[MF] How I lost my virginity at 27

The last couple of years I have been thinking that I may have missed the boat and will have to accept being a virgin for life. Being 27 is late to lose it, I didn’t like talking about it when it came up as I didn’t want it to be what I was known for.

So about a month ago I messaged an account from a sub reddit. I introduced myself and asked a few sexual questions . I didn’t get a response and wrote it off. Two weeks go by and out of the blue I get a response from the account. She answered all my questions and had a few of her own. Now in my first message I didn’t say I was still a virgin or how old I am. So im not one to beat around the bush, so I straight told her my age and how I was still a virgin and that if these were deal breakers that it was ok. Surprisingly she was more worried about my age. We messaged back and forth all evening discussing everything from why I was still a virgin to if I was circumcised. We left that night on a good note with her saying she had to go to bed and that we could chat in a few days.

The next day she messaged saying that her work schedule had changed for the following day and asked if I would like to meet for coffee. I jumped at the chance and we set a place to meet the following day. So jump to the next day I get ready and drive to the set coffee shop. I first send her a message saying I was on my way. It drove for about 20 minutes with no message from her. Think I’m going to be stood up, I exit the freeway and stop at the first light. As I wait for the light to change my phone dings with a notification. It reads simply “I’m here now”, I quickly message back “I’m a few minutes away”. As I pull into the parking lot I can feel my heart beating through my chest. “I can’t believe I’m doing this” I think as I walk to the door, and there she is at the first table in the coffee shop. Giving me a reassuring smile as we lock eyes I walk up to the table. She’s beautiful and sweet looking, all I can manage to get out is “Hi” as I sit down. She says hi back as she sips her coffee. I awkwardly sit there not knowing what to say or do, so I say “do you mind if I grab a drink?” She says no and I go up and order trying to think of something to say when I come back. I come up with nothing as I walk back to the table and nervously sit down and say ” I hope this is half as awkward for you as it is for me”. She chuckles and says “yes this is awkward but ok”. She starts with what I’m looking for and what she wants out of this. The talk is getting into some detail and the coffee shop is way too crowded for this. She suggests we go for a walk and I agree. There is a small strip mall across the parking lot and we walk over there. Talking is getting easier at this point and we discuss what I want to do and have done to me. She later tells me her hard no’s and none of them are anything I’m interested in. I ask if she was expecting anything from this first meeting as I thought it to be just a face to face meet up. She says no but wouldn’t mind making out a bit.

So we head back to my car and I drive around to the dark side of the mall and park. We kiss and make out for a while and I ask to feel her tits. She agrees and takes off her bra for easy access. We go back to making out and I’m squeezing her nipples by this point all the while keeping an eye out for security. My dick is rock hard by now and all I want to do is explore every inch of this beautiful woman with my lips,hands and dick. But wouldn’t you know it security drove by and stopped for a second. Me being nervous suggest we stop and go back to her car. Talk about a huge buzz kill but she agrees as by now I have her shirt up exposing one if not both of her breasts. I drive back to her car and we exchange numbers and make plans to meet up in a few days.

Over the next few days we text and sext back and forth and I book us a hotel room half way between us. The day comes and I’m hard all day just thinking about what is to cum. I leave work early and go home and shower. I drive to the hotel and check in I text her the address and to text me when she is here. A bit later she texts saying she was here and I go down to meet her in the lobby. As the elevator stops at the first floor the doors open and she is walking in the front door. I whistle to get her attention, she turns to see me holding the elevator. I smile as she steps into the elevator and the doors close. We start making out immediately and only stop when the doors open on our floor. I take her hand and say “let’s go” as I lead her to the room.

The second the door closed behind us we are right back to making out. She starts by pulling my shirt off and I do the same for her and fumble through taking off her bra. Her beautiful tits fall out and look amazing. She then turns her attention to my belt and pants, she waste no time and pulls my underwear down with my pants. She grabs my cock and immediately starts jerking me off as we go back to kissing.i slowly walk us over to the bed and stop. I drop and lift her sexy black skirt to expose her panties. I greedily grab them and begin working with off of her, throwing them aside as soon as I get them down. I stand and push her on to the bed lifting her skirt I’m met with the first pussy I have ever seen in real life. I soak in the moment for a second and spread her lips apart and bury my face in her wet pussy licking and sucking at what I hoped to be her clit. (This is one of my oldest fantasies, going down on a woman but I was a little worried about the smell and taste) I loved the taste, slightly salty and warm. My tongue grew tired way too soon so I began to finger her with two fingers making the come here motion and rubbing her clit with my free hand. This was amazing, the vagina opening was lower then I expected. She was so creamy and wet I took my fingers out and sucked them clean. She sat up and said it was my turn. By this point I was ready to cum just from the excitement but we trade places on the bed and she removes her skirt. She jumped right in taking ahold of my dick and wrapping her amazing lips around the head of my dick. I’m all ready in heaven and then she starts using her tongue and hand. I’m almost there already, telling her how good this feels. Only a few more head Bob’s and dick squeezes and I’m telling her I’m going to cum. She continues sucking my dick all through my orgasm and after. She swallowed my whole load and didn’t even flinch. I still laying there twitching like some kind of seizure case. She just smiles and continues to play with my dick with her hand. I thank her for that and how hot it was that she swallowed my cum. She says it was fun and keeps playing with me till I’m hard again. I put on a condom and we fuck cowgirl and then doggy. Slipping out every few pumps and losing our rhythm, but having fun all along. I cum again fucking her doggy and collapse on the bed beside her. After cuddling for awhile she starts touching and rubbing my dick hard again. She then proceeds to give me the best orgasm of my life with her mouth swallow my cum all over again. I mean this orgasm was Earth shattering my hands went numb.

To cut this short we had a lot of fun that night even though I didn’t get her off, and we agreed to meet again a couple days from then. I’m so thankful for this amazing woman for guiding me through this mile stone event, and made me feel comfortable.

Source: reddit.com/r/gonewildstories/comments/e0vdf7/mf_how_i_lost_my_virginity_at_27