Heather and I had only been dating a short time leading up to her ummmm... enjoyable experience horse riding at my parents place which I wrote about previously. If you haven't read the story, its essentially a recounting of how Heather had an orgasm while in the saddle. It's pretty common. Just ask any woman with a horse or... a Harley Davidson for that matter.
In fact, my wife, who by the way helped with the embellishments in this story, too would experience this phenomenon some years later.
Thanks for your contributions, April. (The Wife)
For context, Heather was my first real girlfriend after losing my virginity and the other experiences with my cousin, Melanie which I have also previously written about.
Heather was a little different than all the other girls I knew when I was a teenager. She was cute and funny and a little bit of a "tomboy". I'm sure it's because she had two older brothers that were both in there early 20's by the time we started dating. Even though she was 16, she had a flat chest and small flat ass. I still liked to look at her when she wore a bikini or bluejeans. She was a little behind in physical development next to other girls but she had a great self-deprecating humor about it. "Goddamn, I wish I had tits like her!" as we would walk past a well endowed woman at the mall.
"Meh... I'm an ass-man." Was my usual response. Which is true.
As part of her tomboy-ish personality, Heather would just say what was on her mind. She would make funny remarks about her body, my body, the way she smelled or the fact that she hadn't showered in a couple of days or when she was feeling aroused!
"That makes my vajayjay tingle!" She remarked during a lovemaking scene in a movie.
Up to the point when she had her horse riding "experience" at my parents place, we hadn't really done much sexually. We had made out and groped each other through our clothes but that was pretty much it.
While my parents had a pretty strict leash on me Heather's parents were very different. They were really just kinda indifferent to whatever it was we were up to whereas my parents wanted to know every detail about where we were and what time we would be home. If we were hanging out at my house, my mom watched us like a hawk! Like somehow we were gonna drop our clothes and start fucking if she dared leave us unsupervised for more than 5 minutes. It was a little absurd at times.
A few days following her first horse ride, Heather invited me into her place after school. Her mom greeted us as we walked into the house and offered us something to drink as we sat on the couch in front of the TV then grabbed her purse and jacket and headed out the door to run some errands. As the front door closed behind her mom, Heather stood up and said that she had to pee and would be right back. When she returned she had changed out of her school clothes and plopped down almost in my lap wearing gym shorts and a t-shirt. She wrapped her arms around me, planted her lips to mine and aggressively forced her tongue in my mouth. As I embraced her I felt the absence of her bra and she paused for a moment, looked at me with a smile and lifted her shirt over her breasts and head and discarded it into the floor. Her tiny nipples stood at attention as I nibbled on them. Heather's hands found the buttons of my pants and released them to gain access to my erection.
"Holy shit, you're hard already?? That didn't take much!" She giggled as her hand disappeared into the front of my pants and grasped my penis in her small hand but struggled to stroke it within the confines of my underwear and jeans.
"Hold on..." Heather stood, pulled and slid my jeans and underwear to my knees.
"Oh my God! You have foreskin?!?"
Heather's eyes widened and her face was aglow with a smile that went ear to ear.
Ah jeez... I don't think my face had ever been that red!
Heather was the first girl I had been with since my cousin. My first real girlfriend. Mel had never really said anything about the fact that I wasn't circumcised. I felt a little self conscious.
"Sorry... there's nothing wrong with it. I wasn't expecting it. I've never seen a guy that had foreskin."
Wait a second... how many other guys has she seen?? I wondered.
Heather bit her bottom lip as she gently pinched the end of my foreskin between her thumb and forefinger and rolled it around. Her eyes examined the details of my penis as she inquisitively ran the tip of her fingers along the veins down to my balls and teased my hairs. Heather started to stroke my penis in long strokes, running the palm of her hand the full length of my erection. With each slow stroke she would slide my foreskin back revealing the tip until she rolled it back completely revealing the engorged head of my penis.
"Oh, there you are!"
I laughed at the tone of her voice. It sounded like she had just found a lost puppy! I slid my hand over to the crotch of her gym shorts and slipped my hand between the fabric and her thigh of one of the loose leg holes where my fingers met a mound full of hair. No panties.
My fingers fumbled through the hair and wetness searching for her clit and vaginal opening of which my index finger found. Heather moaned as i slipped a finger inside of her and made circles around her clit with my thumb. After several minutes of trasing her clit and dipping my finger into her, Heather released her grip on my cock and grabbed my arm with both hands. Her hips began to buck with every thumb-roll of her clit and the introduction of a second finger now penetrating and gently stretching her. She gasped for air...
"Just like that... don't stop... just like that." Heather's voice was weak and broken as if trying to catch her breath. Her body tensed and legs clamped down on my hand as she let out a loud moan followed with a cry as she orgasmed and collapsed into the couch. Breathing heavily she opened her eyes and stared up at me. I withdrew my fingers from her vagina and now soaked gym shorts, brought them up to my mouth and sucked on them. Heather smiled as her hand returned to my now aching penis and feverishly began to stroke...
"This angle just isn't going to work," she said as she re-adjusted herself from the couch to the floor between my legs and began to quicken the pace of her strokes! As her grip slipped along my shaft her other hand cupped my scrotum and then opened her mouth and enveloped the fullness of the head in her mouth. With every stroke and suckle of my cock, the intensity swelled and begged for released. Heather released me from her mouth..."Don't cum in my mouth, okay?"
Unable to talk, all I could do is nod. Heather switched hands and jerked harder. I could tell her arm was getting tired.
"Okay... okay!" I warned Heather of the immediate impending climax just mere moments before the orgasm hit like a freight train and cum exploded from the end of my erection shooting onto the couch, Heather's chin and naked chest.
It was a complete mess! Heather stared into my eyes and smiled as she held the end of her tongue between her teeth.
"Ummmm.... I think we need a towel."
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