So, I live in a smallish town (sorta) its like on 30 thousand people.
So, as the title says, I jerked off with my Highschool teacher. I know the age is a little weird, almost a decade but honestly I don’t care lol.
Anyways, my old highschool teacher lives only a few blocks away, which was handy for this. Honestly, it started when I reached out to her for a reference check for a summer job while I was in school, just a job at a local coffee shop so whatever. After I sent her an email she asked I reach out to her via her cell going forward since this wasn’t strictly college related and she gave me her cell, while also saying to go ahead and put her down as a reference. So I sent her a text with my name so she had my number as well.
About a week later she reached to let me know they had called and gave me a great reference! I said thanks and we made some small talk about school and stuff. About a week later I wondered I had saw her come through the drivethru of my coffee shop (common one in my country so nothing crazy) so when I was on break I sent her a text asking, she replied saying she had. We talk a bit more then she asked for a pic of me in my uniform! Honestly, I wondered it was weird but I said OK and took a pic in the bathroom mirror and sent it to her. She said “You look so cute in it!” Which again I wondered was a little flirty and weird but wondered nothing else really of it.
I got off my shift a few hours later and I headed home. Around 6PM I get a text from her again and this time it read “Hey congrats on your first day, I hope you enjoyed it!” So I sent back a message saying I had and I appreciate her hyping me up! We talked a bit more back and forth and then I said I had to go take a shower and head to bed due to work in the morning. to which she replied, “OK have fun!”
Another few days went by and I saw her come into the store this time and come to my til area (I’m not the cash but we all have our own little areas for coffee) Anyways, I quickly said hello and I upsized her drink for free and put a little “good to see you!” on the drink with our marker writing thing we have. When I went on break I checked my phone and she had texted me “Loved the message and thanks for the large drink! I owe you one!” I replied saying it was no issue at all it was the least I could do since she gave me such a good reference! to which she replied “You’re so sweet!”
About a week later she reached out asking me if I had any idea what was going on with her computer. (I’m in school for computer science). After about 30-40 minutes of trying to help her via text and ft she asked if I could just come over and take a look. I got her address (which is when I found out she lived sorta close) and said I’d come over now.
When I got over there she brought me to her office room. While I was trying to fix her computer (which I managed to fix btw, it was a driver problem with her sound card) She sat beside me and chatted. I do not know why, but I got a boner. honestly I don’t remember being horny, I was focusing on fixing her computer but I got one none the less. I only noticed when I got up to leave after fixing the computer and noticed. I said nothing about it and left. She thanked me and gave me a hug. about 2 days later I texted her asking if her PC was working fine still, she said it was. She then asked something along the lines of “you really like fixing computers huh?” I asked what she meant, to which she said “Well.. I hugged you at the end and well”. I immediately felt my face flush and after about 3 minutes of being super embarrassed I responded “I’m so sorry I don’t know why it happened” She responded “Its OK! I wasn’t offended!” I sent a text apologizing again and then I went and sat in my room mortified for easily an hour.
The next day she sent me a text that said “Seriously don’t feel bad about it! I know you didn’t mean anything bad by it OK?” I waited until later that night out of sheer embarrassment and then respond “I’m really sorry!”. She texted back right away “It’s totally fine! My computer works great again you did a good job and nothing wrong!” I sent back a message saying sorry again and thanks. After about 20 minutes she sent me another one saying “I know you’re embarrassed but can I get you to come look at my iPad? It’s acting really weird today and wont charge” after a few minutes I said OK “Give me 15 minutes and then I’ll head over”. I went and jerked off this time. Honestly I was so embarrassed I did not want to get a boner again.
about 2 minutes later I got to her house. She greeted me and gave me a hug right away and said “Hey good job! I didn’t get stabbed this time!” My face LIT up red, I know because I could feel it and she laughed really hard. She grabbed her iPad and handed it to me. her background was a picture of her on vacation taking like a vacation selfie from like top angle down sorta thing. I tried to ignore it but I started to get hard. (Shes hot, sue me). I took a look at the ipad settings went into battery health, it said it was fine blah blah it was just a bad power brick. Grabbed her a spare power brick from my backpack and voila! She thanked me again and offered me something to drink. I (still with a boner) said no and she said oh okay no issue! And gave me a hug again before I could say no. She stepped back and said “Oh, there you go again stabbing me!” and laughed. I, in total embarrassment said to her “I’m so sorry! I even jerked off so this wouldnt happen”. Immediately I realized what I said and just got so embarrassed. She laughed even more and said “It’s totally fine! You like computers A LOT I guess!” “I gave a little laugh and said yeah absolutely!” The she said “Well, I feel bad I keep embarassing you!” I said no issue, thanked her again and left.
When I got home I went to jerk off again and to my surprise she had sent me the photo that was her ipad background and a text that read “I feel bad! Heres my apology! Have fun!” I don’t think I’m totally an idiot so at this point I caught on that she was probably flirting with me. So i sent back “Damn, thanks, this helps a lot ;)” She sent back a “It my pleasure ;)”. Then I jerked off and came a crazy amount. usually I just catch it in kleenex, but that wasn’t enough.
About 3 or 4 day went by and she sends me another text “I’m so sorry this is the last time I promise but can you come over and help me again? My computer started doing the same thing as last time” I said OK sure I’ll be over in a few minutes to which she replied “Don’t worry about jerking off you weirdo ;)” I got red again for sure and of course was now horny. I get over there, she shows me into her office again and sure enough it was a sound problem again. After I fix it she moves me and the chair over and says “I want to show you something really quick as well!” I said sure. She goes into photos and pulls up vacation photos album and starts just going through her vacation album commenting on them and such, it was cool and we made some conversation about it. Then she gets to about 15-20 bikini and underwear photos and starts showing me them. I’m immediately hard again. After going through them and explaining the “story” behind them she laughs and says “Well thats all I wanted to show you!” I’m horny as fuck now of course and I lean in and grab her hand and pull it to my boner. She laughed and pulled back and said” Not so fast, lemme see it!” I pulled down my pants, took off my underwear and let her see my boner. She got a little red and said “Jerk off”. Shocked, I said “really?” she said “yes, jerk off for me”. I’m not thinking anymore I’m so horny, so I jerked off. After about 2 minutes she said “Cum for me, don’t worry about the mess let me know when you’re close”. After about 3 minutes I said “I’m close.” she got down on her knees and I blew my load on her face and in her mouth. She yelped and laughed. Then we both cleaned up, she gave me a hug again and I went on my way”
The next night she sent me a text saying “I have to have more computer problems ;)” and I sent back “Don’t worry I can fix you up”. She responded with “;)” and a picture of her boobs and said “Want to come over again?”
I’ve done this about 6 times now. The last time she touched herself at the same time. I’m losing my mind thinking about it and honestly it’s all I think about when I jerk off now. We sext back and forth a lot as well.
I love it.
NSFW: yes
luckiest guy ever imo