First of all, sorry for not posting, my account was slapped with a 3 day ban for “vote manipulation.” But now I’m back and better than ever, ready to share a long requested story- how I lost my virginity.

As some of you may know from my other stories, I grew up very religious and sexually repressed due to that. Didn’t have my first kiss until 18, and didn’t lose my virginity until 20 (although I did give and receive oral sex before that.)

Well one day I was in a bar and happened to stumble across a vaguely familiar face, and very familiar ass. Jill was an art teacher in my high school whose classes I never took, but she did substitute teach me once or twice. She recognized me and laughed at how funny it was that we’d meet in a bar. She had met former students in the street before, but never in an adult setting.

Jill was short and pretty, with long dark hair, lashes, and a cute smile. She had bangs too, which seemed to suit her. Smaller boobs and a nice ass, which every guy in school had committed to memory. She was in her early 40s but looked ten years younger. Overall, every red blooded American boy’s fantasy as a hot teacher.

She was with a couple of friends but they went to play pool and left us alone (planned perhaps) and I bought her a drink. She told me about her current classes and curriculum while I told her about my college life and that I still knew nothing about art. Soon we were sitting and talking for over an hour and it just felt comfortable, seemed like a date.

Her friends left and Jill asked me to walk her home as it was after 11. I gladly took her up on that offer and about five minutes later shyly asked to hold her hand. We didn’t hug when we met so I was a little apprehensive to make contact, as it would definitely change the complexion of our fortuitous meeting. Jill just laughed at me and said “you’re so cute, I’ve been wanting to make out with you for half an hour.”

Spellbound, I just grabbed her hand and pulled her to a dark corner of the street where we kissed. Jill didn’t kiss like the teenage girls I was used to. This wasn’t aggressive kisses with a lot of tongue and sucking face. Jill kissed like an adult. Soft, passionate, slow, with her body melding into mine. She even pulled my hair and told me to “settle down cowboy” as I gave her too much tongue.

Again, I asked her politely to play with her boobs while we kissed and she quickly agreed. We slowly walked back to her place, stopping intermittently to kiss and fondle each other gently. There was no groping, in fact my hands were not allowed on her ass, and Jill forbade neck kisses. She was setting the tone and she knew it.

I dropped her off at her apartment with one last deep kiss and turned to walk away when I heard her call me- “mister” followed by my last name. I turned around and just like in school said “yes ma’am?” She smiled at me and said “aren’t you going to ask for my number?” I laughed and told her that I knew she had my number and wasn’t going to push it. Jill decided to toy with me, and for that, only gave me her email address, and said that each correspondence had to be multiple paragraphs.

Well I had to take the train back to my dorm, so I spent about 20 minutes crafting my first email to her. I told her about how much of a pleasant surprise it was to meet her, how great she looked, and I asked when she’d like to see me again. The next morning I received her reply- “U2. HMU on Thursday after 4” Followed by her number. This woman was playing games and I loved it.

As soon as my class ended at 4:30 I texted her that I had found a nice sushi place as well as a board games cafe, she could choose which one she preferred, and I can pick her up anytime after 6. I got back two laughing emojis and a short message “remember my address?” When I answered in the affirmative, she told me to come at 7.

Unsure which of the options she wanted, I parked down her block at 6:55 and walked up to the door. She buzzed me in and told me to come upstairs, where she showed me that she had a third option in mind. Jill was wearing a mini skirt and tight t shirt with a cat ears headband. She was dressed like a college girl heading to a party. “I have board games and sushi at home, sweetie.” She purred in my ear before leading me to her table which had a few rolls of sushi, a bottle of Rosè, and some of the naughtiest board games I’ve ever seen.

Jill wined and dined me while we spilled all of our secrets and fantasies. I told her about my experience (or lack thereof) and she told me about her kinks and fetishes. All the while her fingers never left my thighs or pecs, just teasing me endlessly. In fact, she pointed out the bulge in my pants multiple times, showed me that she wasn’t wearing any panties, and even went to put on a cute tail plug at one point. I was still not allowed to kiss her or touch her except for the soft kisses we exchanged between every question, and the gentle caressing of her derrière that I slipped in when she sat on my lap.

Finally she led me to the bed and told me to get completely naked and lay down. I followed her direction very quickly and did, with my hands gently covering my throbbing erection. Jill took off her top and I gazed at her B cups with rock hard nipples, before getting onto all fours and crawling between my legs.

Jill wordless looked into my eyes before pulling my hands away and watching my cock spring up. “Fuck. It’s so thick.” Was all she said before kissing the tip of my cock and licking my shaft. Everything was an art to Jill; slow, sensual kisses; all of the teasing she did; and even the slutty college girl outfit complete with a butt plug and cat ears. This blowjob was no different. I was laying back with my hands in her hair as she took her sweet time pleasuring me. The kisses, licks, and nibbles made me hard to the point I thought I was going to explode.

At one point Jill looked up at me and said “how is your first real blowjob, from a real woman?” I was too overwhelmed to respond with anything other than a moan. Finally she put my whole cock in her mouth and pressed her pretty face down until she touched my abs. I was staring into her dark bedroom eyes while she kept me impaled in her throat and lifted that luscious ass to shake her tail at me.

She remained there, holding my gaze with my dick down her throat, shaking her ass, and gently scratching my thighs. Until, as she told me later, my eyes rolled back in my head like I was having an orgasm. However I didn’t cum just yet, and it was about two or three minutes of her just bobbing down on my dick while my moans filled her room until I told her that I was about to cum.

Jill just sucked a little bit stronger, and somehow made her mouth a drop warmer while gently cupping my balls which were slick from her saliva. Her eyes and eager little moans on my cock told me that she wanted me to cum in her mouth. I held her shoulders and saw stars as I came. She literally sucked me dry, so much so that she originally was swallowing, but then gave up after ten or twelve spurts and the rest landed in her hand as she caught her breath.

Would you like part two?

Thanks for 350 followers!!