort of re-started up in March, but it was still very much an atypical concert experience, with long lines to get in, mask requirements, etc. This was the second concert I had gone to since things had been re-opened, used to be something my ex and I would do regularly. I was standing in line to get a water, and when the girl in front of me got to the front of the line, she realized that it was a no-cash, card only situation. I could tell she was about to get upset about it, so stepped in and said they could put her beer on my card. She said thank you, and went to hand me the cash, and I said not to worry about it.
I got a good look at her, not really my type. 5’1″, chubby, probably around 175-185 pounds. Blonde hair and an average face from what I could see with the mask obscuring her nose and mouth. On a scale of 1-10, a 6 at best. We went our separate ways and listened to the opener. After their set finished, she came over to me to thank me again. She had the mask down as she was drinking her beer, and my suspicions of her being a 6 were confirmed. Nice personality though, and we had a good chat before the headlining band came on. She had good energy and was sort of dancing/jumping. I saw she finished her beer and asked if I could get her another. We went up to the bar together, and I got another water, while she got another beer.
The headliner was good and played pretty long, and we actually got another round mid-way through their set. Her dancing was pretty infectious, and I started to move with her too, which was fun since going to a concert by yourself can sometimes feel awkward. She even grinded against me a couple times, although with our height difference, it was more of her ass grinding against my thigh.
After the concert, she asked if she could return the favor and buy me late dinner/drinks, before catching herself, not knowing whether I drink at all (which I do). I said sure, we could do that, and we went to look for someplace nearby. All the places we found had shut down by that time, and she asked if I wanted to just get a drink at her place, since she needed to relieve the babysitter anyway. So, we got an uber and went to hers. On the way, talked to get to know each other a little more. She was a bank teller, had a 9 year old daughter, she and the dad were dating at the time, broke up while she was pregnant. This concert was the first thing she had done from a going-out perspective in a little over a year. We got to her place, receiving an eyebrow raise from the babysitter. Arielle grabbed two beers from the fridge and then went to make grilled cheese sandwiches. We ate those and talked a bit more, until there was a pause in the conversation, at which point she got up. I thought she was going to take the plates back to the kitchen, but she moved back on the coffee table, sat down on it right in front of me and then grabbed my shoulders and pulled me in for a kiss.
We made out for a few minutes when she pulled her shirt over her head. Fairly large breasts in a full coverage bra, would say she had somewhere D or DD, but a large band size as well. She then grabbed my hand and led me to her bedroom, peeking in the room next door to make sure her daughter was asleep.
Once we were in her room, she lost the bra. Her breasts were large and had sagged a little. She then pulled off her yoga pants and was just in a pink thong. I meanwhile was still totally dressed. She took action on that and pulled my t-shirt over my head before unbuttoning my jeans and starting to pull those off. I stopped her and took off my shoes and socks so she could actually get them off. She then pulled me briefs down as well, and remarked that I had a great cock, before reaching down and grabbing it.
I assumed she was going to drop down and give me head, which would be the next thing that would happen in this situation 99% of the time. Instead, she pulled me over to the bed, and continued making out with me, while just holding my cock, not even stroking it. I reached my hand down to her thong and started to slide underneath the waistband. She was shaved and had a coinslot vulva. I slid my hand further before she stopped me and said she was on her period. I’ve done stuff with girls on their period, so wasn’t put off or anything, but she didn’t feel comfortable doing anything.
I really wasn’t sure where this was going to go, she had taken charge, and brought us in here and got us naked, but then didn’t seem to want to do anything of the things two adults do when naked in a bedroom. I decided to ask if she wanted to give me head. She replied, ‘absolutely not, I hate blowjobs, I cannot do that.’ Okay, so that’s out.
We made out some more, her still just holding my cock, me totally naked and her still in her thong. Imagine my surprise then when she pulled her head back and said, ‘Would you be okay with anal?’ I said I was, and she went to her bedside table and grabbed a small bottle of lube. I asked if she had any condoms we could use, and she said she was fine if I wanted to go bare, since we were doing anal. Her nonchalance around the STD risk was a little surprising, but she said she hadn’t been with a guy in over a year, and was clean.
She took off her thong and laid on her back and had me finger her ass for probably 15 to 20 minutes, starting slow with one finger before going to two. I applied quite a bit of lube to my cock before positioning it at her asshole, with her on her back at the edge of the bed, feet up and on either side of her ass. When I started to push in, she commented that she’d never tried with a cock this thick. It took quite a bit of effort to get the head in, and once it was in there, we still took a fair amount of time to work the shaft into her. Arielle let out a couple soft moans.
In this position, I could finally get a good look at her shaved pussy. When her legs were spread, the coin slot appearance from the front wasn’t as prominent, instead, I could see her labia, which were longer and spread out in an almost diamond shape, with her rather large clit becoming more pronounced and accessible. In the modified missionary position we were in I couldn’t quite get all the way in, and after several minutes of pumping her ass in that position, I asked if she would get into doggy. When she did, her rather plump ass pointing up at me, I pushed back into her.
From behind I could get deeper, and eventually was all the way into her, my balls slapping against her pussy when I started to quicken my pace. Arielle had buried her head in a pillow, her whimpering getting louder. She didn’t want to wake her daughter, so she needed the muffling effects of the pillow as she got her ass pounded while she rubbed her clit.
She ended up cumming, and then asked if we could change positions again. She had me lie down, and then got on top to ride me. I was impressed by how much her ass could take, especially given how long it had been since she had been with a guy and the thickness of my own cock. Arielle was alternating between rubbing her clit against my pubic bone, and then leaning back and doing long strokes, giving me the opportunity to rub her clit myself.
After several more minutes, I could feel my own orgasm reaching the point of no return. I told her as much and assumed she would hop off and have me cum outside of her. Once again to my surprise, she actually went harder, and as my cock began to twitch, she pushed all the way down, pushing my cock deep into her when I came. She pulled off of me, with some cum spilling out.
I used her bathroom to pee, and she was going to take a shower when her daughter knocked on her door wondering what the noises were. She got her back to bed, and I told Arielle I needed to head out. We didn’t even exchange numbers or anything, and I texted the FWB I had on backup that I was too tired for the night and we needed to reschedule. I then took an Uber home and fell asleep. I slept pretty hard and ended up oversleeping. I was woken up by my doorbell ringing, where another fuckbuddy I had seen a few times had come over (planned, not spontaneous). But that is a story for another time.
Source: reddit.com/r/gonewildstories/comments/qyg0qo/the_one_with_the_chubby_single_mom_and_the