Some of y’all followed along with the [stories of Mary](https://www.reddit.com/r/gonewildstories/comments/ipatp1/freak_show_marys_final_act_blowjob_carnival/) (18), a girl from ages ago in my (20) life who gave me an incredible birthday present. In the [Pie-in-the-Face story](https://www.reddit.com/r/gonewildstories/comments/ig6kip/marys_week_of_cumswallowing_2_blowjob_carnival/) from this, I alluded to Mary’s friend Jessica (19) who pointed out that I had left some cum on Mary’s neck and that she probably guessed it because, well, I had cum on Jess at one point, too. So I thought I’d share that story.
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Mary and Jess were BFFs and had been for years since they grew up together. While Mary was Miss Popular, Jess was the quiet, studious type. She was obsessed with Jane Austen and fancied her boyfriend a Mr. Darcy. She was a musician, playing some sort of string instrument. I was a kinda chubby, brainy nerd, eventual honors grad who yet somehow managed to be reasonably popular and well-liked. Frankly, Jess and I were fast friends, even having our own two-person book club at one point.
Let me take a moment here to describe Jess. Jess is absolutely gorgeous, but not in a conventional way. Jess was a full-bodied woman through and through. She was by no means skinny, had big hips, big DDD breasts and a full waist, but she carried it effortlessly, like she was walking on air. She stooed 5’3,” almost a few 7 inches shorter than me. Her face had a square shape with her forehead, cheekbones and jawline almost all the same width and a sharp chin, but all softened by her body, giving her cheeks that were naturally blushed, deep cheek dimples which always showed and softening the kindest hazel eyes that, by 19, already had early crows feet wrinkles because she was never NOT smiling. She had the most perfect retrousse nose with soft rounded tip, (imagine Little Caprice in a fuller bodied woman). She had soft, but kind of thin lips and a nice wide smile that showed off her upper teeth which were an almost perfect set of large pearly whites. Her skin was a soft white with the lightest brown freckles you can imagine scattered all over. This beautiful face was capped by the most luscious flowing locks of red hair you can imagine. Jess even had the soft lilting voice that made her the southern belle of any boy’s dreams – a true girl next door. And lucky me. She basically lived next door.
I didn’t actually catch on that Jess was attracted to me until she actually asked me out to a dance. But I was too nervous to ever do anything more than kiss occasionally when I first knew her. But she gave the warmest hugs and made you feel like in that moment, you were the person she cared about most in the world. And it was probably true – she was an amazingly thoughtful and considerate friend, too.
Jess and I had probably “dated” for 2 years by that point but the most we had ever done was cuddle and spoon clothed, watch movies, play the occasional grab ass and, when things got *really* hot and heavy, kiss.
Jess had a big plush chaise that fit us both and was our favorite spot to cuddle for a movie with a fuzzy blanket. I honestly don’t remember what we were watching one day but I remember it was winter and we were under the blanket. It was some movie that had a scene where a couple was having spooning sex under the covers and their hands were all over each other. At one point we were in the same position as the actors were and the woman runs her hands up the man’s thighs and over his butt to pull him inside her. I don’t even think she realized it but she mimicked the movement and ran her hand absentmindedly over my butt. I had kept my distance because I was already a mile ahead of her in my fantasy and had a hard on. When she pulled my hips close, my cock pressed into the back of her jeans, startling her. She giggled in only a way she could that completely disarmed me and snuggled closer. She took my hand and placed it under her shirt on her abdomen and turned her head to face the ceiling, looking over her shoulder best as she could and said softly, “I think you should kiss me.” I propped myself up a little so I could move my head over hers and softly kissed her. I enjoyed the feel of her lips, soft skin and flowing curves. I ran my hands over her hips and then back up underneath her shirt and over her abdomen. “Mmmm… more please,” she cooed as our lips separated. I kissed her again and felt her hand over mine, guiding my hand up. My cock twitched as my hand touched the underwire for the first time and she smiled, giggled again but never opened her eyes or stopped kissing me back. As she escorted my hands over her breasts, I could feel the soft fullness of her large breasts beneath the unpadded bra. Her hand left mine and I made to move my hand away, too, but she stopped my hand, returning it and saying, “No, go ahead, you can explore today, I like it.”
And explore I did. Tracing my fingertips up and down the deep valley and around her globes, finally sliding underneath the fabric and exploring her areolas and nipples for the first time. Her breath got heavier and she was pushing in closer to me as she involuntarily ground her hips side to side against my erection. Her breasts were exquisitely sensitive and she was very clearly being turned on.
I had no idea how sensitive until I felt her shudder and she suddenly shot up and ran off hastily saying, “Oh, gotta go to the bathroom!” She was gone a solid 5 minutes.
When she came back, she had changed into leggings and a big tshirt. She cuddled back up underneath the covers with me. I wrapped my arm around her thinking that fun was over and we were going back to the movie. But she pulled my hand back underneath her shirt. As I boldly slid my hand back up her body, I immediately returned erect as I discovered she had no bra on. “I thought you might like that” she whispered coyly, playfully wiggling her butt against my dick.
Once I had played with her breasts some more, I decided I’d try to be bold. I ran my hands down her belly and slipped a finger under her waistband by her hip. She quickly pulled it away and returned it to her breast, setting a firm boundary. In fact, that was a boundary she and I never crossed. As I squeezed, kneaded and teased her breasts she began to breathe heavily again.
“We’re not really watching the movie, are we?” I asked.
“No, I guess not,” she replied and turned around to face me. We kissed and let our hands wander, mine over her chest and hers over the bulge in my pants. My roving hands had lifted her shirt up over her chest and as it was bunched under her arms I think it got uncomfortable because she sat up and in one swift motion, took her shirt off, her giant DDDs swinging into view. She had small areolas, very light pink, and capped by hard perfectly round big nipples. I sat up as well before she could change her mind and kissed her passionately never stopping the heavy petting which was so clearly turning her on. She now had her hand trying to make its way inside my waistband and I obliged her by loosening them on the sweatpants I had on. As we were sitting facing each other, it was still awkward for her to get her hand inside and I instead just stood to take them off, my erect cock in my underwear now showing. I sat back down again and kissed her again on the lips and then on the neck, nibbling her ear lobe and breathing into her ear. That must have amped her up because her hand found its way into the fly on my underwear. She sighed as her hand made contact with my shaft for the first time. She held it with a reverse grip and slowly and awkwardly stroked it, eventually freeing the shaft through the fly. By then I had worked my way down to her chest and for the first time got to taste the flesh of her breasts. I kissed my way into the valley between her hanging globes and relished the softness against my face. Her work with her hands gained new urgency as I took her nipple into my mouth for the first time, holding the weight of her breast with both hands. I played with the nipple with my tongue and then switched to the other.
I knew I was getting close but we had never been anywhere in this territory together and so I warned her, “hey, um, I’m kind of close to, you know, so if you don’t want…” I trailed off. She caught me off guard, “Can I watch?” “Um, yeah, I guess, I said awkwardly.” Not knowing what to do in that instant, I stood up again, cock through underwear fly standing erect, now pointing directly at her breasts, nipples gleaming with my saliva. She scooted closer and looked up at me, “Do you, you know, jerk off a lot?” “I’m a dude, so yeah,” I replied trying to play it cool that I had my cock out in front of a topless Jess. “Can you show me how you do it?” She asked. I took my shaft in my left hand as usual and began to stroke it. “Ooooh, wow,” she said to no one in particular and scooted even closer.
Instinctively seeing her face approaching, I changed the angle of the tip toward her smiling lips. Her smile disappeared, “No,” she set the boundary clearly, taking the shaft into her hand and pointing it away from her face and taking over stroking the shaft. I reached down with both hands now free, cupping both her breasts and pushing them together. In doing so, my hips pushed further back and away which she didn’t like and she pulled firmly on my cock. Almost losing my balance for a second, I stood upright and stumbled forward a step, my cock hitting her upper chest. A drop of precum pulled away attaching our bodies and broke, falling onto the mound of her left breast. “Is there more of that?” she asked coyly, keeping up the pace.
“Yeah,” I said, now my turn to be panting and breathless. And then the swell. “Ok, I’m cumming,” I stammered. She let go and sat back suddenly, leaning back on her hands to watch. The first contraction angled my cock up and shot a spurt of cum arcing into the air. Before she could move it had landed midway up the bridge of her perfect retrousse nose, crossing from cheek to cheek, the whiteness of my cum highlighting the deep blush her cheeks had taken on by her heat. As she squealed, I grabbed my cock and the subsequent shots landed on her chest and magnificent breasts and the last hit on her waistband.
“Oh my gosh,” she yelped and pulled away her sweatpant elastic strap from her to keep the cum off her. As she stood up to run to elsewhere, I caught a glimpse of matching fiery red pubic hairs. About 10 minutes later she had come back. I had dressed again, frankly, in case she threw me out for cumming on her.
About 10 minutes later she came back out. Dressed again and wearing a bra. “So, um, that happened,” she said. “Yeah, it did. Are you okay?” I asked. “Yeah, um, I think so. But maybe let’s call it a day, ok?” I understood where she was coming from. For a couple that had barely gotten down kissing, I had just accidentally cum on her face after a heavy petting session. “Yeah, okay, no problem,” I said, wondering if there really was a problem. I headed to the door and started to walk out. She grabbed me by the hand as I passed through the threshold.
“Hey,” she said, and I turned around. I was greeted again by her usual gorgeous smile, She hugged me and looked up into my eyes and planted kiss on my lips that lingered for a full second. “See you later, stud” she said playfully as she winked at me.
Jess and I never went beyond that, though, and I wonder if she ever told Mary.
Source: reddit.com/r/gonewildstories/comments/isgw0t/cumming_on_marys_bffs_ddds_mf
This should be entered in this month’s contest