40 [M4F] #Phoenix - [SUCCESS] - A kind woman helped me lose my virginity days before my 40th birthday.
For far too long, I had a complex about being an older virgin. To say I was frustrated would be a bit of an understatement. But I pushed on, made posts on just about every subreddit I could think of to help widen my net on finding offers. r/RandomActsOfMuffDive , r/RandomActsOfBlowJob , r/dirtyr4r , r/VirginityExchange and so on. Weeks turned into months into years. Sure I would get offers, but something would always stop the plans. Either the conversation would fizzle out, or I would get ghosted, or we couldn't get the logistics to work, or it was me simply getting cold feet due to a lifetime of mental health problems. All of that changed last week.
I was doing my usual checking up on this account when I saw a DM from a woman we'll call M. She had a simple proposition, she was driving through the area on work business and asked if I wanted to meet up at a nearby restaurant to get to know each other. Part of me wanted to back out, to simply embrace being a failure, but nothing happens if you don't put in effort, so I nervously accepted her offer and met up with her. We had a good 30-45 minute conversation while she sipped on a hot chocolate and I sat there extremely nervous when I hear "Do you want to get out of here and head to your place?"
My heart raced, this was it. In a matter of hours I had gone from accepting my fate as a 40 year old virgin to receiving one of the most wonderful birthday presents. I get back home with her right behind me in her work vehicle and we head inside. There we sit on a couch and slowly become more and more intimate. First simply sitting together talking, then her leaning on me, then her guiding my hands where she wants them. My hands were clearly having an effect on her as I started exploring more and more of her body. First her upper thigh, then around her breasts, until I finally started massaging her nipples.
At that moment I realized what was actually happening. This whole time she was feeling my hard cock through my pants knowing how much I wanted it and that was her cue to remove her top. When I saw her breasts for the first time, I instinctively got a mouthful and started suckling on her nipples. Ladies, if you want me to be happy(and make you happy at the same time) I love to suck on titties and to finally experience it, I went all in. Sucking on her hardened nipples, I used my free hand to go for her panties and start rubbing her pussy through them.
Minutes passed and she was getting wetter by the second until she spoke up and said "Let's move this to the bedroom. We awkwardly shuffled to the bedroom to continue the fun. Having full access to explore and embrace her pubic area. Kissing her thighs and massaging the general area to get her in the mood even more. Mind you, I had 0 experience with a woman before tonight, but I felt like I knew what to do. My focus was on making her feel good. Eventually she had fully stripped, and there I was seeing my first pussy in person. I gently brushed it with my fingers and slowly lowered my mouth onto it. First licking the lips, then circling her clitoral area with my tongue, slowing down and speeding up as she asked, until I eventually stuck my tongue inside.
The taste was not what I was expecting, but experiencing the taste of a woman is what any man should strive for and I enjoyed the taste of her pussy. Getting mouthful after mouthful, my tongue moving where she wanted it, and then I heard "Give me one of your hands. Let me suck on it so you can finger me." So I did just that and with my fingers lubed up from her mouth, I got to feel inside her and experience how warm and wet she was. I had done this to her and for her. There was a naked woman in bed and my mouth and fingers were covered in pussy juice. I then asked her a simple question "Can I put my virgin cock inside of you?" And she said yes.
Now granted with all first sexual encounters, nothing goes perfectly, and when it came to stick rod in hole, I had a bit of performance anxiety. Maybe it was the medication I was on, maybe it was the years of porn and hentai messing with my levels of horny, maybe it was the lifetime of mental health problems, but I had a bit of a struggle staying hard. But she was kind and reassured me that it's normal for that to happen. So even though I didn't get to cum inside or on her, we spent the rest of the night exploring various sexual positions(She particularly liked when I went doggy on her while she was leaning on the bed). Eventually dawn broke and we were both exhausted, sleep deprived, and happy. We got our clothes on and I escorted her back to her car and made sure she was off safe and sound.
Normally that's where the story should have ended, but I noticed she left her sunglasses behind. So I messaged her the next day and asked if she wanted them back "and a little more ;)" I added. She was more than happy to oblige me a second night and so we had a few more hours of fun together. This time actually managing to cum using a position I had always wanted to experience, a Nursing Handjob(it's where you jerk off the man while he sucks on your boobs). What can I say, I love breasts. So, in closing, that's the story of how a shy nerd lost his virginity right before turning 40 and had one of the best birthdays ever.
And if you ever read this M, thank you again. You gave me some of the happiest nights of my life.
Posted May 11, 2025, 8:05 PM UTC