[MF] Losing my virginity to older married woman…sort of

Tonight was the night I had been dreaming of for 25 years of my life. On a last ditch effort to find something to do tonight, I texted Beth. I had made a post on Craigslist a couple of weeks ago looking to please a woman/get her off as much as possible. Beth was the only response that wasn’t a robot in the few posts I have made on CL over the years.

We chatted a bit for a day or two between the time I posted the ad and I finally met up with her (tonight). Nothing seemed to come from it, and she seemed standoffish, like we would never actually meet. She had sent a couple SFW pics the first interaction, and we did a bit of dirty talk, but it never went far.

So today, I texted her and asked if she wanted a drink. She had mentioned a drink or two gets her handsy and loosened up, so I figured this was a good offer. We did some dirty talking, and she sent a couple NSFW pics while talking about how wet she was.

I was still doubtful we would meet today, and went to pour a drink. I got a sip in when I was graced with the message that she just needed to freshen up and wanted me to pick her up at a 7/11 that was 15 minutes from me.

So, I put my drink down, hopped in the shower, vaped some wax, and was on my way to pick her up. She asked what kind of car I had, and I even showed up a few minutes early to make sure this wasn’t a scam/setup/mugging waiting to happen. I circled the place a couple times, then told her to come out, and drove in.

To my surprise, she was real. The woman in the pictures, and she was alone. She texted to ask if it was me, and then got in. I told her I didn’t have any condoms, and she went in to get some.

We just made small talk the whole ride home, which was effortless despite the age gap (which was 10-15 years). She was fun, sassy, sarcastic, and giggly. We went inside my house, and I offered her a drink. She just wanted water and didn’t want to deal with me making a drink.

We walked upstairs to the balcony/bedroom thing because my house was empty, but my brother was supposed to be home in an hour or two, and I didn’t want to worry about noise.

It’s all kind of a blur, but we eventually sat down on the bed, then laid down. After making out for a few minutes, I asked if she could take her shirt off, which she obliged. She had massive tits (which I later found out were 40 D’s). All natural, and huge with small pale nipples. Not very long/prominent nipples, and well over a handful each. She was 5’3, with small hands, those huge boobs, a short hairdo, and a giant ass (which will come into play later).

After getting her top and bra off, with her straddling me, we continued to make out. Throughout our 3.5 hours together, we did lots of cuddling, holding, kissing, head resting, teasing, and talking. It was a very intimate evening. I found out she was married since HS, hadn’t been touched in over a year, and I was the first person she cheated with.

She blew me, but had tons of teeth. Like it actually hurt the first few seconds until I said something, then it still hurt whenever she was blowing me. She blamed it on my girth, which I’ll take as a compliment. My dick is only like 5 inches long though, which combine with her massive ass was an issue. I fingered her and went down on her to make her cum twice. She got very wet, very easily, which was a huge turn on for me.

At one point, I asked her to grab a condom. She got one, put it on me, and blew me for a few seconds. The teeth hurt through the condom even. She then got on top of me, and after some struggling, we got my dick in! Sweet baby Jesus did it feel good and warm in there.

After grinding back and forth for about 20 seconds, it popped out. We rearranged, but given that we’re both pretty big people and it was a twin bed, it was tough to get in a good position. I pulled to the end of the bed, but my dick was so soft the condom was falling off. I ate her out again to try to get hard, but we decided on cuddling and making out when that didn’t work.

Got hard and tried to put it in again. However, it was at this point I found out she was married and her history. She told me I could go without a condom because she couldn’t physically have kids and had only been with the one guy for almost 20 years.

So we tried, with her on top of me again, then spooning, then missionary. All with her stroking my dick, teasing me, and making out with me in between. At one point, she asked “what” because I must have had a dumb grin on my face, and I just said I was nervous. She asked why, and I told her it was my first time. She exclaimed “Oh my god”, and I thougt it was in a bad way. She just said she didn’t want to fail to live up to any expectations or anything, but that it was fine. We kept trying, but my dick would get hard for a minute or two, then go down like a Kamikaze.

God forbid I ask her to blow me and scrape my dick raw, so we decided to call it a night. I got her off two more times, and the last one she squirted a fuck ton. Still haven’t checked the sheets on our guest bed, but I’m guessing they’re going to need some oxiclean.

She went pee, and we got dressed. I drove her home, and of course the music wasn’t working on my phone, so there were some silences. Dropped her off in the same parking lot, kissed her three times, and she got out. When I pulled out, she looked up from the crosswalk to wave to me.

She’s in town for another week or two, but I’m not sure anything will come of it. She felt bad for not getting me to cum, which I told her was my fault, not hers (true). I have high blood pressure and a porn addiction. I’ve only been with one other girl, and she couldn’t make me cum the first time we were together either (handjob or blowjob). I hope I get a chance to see her again, though I don’t know that I would bring her to my house again. My brother got home, and I had to walk her down the stairs and past him to get to my car. (“Hey, I know I’m a completely introverted recluse, but ignore that late 30’s woman walking down the stairs behind me at 1:30 AM, our sweaty hair, and the smell of latex.”)

So now that I’m 25, and I finally lost my virginity tonight (kind of), it seemed to be a lesson more than anything.

1. Did the pussy feel good? Of course, it felt amazing. Pretty good with the rubber, and ohmygodwhere’smyface without it. But my hand feels pretty good with a gob of coconut oil and some peppermint essential oil for that tingle. I greatly preferred the physical touch of another person’s skin, as well as the fact that she cared about me (for the night at least). To feel wanted and like I was completely content was something I’ve never experienced (sans psilocybin).

2. I’m really glad I waited and didn’t pay to lose my virginity

3. There are real people on Craigslist that aren’t robots

Source: reddit.com/r/gonewildstories/comments/5a5bnt/mf_losing_my_virginity_to_older_married_womansort