[M]y [F]irst Time [Cheating] With Lily

If you want to skip to the action, go to the *****

My name’s David, and this story takes place nearly a decade ago when I was 21. For a brief period of time I was sleeping with my OG high school crush, Lily. Lily and I had always been close friends in high school, but owing to my own nerdy demeanor and bad timing with our other relationships we had never actually gotten together during our teens. Like a lot of guys, I didn’t find my confidence until University, when girls started noticing and hitting on me for the first time.

Lily was an absolutely bombshell. 5′ 9″ (somewhat shorter than my 5′ 11″) with alabaster skin in contrast to her crimson red hair and sharp green eyes. Her classic hourglass frame and plush D breasts made her the subject of many people’s attention – guys and girls alike. She was the most outgoing bisexual girl I ever had the pleasure of seeing romantically, and was simultaneously flirty but dismissive in a way that just made everyone around her crave more of her attention.

I was no different, and was head over heels for her for years before we got together. After all, she was witty and sultry – even before you considered how physically attractive, she was. We had suffered from bad timing in the years we knew each other. In the years we were actively dating, it was often the case that either I was with someone or she was with someone. The first time we actually fooled around was at age 21 when we were helping a mutual best-friend move. This is that story.

Our friend Andy had taken a job in a smaller town three or four hours outside of the city, and needed people to help transport furniture and boxes upon boxes of his stuff. I had a car, and while it wasn’t big, I was always happy to help Andy as he had been my best friend for years. We packed up his PT Cruiser and a small tow-along trailer and filled my sedan to the max. Lily road shotgun with me, and got comfy right away controlling the tunes as we pulled out of Andy’s parents’ driveway.

One thing burned into my memory forever is Lily’s scent. She had this wonderful aroma – it was like a strong fruity cream soda that made me lose myself anytime she was close. I think she’s the reason I found myself attracted to women with unique perfumes/aromas as I grew older, and being trapped in a car for a few hours of travel made the pull of her scent unavoidable.

I should point out that at this time in my life… I was seeing someone else. It wasn’t overly serious, but at age 21 I was a good boyfriend – and had no intention of violating my girlfriends trust. Lily however often made me lose my senses, and this trip was going to prove to be one of those times.

We had a good time of the trip, laughing and talking to while away the time. At one point the conversation pivoted to sex, with Lily asking about my current girlfriend. There weren’t many off-limits topics between the two of us, and so she knew that a few months earlier my girlfriend had gone on the pill – so that we could enjoy each other bare. Lily asked how much I’d loved the change, remarking “I can’t get guys putting up with girls who won’t let them go bare. I can’t imagine missing out on that”. I chuckled nervously (shifting slightly to compensate for the instant hardon her remarks gave me)- not wanting to dive into a potentially dangerous area of conversation. It was probably in my head, but I felt like her aroma became stronger at that moment.

When we got to Andy’s new apartment, the three of us unloaded his belongings as efficiently as we could – at one point taking advantage of a window in a somewhat irresponsible way. It was almost dinner time when we finished bringing up the last of his boxes. I had expected that we’d be heading back soon after – but Lily had different expectations, saying we should get some dinner. We picked up some McDonalds (none of us knew how to cook very well at this age) and ate it on Andy’s sparse furniture. His little studio apartment was populated by a pullout couch, a bed, a TV sitting on the floor, and a single chair.

After dinner, again I thought we’d be heading out – particularly because I worked first thing in the morning back home. But again, Lily had other ideas, and said she wanted to play a card game. I always had a tough time saying no to her, so we stuck around and played games for a few hours.

At around 10, I said that we really needed to go, I was getting tired. Both Andy and Lily argued that I shouldn’t drive tired, and said that we should just crash there that night. Andy’s bed was smallish, so somehow, we settled on Lily and I sharing the pullout couch, three feet from his bed.

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*****

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I hadn’t been prepared for an overnight trip. Otherwise I would have had a pair of PJ pants and a loose t-shirt for sleeping around other people, even though I typically slept in my boxers at home. Lily suggested we just strip down with the lights off – as she also didn’t have any guest-appropriate attire for sleeping.

At age 21, I wasn’t overly experienced, and the prospect of being mostly naked in bed with the redheaded bombshell who had occupied my dreams for years was very… distracting. I was harder than steel as I shimmied out of my jeans in the dark. I climbed under the covers and could sense her moving on the other side of the mattress. She clearly took off her jeans as well, and had snaked her bra out through her t-shirt. She laid on her side, facing away from me, and I stayed firmly planted on my side, assuming that the plan would be to stay apart to maintain some decorum. I was incorrect.

As the room settled, I starred at the ceiling, willing my erection to subside. Slowly it became more of a semi, as I thought that the night was over – but every once in a while, I would catch a waft of her aroma that would bring it back in full. After about 10 minutes, Lily shifted back towards me, until I could feel her leg grazing mine. She then leaned back, and touched by arm – beckoning me to cuddle her from behind. We had done that before – on school trips and on couches watching movies – but never with as little clothing as we had at the moment.

My better judgement being ignored, I complied. I curled up behind her, letting our legs touch more and my arm fall around her – but very cognizantly pulled my hips away to prevent her from feeling how wound up I had become. After a few minutes she shifted a little, cozying up more (I assumed to get comfortable to sleep) and still I tried to keep my distance. This left me in a very awkward pose, that ultimately was too difficult to maintain.

Once more she shifted around, and this time the tent in the front of my boxers unmistakably made contact with Lily’s tantalizing posterior. In that moment of contact, I was made painfully aware that I had been leaking precum from my hard cock. That sticky fluid had soaked through the boxers and had been what she would have first felt when I prodded her. That sticky hot precum poking into her perfect ass confirming without a doubt what she probably already suspected – that I had nothing but lewd thoughts filling my head at the moment.

Meanwhile, Andy was mere feet away – and I had no way of knowing if he was blissfully unaware having fallen asleep, or if he too was still awake.

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I pulled back sharply – and could feel the string of precum from what small deposit I had to have left behind on her ass. In that moment I wanted to die of embarrassment. But then… after a few seconds, she pushed her hips backwards, and pulled me around her tighter – bringing our bottoms into contact again.

In the future, I would look back on 21-year-old David with his naivety and laugh. I had thought that she was just gently letting me know that hard-ons are natural and that she took no offense to my forward manhood. I thought she just wanted to enjoy some cuddles and was trying to ensure that my erection wasn’t the reason that things became “awkward”. She was a very liberal and progressive person, so that would fit my view of her personality perfectly.

What I didn’t know is that Lily was horny af. In later conversations I learned that my confidence after having a girlfriend had been a turn-on to her – that I had seemed more mature and attractive. She was also somewhat possessive, and knowing that I liked her first (albeit years ago) seemed to have given her some primal urges to reclaim what was hers.

So, when she started grinding into my hardon ever so slightly, I started to get the hint, but stayed perfectly still, unsure what to do. She was moving almost hypnotically, and I started to grow more aware of her breathing as it grew shallower. I was also trying to see if I could hear Andy’s breathing. I couldn’t make it out – but I was hoping against all odds that he was unaware what his friends were getting up to in his new apartment.

After a few minutes, Lily slowed down (much to my relief). I reasoned that she was backing out of this – which was going to make things much easier for me (despite leaving me with a hardon). But then she turned around, and cuddled me differently – her head in the crook of my neck, her arm and leg draped across me, and her hips against the side of mine. While this thankfully relieved pressure from my cock (which was free to tent my boxers again) this amplified the amount of skin-on-skin attention, sending my imagination into overdrive. It also put her damned intoxicating scent all over me, which somehow drove my lust more strongly than her gyrating a few moments before.

But after a few minutes, she started gyrating again… this time pressing her mound into the side of my hip. It was at that moment that something registered that I’d missed when she flipped over. The front of her panties. They were soft. They were lacy. They felt skimpy. And they were wet. As she ground her mound against my boxers, I could feel her slickness through the fabric.

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Within a split second three things happened. She looked up. I kissed her. And she groaned – pressing herself more firmly into me before as our lips made contact for the first time. I was crossing a line I hadn’t intended to cross, cheating on my girlfriend – but in that moment the only thing that mattered was years of pent up lust being poured into one of the most memorable make out sessions of my life. It was fairly short-lived though, as I briefly pulled away to try and ascertain how aware Andy was of the situation.

I couldn’t discern any noise besides our own, so put a finger to her lips to encourage Lily to be quiet. Instead, she took my finger in her mouth and sucked it – mistaking my caution for foreplay and returning in kind.

I took my hand and moved it to her hair, grabbing it and pulling her back towards me to kiss. She attacked me with a hunger that I’d later become more familiar with, and after a few minutes of kissing and grinding, repositioned herself to straddle me.

Our underwear still on, she pressed down firmly on my hardon and started grinding up and down. I could feel my shaft being dragged between her pussy lips – her slick juices saturating the fabric of our clothing. Her hands were exploring me – one grabbing me by my wavy brown hair as the other traced over my torso. My hands were on her roaming her back and hips, feeling her soft skin under my fingertips. Meanwhile she kept grinding into me, bucking gently in a way that’s seared into my memory forever.

Her kissing become more feverish a few minute later. She started panting into my mouth, and finally bit down on my bottom lip *hard* as she started to spasm gently. As she orgasmed, I pulled her hips into me – letting her feel as much of my hardon as she had up until that point and holding her there until she had finished cumming.

After regaining her composure, she leaned up, and sent her hands downwards to my boxers, and felt my cock with her hands for the first time through the fabric.

I don’t know why, but it was at that point that my better sense came to the forefront of my mind, and I stopped her. I grabbed her hand, pulled her away, and just said “I can’t.” She understood. She was after-all my best friend, and knew that the man I was at that time was already uncomfortable about how much I had done. She crawled back up and lay her head on my chest, but kept some respectable distances at her legs and waist. I had a hardon for hours, but eventually fell back asleep.

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The next morning, we departed, and had a tense drive back. I have no idea if Andy ever knew what we got up to that night. I told her that I wasn’t really willing to talk about it with her yet. I ended up being quite late for work (by a few hours) and got appropriately chewed out for it.

After I finished work, I went to my girlfriend’s house and broke up with her. As a result, this is not the last story I’ll write about Lily and I…

Source: reddit.com/r/gonewildstories/comments/h7cqyz/my_first_time_cheating_with_lily