My first real girlfriend was much more sexually experienced than I was, and it intimidated me more than a little bit. Bobbi was a year older and I considered her out of my league, but one night while we were at a party heavily drinking, I got the courage to ask her out, and she said yes. The next day I gave her the space to walk that back, but she said she liked me too and was happy that I asked her. For the first month or so, we did little more than above the waist or hand stuff, and though I desperately wanted to sleep with her, I was nervous I wouldn’t last. She’d become my first.
We first had sex shortly after my birthday a few months into dating, and true to form, I lasted about 30 seconds, though I was ready to go again in about another 30 seconds, and lasted closer to three minutes that time! I was borderline mortified, but Bobbi was gracious and never mentioned it. Each time we’d sleep together, I’d spend more and more time on foreplay, knowing that I needed to make her cum before we had sex in case I didn’t last long enough during sex.
Eventually, I gained more confidence and stamina, but I also really developed an affinity for foreplay, especially eating her out. I loved taking my time with her and teasing, gently getting her closer and closer to cumming, then easing back off; sometimes spending 10 minutes on one breast, or kissing my way down her body slowly, skipping over her panties, and kissing down her legs, only to do the same in reverse on my way back up.
The longer I took teasing Bobbi without touching her pussy, the wetter she’d get, oftentimes soaking right through her panties. I knew it drove her wild, and I always loved peeling her wet panties away from her lips to see the strands of shiny grool stretching between the two. After sliding her panties down and off her legs, I’d part her lips and give one slow long lick from the bottom of her pussy to her clit, filling my tongue with her juices, before starting to eat her out in earnest. After she’d cum, we’d have sex, and the time I spent going down on her would usually desensitize me enough to last a good bit of time, and we’d both be satisfied.
One night we were at her parents’ house after they had gone to bed. We’d been teasing each other but knew it couldn’t really go anywhere because we had no condoms. She got ruthless though, reaching into my boxers and swirling my precum around the head of my cock, telling me how badly she wanted me. It was shortly after midnight, and I couldn’t leave her house to get condoms and come back (her father had installed some kind of alert system that beeped in their bedroom when the motion lights were triggered so he knew when his daughter was home). I lifted her up onto the counter and pressed my face into her crotch over her grey sweatpants. I could smell her pussy and I needed to eat her. It was the first time I confessed to how much I loved eating her out, how I needed it, right then. While she was skeptical, she quietly led me upstairs into her vacant older sister’s room, which was furthest from her parent’s room, down the hallway, around the corner, instead of her bedroom, which shared a wall with the master.
Bobbi lay down on the bed and I climbed on top of her, kissing her voraciously. My hands were groping and massaging her tits and I was kissing her neck when she said, “show me how much you love it…” I knelt between her legs, grabbed the waistband of her sweatpants, and pulled them down and off her legs in one motion, leaving her legs on my shoulders with a view of a large wet spot on her green cotton panties. I could feel my cock pulse and push more precum into my boxers, but that would have to wait. I slid my knees back and got between her legs, the teasing long past now. She moaned softly in anticipation a I peeled the wet patch away from her lips and started swirling my tongue around, tasting her sweet juices. I spread her lips apart with my thumbs and lightly massaged her clit with my fingertips, and slid my tongue as far into her as I could. I replaced my fingers with my tongue and it was only a moment or so before she started bucking her hips into my face and cumming, squeezing my head with her thighs, but instead of letting her recover like usual, I doubled down, curled two fingers inside her and rubbed her g spot while I kept tongue flicking her clit. She thrashed around as I kept after it, cumming again, and soaking my knuckles.
I gave her a slight break while I kissed her- that was always a great feeling, kissing her after she came on my face- and she said something like “you really do like that, don’t you?” I told her I can’t get enough, and I went back down on her, moving her into every position possible to eat her out. For the next four hours, I ate her pussy so thoroughly- on all fours, laying prone, on her back, sitting on the bed while I was on my knees, sitting on my face, laying on her side. At various times I had almost every finger inside her, and the room smelled heavenly.
I leaked so much precum that it looked like I pissed myself. “If you promise to be careful, you can fuck me,” she told me. The bedside clock said it was after four. “Please don’t cum in me.” I was so turned on as she unbuttoned my jeans. I stood up and slid them and my soaking wet boxers off and knelt back between her legs. In the soft light, I could see how swollen and wet she was, and she reached down and swirled a large drop of precum around my head.
I knew I couldn’t last, and there was no way I could restrain myself after that. Bobbi slowly started stroking me with one hand while caressing her breast with her other, never breaking eye contact. I moved forward slightly and began sliding my shaft between her lips- we were both wet and slick, and even that slight contact had me on the edge.
“Bobbi…” I breathlessly began, “I’m gonna…” I couldn’t even speak. Bobbi lifted her hips and slid her lips up and down my shaft, essentially jerking me off with her pussy while holding my cock tightly against her. I started again, “Bobbi, I’m…”
“Cum for me,” she said in almost a whisper, knowing I couldn’t hold back. With my shaft between her swollen lips and the tip perched just above her trimmed bush, my entire body tightened and I came harder than I ever had in my life. The first two streams literally shot over her head and hit the headboard with a noticeable sound, and then I proceeded to cover her stomach, chest, neck, and bush in cum, the whole time she slid her hips back and forth, stroking me with her body.
Here I am, more than 25 years later, and I still think about that night. The relationship didn’t last, but it did leave me with two things: my wet panty kink, and a voracious appetite for pussy.