Lost my virginity to an older woman [MF]

This just happened yesterday and I just need to tell someone, so hopefully you don’t mind and maybe you’ll even enjoy it.

As the title suggests, I lost my virginity yesterday afternoon to an older woman – I think she said she was 43. I’m a 22 year old guy from NJ, though that probably doesn’t matter. I have social anxiety and I’m generally pretty awkward around people so this really caught me as a surprise and I still have to remind myself it actually happened.

Anyway, onto the story..

There’s a small pizza shop about 20 minutes away from my house that my family orders from when we wanted to pickup a quick pizza. Previously, the cashiers at the pizza shop are college students that are home for the summer looking for a summer job. Since school has started back up (mid-August?), the cashier (Christine) has been the same woman each time my family has gone there. We went there a couple of times, enough for Christine to recognize us, our names and our order.

We usually go to this pizza shop every Saturday nowadays since I come home from school on the weekends and we like to still find time to have family dinner. I usually go with my mom or dad to pick up the pizza after we call it in, and Christine has been there to handle our order for the past several times.

She’s pretty chatty and I’m pretty.. not. Christine could talk to my mom for hours and I usually just awkwardly stand there waiting to pickup our food. I noticed Christine makes a more concerted effort to talk to me and bring me into conversations or ask me about myself. I guess she noticed I’m super awkward and wanted to be polite.

Like I mentioned, we go there pretty much every Saturday and Christine is always there. It’s pretty much become routine. We go in, Christine says hello to us and starts ringing up our order in the register as we barely enter the building, then we chat a little while we wait for the pizza to be ready.

A couple of weeks ago, around the time Christine started becoming chatty with me, I noticed she would bend over in front of me often, or she’d put her hand on top of my hand when I’d grab our box of pizza, or she’d run her hand along my back if she’d walk behind me. I thought she was flirting with me but I discounted it as wishful thinking.

Well, it turns out I was actually right.

A weeks ago, I went to pick up the order by myself since my parents were both busy helping set up a bloc party in our town. I went inside and Christine greeted me as usual and asked where my parents were. I told Christine about the bloc party and asked if she would be going. She said she couldn’t because she had to work but the pizza shop she was working at was donating a few full pizza pies for their dinner. She told me she had to deliver the pizzas in a few hours and asked me if I would be willing to go with her and carry the pizzas. I initially wondered why she would need my help but didn’t think too much of it. I said sure. She took my phone number and I paid, got my food and left.

About 2 hours later I got a text from Christine asking me to come around in 30 to help her bring the stuff over to the party. I didn’t really want to be late or hold her up so I left a little early and ended up being 15 minutes early. When I got there she told me the pizzas were still in the oven and still needed a few to be ready.

She started talking to me about school and how classes were going as she was cleaning up and closed up the shop. In the middle of the conversation, while I was going on and on about my major, she mentioned she should probably clean herself up before going out and then took her shirt off and revealed a black bra. I awkwardly (and in retrospect, cringe-ly) asked her if she wanted me to go in another room while she got changed. She laughed and said no. I wasn’t sure if I was supposed to look or not look so I just took out my phone and pretended to text. She grabbed a new shirt from the pile for sale, went in back and returned with the pizzas.

As we were walking to her car, she started asking me if I had a girlfriend and I said no. She asked why and started to list off a few compliments and I thanked her and jokingly (and probably awkwardly) asked her if she had a boyfriend. She laughed and told me that she had been married for 10 years but was recently divorced. I told her I was sorry to hear that and she told me she didn’t want to talk about it and turned the conversation back to me. She asked me if I was always this shy and I told her I had an anxiety disorder, and she asked if I had ever had a girlfriend before. I told her I didn’t and she laughed and asked if earlier was the first time she saw a woman without her shirt on. I told her it was and she laughed and told me I was sweet. She didn’t really say anything for a few more minutes and I was dying in side of embarrassment and anxiety, because I’ve always been kind of self-conscious that I’ve never had a girlfriend before and I feel super judged when people ask me that.

We got to the bloc party and I carried in the pizzas to the kitchen then went back to her car. After I got in the car, she said she had to make a phone call so I was just nervously sat in her car. Afterwards, she needed a pen from her purse which was in the back seat. She opened my door and reached over me and her boobs glanced against my shoulder and I kind of jolted because I didn’t want to be impolite because.. I didn’t realize.. she was doing it on purpose. (cringe..) She asked me if I was ok and I said yeah and she asked me why I moved away. I told her I didn’t want to be in her way and she laughed. She told me I was the cutest thing and, between that and the prior convo we just had, I was fucking mortified.

We drove back to the pizza shop and she asked me random questions about like music and football but I wasn’t really able to give long answers and my voice was kind of shakey. She asked me again if I was ok and I told her I was fine and we went the rest of the trip back to the shop in silence with the radio on.

When we got back to the pizza shop, she asked me to come inside and I did. When we got inside, she asked me if I wanted something to drink and got me a bottle of water. She grabbed my hand and told me to follow her to one of the tables in the back corner of the pizza shop. She asked me to sit down and apologized for making me so nervous and I told her I was fine and she told me she could tell my voice had gotten shakey.

She asked if I was embarrassed to talk about not having a girlfriend and I lied and said not really. She started asking me questions about like what type of girl I was into and it was super awkward. I wasn’t sure if she was genuinely asking or hitting on me. It was super super awkward and part of me wanted to desperately leave and another part of me thought she was hitting on me and wanted to stay.

A few minutes later, she put her hands on top of my hands and told me that she never thanked me for helping her so much earlier. I told her it was really no big deal and to not mention it. She said she also wanted to apologize for making me so anxious and I told her that I was actually really fine. She scooted her chair next to me and grabbed my hands and placed them on her boob, and asked me if that made me nervous (it did). I told her no and she laughed and said ok. She took her hands off of mine and rubbed her hand across the front of my shorts and asked me if that was ok and I said yeah. It seriously felt like a scene out of a porno, I was so anxious that I kind of felt like I was looking at the scene happening from out of my body (is that sad?). I took my hands off of her to unzip my pants but she said “no no no” and put my hands under her shirt and told me to leave them there. She unzipped my pants and took them off so I was sitting in my boxers and was super hard. She laughed and asked “is that for me?” which I don’t really understand what she meant but I said “yep” as I continued playing with her boobs under her shirt.

She stood up and pushed the chair away. She took her shirt off and then kneeled next to me and asked me if I was sure I was ok with this. I told her I was totally fine and asked her if she was sure she wanted to do it and she said “mmhmm” and knelt down next to me and pulled my boxers down. She grabbed my dick in her hand and started stroking it and I swear I almost came immediately. She then pulled her hair back and lent forward and put the tip in her mouth and started licking it. then dropped her bra down, grabbed my hands and squeezed them with her hands on top of my hands.

I’m not going to lie, I didn’t last very long and I was super embarrassed about it. She got a towel and started cleaning up the floor as she asked me how it was. I told her it was great and she asked me if I would ever want her to do it again and I was like “yeah sure” but in my mind I was like “oh god please yes”. She laughed and said ok and told me she’d text me some time. She told me she was going to lock up and head home so I took the hint and said goodbye and left.

An hour or two later, she texted me with just a winky face so I sent her one back and she said “Im glad you liked it” and I was like “yeah you were great” which I am sure was super cringe. She didn’t respond though.

Later that week, on Wednesday, she texted me asking me what I was doing. I told her I was back at campus in class. She sent me a sad face and asked me when I would be home and I told her I’d only be home on the weekends, and she texted me another sad face. I texted her Friday afternoon telling her I’d be home in a few hours but she didn’t respond.

My dad and I went to the pizza shop like we usually do on Saturdays and she talked to us as she usually did, as if nothing happened. I was expecting it to be awkward but it wasn’t. She didn’t hint at it or joke about it or anything, and we got our food and left.

A few hours later, she texted me and told me she was about to clean up and asked what I was doing, and asked if I could “come help her lock up”. I got super excited and went there asap. I went inside and she said “well you sure got here fast” and asked if I missed her. I told her I did and she came over to me and kissed me, and ran her hand up my shirt. I decided to do the same and slid my hands up her shirt and grabbed her boobs like she instructed me to last time. She pulled my hands out of her shirt and told me not yet, then grabbed my hand and led me to the table we sat the last time. She then flipped the closed sign up and locked the door, and came and sat next to me. She told me she couldn’t stop thinking about me since last week and I told her she could’ve texted me whenever. She laughed and took her shirt off and I started playing with them again like last time. She pulled me off the chair and pulled me closer to her and slouched back in the chair, and pulled her jeans down. She told me she was already wet, took one of my hands and slid it across her panties. Then she put her hand around my neck and pulled me close to her so my face was in between her boobs. I started licking and gently biting her nipple. She kept rubbing my hand across her panties with my one hand. I decided to make a move of my own instead of needing her to direct me so I slid my hand down her panties and started fingering her. I didn’t know what I was doing so she had to teach me and it was awkward. Afterwards, she pulled her panties down and asked me if I’d like her to teach me how to eat a woman out and I was like “yeah sure” but inside I was like “awwwwww yeah”. So she did and I did. It wasn’t quite what I expected but I liked it. She told me I did a good job for a first time which I’m not sure was a compliment or not.

Afterwards, I stood up and pulled my pants down and went for sticking myself inside of her but she was like “no! no no no no!” and I was like “oh sorry”. She said “no, sorry, I can’t do that yet”
and I was like “sorry”. She instead got down on her knees and blew me again, pretty much the same as last time except I lasted like 2 minutes longer than last time. In retrospect, thank god she said no because I didn’t have a condom and that would’ve been bad.

We did the whole charade again twice more, pretty much the same as this one. We even sexted twice while I was on campus and it was super hot.

Then on Saturday, I went with my mom as we do. Again, business as usual. Like we’ve been doing, she texted me a few hours later before she was going to close up, but this time she told me to bring a condom. I had already brought a condom the last few times just in case but that text made me go from 0 to 100 so quick.

I went over and helped her clean up the counter and throw away some trash to help her finish her chores quicker. I was feeling so confident because I was comfortable with her now and it had basically become routine. Like as she would pass by me, I’d grab her ass.

Later she grabbed me by the hips and pushed me up against the wall and started making out with me. I started kissing her neck, then I lifted her shirt up and she wasn’t wearing a bra this time. I started kissing my way down her shoulderblades and down to her boobs, grabbed both of them in my hands. I pinched one of her nipples between my fingers in one hand while I gentle bit the other one. She slid her hand down my pants and started rubbing my dick over my boxers. She unzipped my pants and they dropped down to my ankles. She kneeled down and started blowing me. I lifted her back up after a minute or two and unzipped her pants and they dropped to the floor. I started rubbing her pussy over her panties. She asked me if I was sure I wanted to do this and I told her I was, and I asked if she was ok with doing it? She told me she was but she didn’t want to do it in the pizza shop (which, how unsanitary..). She asked me if I wanted to go back to her place which I nodded yes. I got in her car and we drove back to her place about 10 minutes away.

She told me she didn’t want anyone to know what we were doing which I understood, so she told me to wait until we got inside to do anything. We got inside her house and shut the door and she immediately jumped on me and wrapped her arms around me. (I was super nervous I was going to drop her LOL). We started making out as I started walking toward a couch. I lowered her down onto the couch and we both quickly took our clothes off. I took my condom out of my wallet and fumbled to put it on as she was playing with her self right in front of me which was super hot. I got the condom on and stuck my dick inside of her. She was a lot tighter than I expected. Not that I expected her to be loose but I wasn’t expecting to be such a tight fit lol. She laid back on the couch while I leaned over her, sliding myself in and out of her. I was worried about falling on top of her lol so I told her I would lay on the couch and she could ride me (always loved that in porn) but as I got up, I told her I was going to cum so she took my condom off and started jerking me off and I came in her hand. I was hoping it would be a majestic stream like in porn but sadly it was not the case. I asked her if I could use her shower before we left and I did, then she drove me back and I went home.

Anyway, hopefully I will do it again and maybe I’ll have an update. I love this sub and wanted to share now that I finally had a story lol. Sorry that I’m not a good writer. Thanks for reading. Hope you enjoyed.

Source: reddit.com/r/gonewildstories/comments/54iwvo/lost_my_virginity_to_an_older_woman_mf