Giving a 30yo her first creampie in wine country [MF]

So back in February, I was going stir-crazy. I was vaccinated, but hadn’t really pulled the trigger on taking advantage of that and going anywhere. I decided to check out flights, and saw I could get up to the Bay Area pretty cheaply, and found a cool place to stay in Napa. I figured a few day trip to wine country could be fun. Also, wine country tends to attract women, so why not see if I could continue to score in a road-game situation.

I ended up having some good success my first three days there, as there were a lot of women in their 40s and 50s, either doing girls trips, or, like me, doing something for themselves. Also, had a good amount of great wine, and probably joined more wine clubs than I needed to, but when you have some offsite storage, what’s a few more cases a quarter, right?

By the time Saturday morning rolled around, I was definitely feeling like the wanderlust I was sensing at home was fulfilled. The short-term nature of my planning had made it challenging to get any tastings in for that day, so I started to make other plans for my last full day in Napa.

I headed down for breakfast, finding the dining area full of couples, groups of ladies and mixed groups. Asking for a table for one, the hostess sat me in a back corner, which, given the windows, actually worked out okay for me. A few minutes later, a nearby table also got sat with a single.

She was younger, late 20s or early 30s, and tall, 5’10” or 5’11”. Light brown hair, and a really fit, athletic body. Also, just a really beautiful face. She had a notebook out and was scribbling furiously, alternating between her phone and the notebook while sipping coffee. I returned to my coffee, bacon, and English muffin, and read on my phone, as I tried to figure out a plan for the day.

‘Being here single feels like you’re a pariah, doesn’t it?’ the voice from the next table asked? I looked up and she was looking at me, awaiting a response. I said it was *very* couple and group centric for sure. We talked about our trips so far, and I mentioned that I had struck out on tasting appointments, so was going to bum around downtown Napa, work out, etc. Also shared the lightest of personal info, Alexandra, or Ali as she usually went by, was from Seattle, and worked in PR.

After a few more minutes of chatting about the area, she blurted out, ‘Would you have any interest in doing a wine tasting bike tour today?’ Apparently when this was originally booked, she had convinced her employer to send her on a wine country trip and she would ghostwrite an article for a lifestyle magazine. At the time she booked everything, it was going to be a couples guide to Napa, so she had reserved two spots on the tour. After some rescheduling due to closures, and a breakup, she now had an extra spot on a nonrefundable tour.

I decided why not, and we made plans to meet in 30 minutes in the lobby, and I’d drive us up to Yountville for the tour. When we got on the tour, we were the *only* non-coupled up riders. Still, had a great time, and Ali was a blast. We apparently gave the appearance of chemistry, and a woman in our group said something about how good looking our kids would be. All comical when you realized we met a few hours before.

After the tour, we grabbed lunch in Yountville, and between that lunch and the drive back, I learned she had done track and field in college, and while she didn’t still participate in those events, working out was her go-to stress relief. We got back to the hotel, and still had some time that afternoon to kill so I suggested we walk around downtown Napa. That walk didn’t quite turn into a run, but it was pretty brisk, and by the time we were done, we had managed to walk almost 6 miles, finding our way back to the hotel.

It was now 5:30, the sun was setting and we were standing out on the patio of the hotel watching it, drinking champagne. As we watched that, I felt Ali’s hand slip against my own, and we ended up holding hands watching the sunset over the hills, with some little squeezes and thumb strokes in between. Was definitely getting all the vibes here, and apparently so was Ali, as she turned to me and kissed me. We kissed for a bit before realizing we were in the middle of a patio with a dozen other people around us, and I suggested we get dinner.

Unfortunately, limited capacity dining meant that the hotel’s on-site restaurant was fully booked, and a quick check of Open Table and Resy said the same. Ali was a travel pro though and said, ‘Why don’t we just do room service.’ I like a girl who knows how to keep the forward momentum. We went up to her room and figured out a room service order of a couple salads, a salmon entrée to split, and a dessert.

I had picked up a bottle of champagne on Thursday during a tasting that I said I would go grab along with a bucket of ice, so ran down to my room for a few minutes to get those, and, just in case, some condoms. I returned up to Ali’s room to find her barefoot, but otherwise still in the yoga pants and sweater she had worn earlier in the day.

I put the champagne on ice and joined her on the couch in her room. We had some time before the food was going to show, so I thought I’d get us back into the mood that we were in on the patio. Watching her on a bike all day, I could see how exceptionally fit she was, and when I wrapped my arms around her to kiss her, I could feel just how fit she was. Not overly built, but the body of a collegiate athlete.

The makeout session was hot, and hands began to wander, but all of that was cut short by the knock at the door of room service. Ali answered the door and signed for the food (hooray for the expense account, although the bill itself wasn’t too exorbitant), and we began to eat. There was still a fair amount of tension while we ate, and I think we were both observing the other eating faster than you normally would in such circumstances.

When we finished up the shared salmon, Ali said, ‘Let’s save dessert, what do you think?’ I agreed, and we immediately got up from the table. She walked into the bedroom of the hotel room, pulling her sweater over her head. Underneath, she had a black sports tank/bra, similar to what you would see at the gym. I had worn a Henley, and she came to me and pulled that off of me, before kissing my neck. I reached up and felt one of her breasts through the tank, nice sized, and firm, but no signs of implants.

We sort of fell onto the bed together, her in yoga pants, and me in a great pair of joggers (side note, they can transition well from super casual, to dressy casual). Ali was not shy with her hands and quickly had her hand grasped around my cock through the joggers, stroking it up and down to full hardness. As she did, we made out, and Ali would lick and suck on my earlobe and whisper in my ear.

It didn’t take much of that before I was fully hard, and Ali kissed her way down my chest and stomach before pulling the joggers down a bit, with the head of my cock peeking out. She moved her mouth further down, licking along the line between the abdominus and obliques before running her tongue over the head of my cock. She was teasing, and in the best way possible.

I reached down and managed to pull the sports bra off. She looked up at me as I pulled it over her head, her blue eyes sparkling with lust. Ali leaned up a bit to pull the joggers further down, and as she did, I could see that her breasts appeared to have a perfect teardrop shape, and great pink, large nipples. I was now naked on her bed while she was still in yoga pants, but Ali was undeterred and started to give me a great blowjob. A lot of women struggle a bit to not scrape teeth on a girthier cock, but Ali had a fairly wide, large mouth, and seemed to be able to take the width without issue.

I could see Ali rubbing herself through the yoga pants while she blew me, her ass up in the air. After a few minutes, she pulled off and stood up to pull down her yoga pants and the thong underneath them. There she stood, all nearly 6 feet of her, C-Cup breasts with upturned nipples and just the slightest droop (ski slopes, as my friends and I would call them), taut muscular body and a triangle matt of dark pubic hair, trimmed, but barely so. I stood up to join her and then moved her back to lay her down on the bed. I started to move my way down between her legs when she stopped me and said, ‘don’t go down on me, please.’

I was a little confused, as almost *every* woman I had been with, not just this year, but ever, loves when a guy goes down on them, but she seemed to be adamant. I knelt in front of her and moved my hand down to her pussy. She moaned lightly, she clearly wasn’t opposed to me giving her pleasure, but definitely did not want my tongue down there.

We still had the lights mostly on, slightly dimmed, but light enough to see well. Ali’s clit and hood were bigger than average, and she had larger labia than average as well. I didn’t know whether she was uncomfortable with her anatomy, her grooming, or the fact that we had gone on a 6 hour bike ride and another hour and change walk at a fast pace, and maybe she just didn’t feel fresh and clean. Nevertheless, I was disappointed, as with the connection I had with her, I *really* wanted to eat her pussy.

Ali said to me, ‘I think I have a condom in my toiletry bag, it may not fit great, but we need to use it.’ I went to my pants instead, and pulled one out, tossing it to her and saying, ‘No worries, I came prepared.’ She had a big smile on her face and she told me to lay back down. She unwrapped it and put it on me, before spitting on her hand and rubbing the condom and then her pussy for some extra initial wetness.

She then straddled me and put the head of my cock against the lips of her pussy, spreading them slightly with the fingers of her right hand. Ali would push down, wince, pull up a bit, push down further, wince, pull up, and repeat, until she was pushed all the way down against the base of my cock and I was buried inside of her. Once we were there though, this was the ‘Watch Ali Ride’ show. She changed up her technique 3 or 4 times, all in a traditional cowgirl position: rubbing her clit up and down my shaft by bending it back towards my toes; twerking on it; rocking back and forth; and alternating long and short strokes. Ali could ride a cock and ride she did.

Every woman has their own way of cumming, and for Ali, it was silently breathing heavier, but otherwise not making a noise. That had happened once already when I felt my own orgasm coming, and she seemed to be well on her way to another one. She was doing the clit rubbing on my shaft, pushing my cock backwards. If you have felt that, it is great and painful at the same time, and this was no different, but it was so hot watching her cum like that. As she was climaxing, she switching to rocking back and forth with me buried deep. It was feeling *unbelievable*, and I immediately began to cum.

When I was done, Ali, pulled up and off of me and went to take my condom off when she looked down and said, ‘oh fuck, oh no, oh my god.’ I asked what was wrong and looked down and saw that the condom had completely broken and was now just a ring of latex around my shaft. Ali said she wasn’t on birth control, as she had a bad reaction to it in high school with sun exposure and immediately went off of it. She had never *not* had sex with a condom, and this was the first one that ever broke. To make it worse in her mind, she was at her most fertile time of the month, the worst possible time for this to happen.

I reassured her that pregnancy was not going to happen, due to my vasectomy. It seemed to calm her down a little, but she still seemed totally shook. We talked about STDs and testing, etc., and she seemed to finally calm enough to be able to put it out of her mind. We decided to go back to the dessert we had left earlier and finish up the bottle of champagne and returned to the couch.

When we finished those, she commented that the sex really was good, and that she was sorry about flipping out. I told her not to worry about it, totally natural. We started to make out again, sitting naked on the hotel couch. It was probably 45 minutes since we had finished up in the bedroom, and as she kissed me, and started to move her hand down, I could feel my cock starting to stir again. Ali rubbed it firmer and my cock responded by getting firmer itself.

When I was fully hard, Ali moved over to an ottoman that was in front of a chair next to the couch, and got on her hands and knees. ‘Can we try something?’ she asked me. I replied of course we could. ‘I’ve never actually had a guy inside me bare, other than what just happened. Since we’re already at this point, can we try this without a condom from the start?’ Heaven to my ears. Especially 1) knowing I was the first that she wanted to do that with, and 2) seeing that athletic ass in a doggy style position.

I moved behind her and positioned my now bare cock against the lips of her pussy, still wet with her arousal and whatever remnants of my orgasm had not dripped out onto the couch we just ate at. I slid back into her. Ali moaned, the most vocal expression she’d had that evening. ‘This feels so much better, my god.’ I wasn’t going to disagree, going bare into a pussy is one of the greatest feelings in the world.

I had a lot more stamina this time, and Ali was able to keep up throughout, as I tried to mimic the variety of strokes she had demonstrated in a cowgirl position. Her favorite seemed to be a long, slow stroke, bringing myself out to just have the head barely inside her, to then stroking it all the way back to be balls deep, and then alternating that with a couple similarly long, but fast strokes. After Ali came again, I told her I was close, just to make sure she didn’t want me to pull out. Ali said, ‘No, don’t pull out, I want you to cum in me. Cum deep in me!’

When we finished, we took a shower together, and fell into her bed. We didn’t fool around again that night, and in the morning, I awoke to her packing her suitcase. She looked a little embarrassed and said, ‘I’ve never done anything like that. I am more of a boyfriend, girl, and the six or so guys I’ve ever had sex with were all long-term relationships. I don’t really know what to do in this situation.’ I told her it was a great night and I hope she enjoyed it, as I enjoyed meeting her and spending the evening with her.

I gave her my number and said if she was ever in my city for work or vacation, to let me know. I fully anticipated I would never hear from her again given how uncomfortable she seemed by the whole situation in the morning. I threw my clothes back on and went back to my room, took another shower and packed and grabbed breakfast before driving back to Oakland to fly home. Thus far to date, as expected, I have *not* heard from Alexandra.

Source: reddit.com/r/gonewildstories/comments/qpioe2/giving_a_30yo_her_first_creampie_in_wine_country