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[MF] I kept a journal | 2016

Hey GWS! I've lurked and enjoyed this sub for long enough. Might as well contribute. Forgive me in advance, I'm on mobile and will format/spell the best I can.

I often reflect on past encounters and while I have kept a journal of some steamy experiences, it certainly has it's gaps. My goal is to eventually share at least the first time with a new partner. For better or worse, the first meet has always been the most memorable and vivid to recount. I might spur off with later highlights but the focus of each story will be first time with someone new. Names will be changed but the rest is the real deal.

Losing my virginity is as good a place as any to start, I suppose. Growing up we had a close family friend with a daughter that used to babysit my younger cousins. She was 5 years older than me and we never really hung out til I was a junior in highschool.

"Jill" was 22, had her own apartment and was in college. She and her friends were definitely more my crowd when I was in highschool. She'd frequently hit me up to be the DD for she and her girls when they'd hit the club's downtown. To be honest, I never had a strong sexual attraction to her. Not that she wasn't attractive, just growing up with someone can put a damper on desire. If I'm honest, I was really after her slutty friend. The one that was always in the car on the way to the club but never for the ride home.

One night, Jill invited me over. She knew I worked close to her place on Saturday mornings and would let me crash there when I wanted to be outta my parents house. I fully expected to be carting the group downtown but there were only 2 others and everyone wanted to stay in. Card games, music and drinking; everybody was taking it easy.

I had a few beers and was starting to nod off. Jill said I could pass out in her room since it's quiet and I'm working in the morning. I made my way in, got partially undressed and flopped onto the bed. I was half asleep when I heard people filtering out the front door. A few minutes later, Jill opened the door.

"Quit jackin' off in here!", she said loudly. "Hand check!"

I scoffed, laughed and covered my face with a pillow to block the light. Jill was always overtly sexual and very vocal about it but never really backed it up with any action. She crawled in to bed before I could peek at what she was wearing. She laid on her side and and before I knew it, she had inched her way over to me.

"Wanna cuddle?", she asked playfully.

"Sure?!"

I was a little caught off guard but my teenage hormones were already figuring things out. I rolled on to my side and wrapped my arm around her. She pressed back against me, wiggling her ass a bit as she settled in. My cock was instantly throbbing through my boxers, nestled between her cheeks. There was a pause. Maybe only seconds but it felt like an eternity.

"Hmmmm... somebody's horny..."

"What do you expect from me? Hahah. I'll roll over if it's bothering you."

"No. I like it." She pushed her hips back firmly.

"How far have you gone with a girl? Did you have sex with your ex?"

"No. I don't know why though. Just never happened."

"Are you saving yourself or holding back for some reason?"

"Not at all, just hasn't happened."

She reached back and began exploring for my cock. She tugged at the waistband of my boxers and I was happy to slip them off. Her hand ran up and down my thigh as she started to grind on me.

"This ok?" I felt her hand around my dick. She squeezed me while gently stroking the shaft.

"Mmmm... absolutely." My hand now cupping her breast, I began tugging at her nipple.

"Good. I don't want to take anything that you aren't ready to give up."

The suprise followed by the immedate feeling of anticipation is something I'll never forget. She started to firm up her grip and tug at me, rubbing my head against the back of her lace thong.

My hand wandered from her breasts. Pressing it against the front of her thong, I could feel the heat radiating from her crotch. She grinded against me, harder now and let out a soft moan as my fingers found a way into her panties.

I could feel them peel off her skin, sticky and wet. I slowly worked her clit. Grinding harder now, I slipped a finger in and out in rhythm.

"You're so fucking wet.", I whispered before sucking on her ear.

"I'm not the only one... your precum is smeared all over my ass!"

Less than a minute later, she finally asked,

"Want to put it in? I want you to..."

I hesitated, paranoid from highschool health classes and MTV 16 and pregnant,

"Condom?"

"I don't have one. I'm on the pill. Just pull out and we'll be fine."

Before I could say anything, she had guided my head to her waiting lips. Slowly but firmly, she pressed against me, this time easing my virgin cock inside her. I slowly started pumping, deeper and deeper with each stroke.

Her hand now grabbing at my ass, pulling me in harder. As you may expect, it was short lived. Hahah. And far from a memorable finish. I pulled out before I came. I covered her ass and thighs with my cum. We finished as suddenly as we had started.

She never got up to clean off. We passed out together and didn't mention a thing in the morning.

Jill and I continued to hook up for a while. Even after she got pregnant and broke up with the father before the kiddo was born. But that's another story for another time.

Thanks for reading. Looking forward to posting more exciting stories but had to start somewhere.

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