Thank you all for enjoying part one and your wonderful comments and messages. I apologize for the delay with part two, but now it’s good to go! If you haven’t read part one yet, please do so before reading part two.

Jill and I went out probably a half dozen more times before going all the way. There was no rush or pressure: she lived close by, was available almost every night, and was a lot of fun outside of the bedroom too. We’d go to all kinds of nightlife, and spent plenty of time walking together, but each date inevitably ended up in her apartment with both of us having multiple orgasms.

Jill was an artist at heart, and oral sex with her displayed that more than anything. As you know, her blowjobs were magical and erotic. But eating her out was like a gentle and sweet dance between my mouth and her vagina. She also had lasered from the eyelashes down, with just a small thatch of brown hair above her kitty, like an upside down triangle pointing to her clit.

I remember the first time I ate her out, how soft and gentle she wanted me to be. Her tiny feet just rested on my back as the tip of my tongue daintily manipulated her clit until she threw her head back in ecstasy. I don’t have a super long tongue and definitely got a cramp or two which meant taking a break to suck all of her juices and move my jaw around before spitting it back on her pussy.

Jill had thick, clear grool and it would make a mess of her thighs if I wasn’t there to clean it all up with my tongue. Which takes us to the time I lost my virginity, we’d been talking about it and I was ready go, pretty much chomping at the bit to fill up her tight pussy with my throbbing cock. We were supposed to go out for dinner one night, but when I got to her place, she came out in a bathrobe having just taken a shower.

Jill gave me some wine and asked me to wait in the kitchen while she got ready. I gladly complied and just relaxed for about twenty minutes. When Jill came out to fetch me, she was wearing a full face of makeup and nothing else. It was most definitely go time. I stood up and she jumped into my arms to kiss me, so I held her sweet ass while carried her right back to her bedroom.

I was wearing a button shirt and chinos, but in seconds she had me down to my underwear as I was on top of her, kissing her and grinding my throbbing erection into her abdomen as she wrapped her legs around me. Between her pussy juices and the pre cum leaking out of my dick, my boxer briefs were full of wet spots. When I went down to try to taste her, Jill pulled my hair and stopped me, she wanted me inside of her.

She had condoms and I put one on, wondering if the tightness was going to help or hurt my erection duration. (It took another year and a bit for me to realize that I need the magnums, and tight condoms are not pleasant at all.) Jill was just laying on her back, ass on a pillow, and I vividly remember leaning over her with her legs on my shoulders. Staring directly into her eyes as she gripped my left forearm while my right hand slid the head of my cock up and down her tight pussy.

Jill squeezed my arm and said my name “do it sweetie, Mommy wants you inside of her.” I didn’t have a mommy kink before, but damn was that hot to hear. With those words, I slid the head of my cock inside of her tight pussy, and used my body weight to push myself inside of her. Inch by inch, I slowly filled Jill’s tight kitty, with my hands on either side of her body, as she squeezed my forearms.

I felt my hardness fully penetrate her, my penis was deep inside of where it had always yearned to be. There was a rush of emotions, but they were all overshadowed by one prevailing thought- DO NOT CUM. I couldn’t feel how soft she was, but she was so warm and tight. Jill had put on some coconut oil as lube, and my strokes soon became fluid and rhythmic. I didn’t think I was going to last more than a minute, but somehow I managed close to ten.

It must’ve been a combination of nervousness and the condom dulling sensation. But when Jill embedded her nails in my back and let out a very womanly moan, I knew there was no chance of holding back. Her pussy clamped down so tight that I couldn’t pull out mid stroke. Resigned to my fate, I rested my body weight on top of her, kissed her neck, and held her tight as I came while inside of her.

Awash in the afterglow, I could barely hear Jill asking me how it was. I had become a man. I had lost my virginity to my 40 year old teacher, made her cum on my cock, and then came while she dug her nails in my back. And Jill wasn’t done yet, not with the mommy kink, not with the passionate sex, and not with making me cum.

We kissed and cuddled for a bit until I got hard again, and then Jill asked me which position I wanted to fuck her in next. I immediately said “doggy” which made her laugh but she quickly got onto all fours and wiggled her ass in the air. I put my hands on the curve of her hips and slowly pulled her into my stiff rod, while spreading her cheeks and getting an eyeful of her pinkish brown pucker.

I thrusted into her, gingerly at first, until she told me to use her as hard as I wish. It was my second round of the night, but spitting on her pussy as I fucked her, combined with a few spanks and pounding her tight pussy as fast as I could, meant I was not going to last long. And I didn’t, probably a minute or two after I finish spanking her supple ass, and just focused on holding her hips as I fucked her, I filled up a second condom on the night.

Jill thought that was going to be it and put on some pants so we could cuddle and watch something, but having her as my little spoon made me hard as a rock again. This time, she wanted to take control and told me to lay on my back with my hands holding the slats of the headboard. She then used her mouth to put the third and final condom in the box onto my almost fully hard dick. She finished sliding it down my shaft with her hand and told me to keep my hands planted on her headboard- there would be no touching this round.

Jill climbed onto my now full mast pole and slowly sank down, completely in charge of the depth, speed, and tempo. I was aching to grab her bouncing boobs and play with her nipples as she rode me. The thought of reaching around and pulling apart her ass cheeks didn’t escape my mind either, but she must’ve seen the look in my eyes because she reminded to keep my hands where they were. Jill asked me how much I liked mommy’s tight pussy as she rode me, all the way up and all the way down.

Everything out of my mouth was “yes mommy” or “fuck mommy that feels so good” and I could tell she was giving me a new kink. Finally, when she leaned forward and placed her hands on my pecs before changing from an up and down motion to just grinding on me, I was ready to blow my load again. Jill didn’t seem to be particularly close but she just stared into my eyes and pushed her hot sex down further into my pubic bone. “Cum for mommy” she said a few times, using my name in every sentence, “cum hard for me, my sweet boy.”

With that, I was so far over the edge, there was no coming back. Jill ground her pussy into my pelvis as I came for the third time, both of our moans filling the room. She stayed on top of me while I softened inside of her, just kissing and touching her clit. Again I came without her, and again she told me not to worry because it was my special night. But I was determined to at least end the night with an orgasm from her, so as soon as I caught my breath and got some water, I played with her clit.

We just laid next to each other and synchronized our breathing while I teased her pussy and touched her all over. But soon, Jill had her hand on my cock and was slowly stroking me as well. I wanted to go for another round, but she had only cum during missionary, so missionary was chosen again. Again, Jill placed the pillow under her soft ass and helped guide me between her spread legs, to her dripping wet sex which was already too sore for deep strokes. So I just laid on top of her and we decided to just grind into each other with my cock inside of her.

Artsy forever, this was like a dance, no pounding, no thrusting, my dick barely came out of her pussy. Just grinding, so my pubic bone teased her clit while her pussy was filled with my overworked and overwhelmed little friend. And again, with her nails dug deeply into my back, Jill came hard. She moaned directly into my ear and told me how good I felt inside of her. I was on my fourth round and about as close to heaven as possible. I let the moment wash over me, the sounds, scents, and feels- and then I came too.

Thank you for 550 followers! I hope to post twice a week until I run out of stories, so please let me know if there are any kinks or fantasies you have… if I’ve experienced them, I’ll write about it next :)