A Series of Exploration Part 1: The Ex and her friend. [mff]

I intend on writing different parts to this story, each describing an encounter that changed my life.
I’m at a point in my life where I’m more confused than ever. This last year has left me wishing I had a clear answer for what I wanted, what my morals and values are, and what I deserve for my actions. Maybe recounting these critical moments in my life will help, maybe your comments will guide my emotions.

I’m a slow burn kind of guy. Just a warning that these will be long, with more build up than most stories I’ve read on here.

This is the story of my Ex, her friend, and a college dorm.

But first, some backstory

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Jess and I had met while volunteering at an afterschool day care. I was the excited 8th grader, and she was the innocent 6th grader. We became fast friends and the kids would tease that we’d be together forever and ever.

We took turns admitting to each other our feelings, and subsequently took turns denying the feelings and using the age difference to justify avoiding each other. I was heading to high school, much to old to be dating someone in middle school, right?

Fast forward two years of boring high school romances. I had kissed exactly one girl, and it was thanks to my sadist brother making her “pay” for a bowl to smoke. Starting my junior year I find myself in charge of freshman orientation, and lo and behold Jess was assigned to my group.

Jess showed signs of maturing; her colorful tank tops showed her use of a bra to hide tiny breasts, her hips had widened slightly and she had finally started styling her hair. The chemistry we had years early immediately flared up, and we spent the entire tour giggling as we caught each other staring.

She was my everything. I would skip tennis practice to hang out with her. I came in early (my first block was off) just to wait at her locker and tell her good morning. Everyone assumed we were a couple, so at some point we decided to make it official.

Jess and I shared every first imaginable. First consensual kiss, first groping through clothing. Our passion burned hot and raw, blossoming quickly. Three months in I had taken her virginity. We were like rabbits, constantly hiding our antics. Under the school stage, on the football field at night, nowhere was safe from our horny teen eyes.

I never did well in school; a combination of ADD and a mother that would constantly tell me that without medication I was nothing took away all drive I had for succeeding. My ACT scores carried me though and I was accepted to my first choice college without having to write an essay.

I was an education major which meant I was placed in the education dorms. My entire floor was full of freshman girls, all swooning over my roommate and me. There were attempts to seduce me, offers of discreet sleepovers, and innocent back rubs that had to be cut short.

But I loved Jess. Nothing could change that, so I pushed it away.

College was awful for me. I couldn’t put myself through the troubles of homework and just fell into a depressed pit of drinking and smoking weed. By the end of my first semester my father informed me that I would be on my own in terms of paying for college.

I spent the next semester and summer after working two jobs and saving up in order to return for the fall semester, but that never happened. I was with Jess every chance that I could get. I bought her everything. I wanted her to see me as someone worth staying with.

My dad had a long conversation with me in June of that year. My step mother had convinced him that I was to be given an ultimatum; go back to school in the fall, or find a place of my own. Enraged, terrified, and horrifically sad I left the house and stayed with a friend for a few days. I wasn’t ready to be on my own. My brother had moved out at 17, and was seemingly stuck living paycheck to paycheck working at a sandwich joint. I hated him, and wanted to be better. I wanted to be worth something.

A week later I walked into a recruiting office for the Navy. A day after that, I took the entry test and scored incredibly high. I took whatever job sounded the most impressive, working as a sonar tech on a submarine.

I never discussed enlisting with Jess until after I had learned I would be heading to boot camp that August. She was devastated, screaming and crying at me. I was devastated. After some time we talked and decided it was a good idea. 5 years in the Navy would get me free college and let me mature enough to take it seriously.

Bootcamp was difficult but I found myself enjoying the experience overall. Every day I would write Jess pages of letters. Every day the drill instructors would laugh and make fun of me as I tried to fit them in envelopes. I would wake up at 2am on the weekends to steal the office phone and leave Jess 30 second voicemails spewing my love in hushed tones.

After bootcamp I was sent to my rating school to learn about submarines, electronic circuits and sonar. I was fascinated by it all and excelled there. It also had the perk of being in Conencticut, where I was raised in my first few years.

Throughout my relationship with Jess, she had a group of girlfriends who in my opinion were all awful people. They used Jess constantly and manipulated her emotions. They were horrific prudes so against sex they were against us entirely. Jess made me lie about our lustful ways, and only admitted to letting me finger her 2 years into the relationship. But there was one friend, a late comer to the party always on the sidelines. She was nice, and curious about everything. She had grown up in Russia with Catholic parents, so she was a blank canvas when it came time for her to go to college. Her name for the purposes of this story was Ella.

Now for the meat of the story.
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I flew back home to visit Jess. She was living in the dorms and in the middle of her first semester at college, studying things I wouldn’t dream of understanding.

We stayed in her dorm, squeezing together on her twin loft mattress and huddling close for warmth. Her roommate slept across the room from us in her own loft bed, nothing dividing the room.

Jess had thought ahead and when it time for her group of friends to pick roommates, she chose Ella as she was the only one who didn’t view me as an evil corruption.

Jess was beautiful; google the supermodel “Twiggy” for an almost carbon copy of her. Incredibly skinny, 5’8″ 120lbs, size “B” breasts. Her body had always been my obsession; in the rare cases that I would watch porn it was always with actresses that modeled Jess’ body.

Ella was a different story. Classically beautiful, full breasts and around 5’6″. Long black hair fell neatly behind her shoulders, and her skin was paper white.

Ella’s eyes had always captivated me. They were piercingly blue with streaks of silver, large orbs of innocent emotion.

It was late. The room was pitch dark save for the soft blue glow of christmas lights under the girl’s loft beds. Ella was fast asleep turned away from us on the far side of the room, and it had been a couple of days since Jess and I had made love. I spooned her and let her feel my growing cock press against her ass. Jess turned and kissed my cheek softly, holding a finger to her lips and smiling.

Her legs spread and her hand guided my member between her firm thighs. She squeezed and moved her legs, causing me to twitch in anticipation. I could feel her warmth inches away from the head; I needed her.

I slowly found the bottom of her shirt and peeled it upwards. Jess lightly protested, holding my hands for a second as she stared at Ella. I nibbled on her neck and she finally gave in, allowing me to lift her shirt and reveal her perfect breast. She looked breathtaking in the pale blue glow, her curves highlighted like an artsy movie scene. The cold winter air made her nipples immediately firm up as I watched goosebumps slowly form all over her upper body. I took her breasts in my hands, firmly grasping them as I started to slowly thrust my hips and rub her panties with my throbbing shaft.

Jess bit her lip and breathed heavily as her hand slowly reached down and pulled her panties out of the way. As I placed myself at her entrance I watched her stare across the room and cover her mouth.

Even through her hand I could hear the moans as I slowly entered her. I felt her warmth surround me, her juices covering my balls as I bottomed out inside of her. The bed made a quiet squeak with every shift of my hips, so I slowly moved in and out of her letting her feel my every inch. Her eyes were shut tight and hand pressed firmly over her mouth, her breaths hot and heavy through her nose. I closed my eyes and pulled the blanket up to our shoulders as I slowly increased my pace. My hand left her breast and moved to her neck, her veins bulging against the pressure.

“Are you guys….having sex?” A whisper from across the room. I immediately stopped moving, my cock twitching deep inside Jess. Ella sat up in her bed across from us, the covers pulled up to her shoulders and legs crossed. Even in the dark light her eyes seemed to glow.

Silence, neither party wanting to respond. I pushed my hips slightly, causing Jess to push on my waist in a futile effort to stop my movements. I stared into Ella’s eyes, waiting for Jess to respond.

As my eyes adjusted I noticed a movement under Ella’s covers. I matched the rhythm with my hips as Jess’ nails dug into my skin. Jess was soaking wet as she stared into her friends eyes. I slowly pulled our covers down, revealing my girlfriends tits to Ella. Ella bit her lip and looked away, the movement between her legs ceasing. Slowly her covers fell, revealing her lace bra and tight stomach. In the light I could barely make out the waistband of her matching panties.

Jess let out a moan as we threw inhibitions to the side. The bed creaked away as I thrust into her, and Ella resumed her self pleasuring. The motion of her hand rubbing pushed the covers out of the way and I could see the sheen of moisture on the crotch of her panties.

“Kiss her…” Ella whispered. I put my hand on Jess’ jaw and turned her face to my own, my tongue pushing between her teeth. Ella moaned and picked up her pacing.

I suddenly stopped and whispered into Jess’ ear. She looked back and thought for a moment, then slowly nodded her head. I pulled out slowly and crawled over her. I climbed down the ladder and lay on the ground, my glistening cock standing straight up. As Jess crawled down to meet me she giggled at Ella.

“Why don’t you get a better view?”

Jess straddled my hips and smiled as she pushed me deep inside. I moaned and closed my eyes. Taking the cue, Jess grabbed a shirt from the floor and placed it over my face. She rode me, hands placed firmly on my chest. The carpet rubbing on my shoulder blades hurt but I didn’t care.

I heard feet against metal rungs and had to grab Jess or risk immediately exploding deep inside of her.

I desperately wanted to remove the shirt. I needed to see.

Lips kissed me. Familiar, they must have been Jess’. Hands brushed across my chest. Short fingers. Not Jess. A finger circled around my nipple causing it to harden, then traced down towards my waist. Just below my belly button it lifted off, then Jess moaned loudly. Movement between her legs suggested she had started stimulating her clit.

Jess placing her hands on my chest suggested it wasn’t her doing the stimulating.

Shifting bodies. I felt Ella’s hair brush across my shoulder then heard lips hungrily meeting each other inches from my covered eyes. I reached up and slowly pulled the shirt down to watch Jess slide her tongue in and out of Ella’s mouth. I reached up and pinched Jess’ nipple. She broke the kiss and looked at me, momentarily lost with a glossy look in her eyes. She grabbed my hand then slowly guided it towards Ella.

Ella melted as my hand felt her impossibly soft breast. It filled my hand, spilling slightly over the side. The nipple poked into my palm and Ella gasped, her breaths short.

Jess kissed me and starting riding me hard. I felt Ella move and straddle my legs below my knees, her tight ass resting against my feet. I could feel her arms against my hips, behind Jess. One of her hands lifted and I watched as she slowly reached behind Jess and out of view. Jess leaned forward, pressing her chest against mine.

Dainty fingers traced my thighs upwards, the hairs standing up and goosebumps forming. Ella smiled at me and kissed Jess’ back as her hand slowly landed on my balls, rubbing them and causing me to cry out in pleasure. Jess road harder and harder, and Ella’s eyes widened as she watched my balls tighten and pull against my body, my cock swell inside Jess and my legs spasm as my orgasm ripped across my body.

Jess slowly rose off of me and stood up, Ella still straddling my legs. My cock throbbed, pushing out small drops of cum. Ella was mesmerized.

Jess moved to straddle my face, hovering just above me and letting my own seed drip out of her and onto my waiting tongue.

“Can…I?” Ella whispered.

I kissed Jess on her swollen lips and easily pushed her off of me and onto her back. I straddled Jess around her stomach and leaned back to hold her arms out to fight her protests. Jess giggled as Ella crawled between her legs, mesmerized by the visage of thick white cum slowly dribbling out of her glistening pussy. Ella lowered her head and I collected her hair in a ponytail. I pushed her face into Jess’ crotch and both girls simultaneously moaned. My cock had rested and was rising for a second round.

Jess twisted her body below me in waves of pleasure as Ella explored her with her tongue. I let go of an arm and reached around to slowly stroke my throbbing cock. Ella looked up and I saw her eyes follow the movement of my hand. She looked hungry.

Ella kissed her way past Jess’ swollen clit, past her neatly trimmed landing strip and stopped, her mouth inches from my shining tip.

I turned to Jess and gave her a questioning look. I could feel Ella’s warm breath on the head of my cock. Jess pondered for a moment, then used her hands to push my hips forward.

Ella started with kisses around the length of my shaft, exploring me with her mouth. As she took me inside, I could tell she was inexperienced as the feeling of teeth dragging along my length. She couldn’t fit much more than 3 inches in, and I sat still to avoid complicating things. It wasn’t great, but was the single hottest thing I had experienced at the time and I could feel myself getting close again. I lightly pulled her off of me and stood up.

I started stroking my cock, and Jess got up on her knees, motioning for Ella to join her. They held each other close and kissed deeply. I started to breath heavily and moan at the sight. I could feel my legs getting weak and started losing myself. I looked down and saw Jess holding Ella directly in front of my cock, her fingers prying Ella’s mouth open and Ella’s tongue sticking out. I came instantly, hitting her nose and teeth. I collapsed to the ground and we all cuddled, naked, panting, and sweating.

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It was supposed to be the start of something beautiful. A sexual awakening for everyone. The next morning we had chatted about boundaries. Ella informed us she was a virgin. Jess didn’t want me to take it.

I had never seen Jess more turned on than those shared moments and it had awakened something inside of her. She liked being watched, and liked having the opportunity to explore women.

The problem started later on, after I had left and expressed an interest in experimenting with men.

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Thanks for reading. This is my first time writing, so feel free to give me tips. I had to change parts to avoid identifying moments in the night.

Before anyone asks, Ella ended up turning into a bad person and was effectively ejected from the group. Jess and I never added another to our bed after that singular experience. Jess continued to play with girls while I was gone, which I was ok with. I let slip at one point that I wanted to experience being with a man, and our relationship slowly fell apart.

Jess won’t be in another story. After 7 years we broke up. I ended up loving the Navy as a career and reenlisted. Jess ruined me emotionally in the breakup. Telling me I didn’t satisfy her. That I wasn’t attractive to her anymore. That we were taking a break and she was staying with her best friend Ryan.

She broke up with me when I was hundreds of feet underwater, unable to reply.

That was the start of this confusing year.

Take care everyone.

Source: reddit.com/r/gonewildstories/comments/cak64a/a_series_of_exploration_part_1_the_ex_and_her