[M18] Senior Prom Memory: Fingered My Date, Jerked Off With My Mate (Part 1 of 2)

Wow – I didn’t mean to take quite such a long stroll down Memory Lane, but once I started writing I just couldn’t stop! I shall therefore have to divide my story into two parts. This story takes place on the evening of my senior prom, but Kyle, Jenny, Chloe, Derek, and I were all 18 at the time. If you just want to read the naughty bits, you can skip down to the XXX.

I was raised in a small Midwestern town … I know what you’re thinking, but where I grew up isn’t what one usually thinks when the terms “small town” and “Midwest” are used together in the same sentence. It’s the county seat and second-largest municipality; it’s also near a large manufacturing plant and in the vicinity of several relatively well-known tourist attractions. All this has helped the town and its inhabitants stave off the kind of decay seen elsewhere in the state. I’m not trying to idealize it – the place certainly has issues. But overall, it’s a pretty wholesome slice of Americana and I consider myself fortunate to call it home.

I was a pretty normal teenager. By the time I finished high school, I was a little less than 6 feet tall and slightly on the thin side, with a mop of curly, light brown hair. Adults universally regarded me as a “good kid.” I was well-liked at school but not in one of the popular cliques, an above-average but not stand-out student. The only sport I did was swimming, and I wasn’t half bad by small town standards. Despite this, it was obvious pretty early on that I could never swim competitively at the college level. In terms of my romantic life, I had had a few long-term (for high school) girlfriends and done some messing around … however, none of these relationships had ever progressed beyond passionate groping and dry humping.

This story involves my friend Kyle, whom I first met when we were both sophomores. Kyle’s dad was an engineer at the manufacturing plant, and they had moved to town from a large city a few hours away. Kyle was a textbook example of a puberty “glow-up.” At 15, he was already 6 feet 4 inches tall but with a lankly, almost gangly frame. He also had pale skin, a bad case of facial acne, and large glasses. Kyle’s best physical feature was his jet-black hair, which he wore perfectly parted in a style reminiscent of the 1950s. That was how he appeared throughout the 10th and 11th grades – but the boy who walked into school on the first day of our senior year was almost unrecognizable.

Kyle spent the summer between his junior and senior years with his relatives in New England, who operated a marina. A few months of sun, salt water, and manual labor apparently did him a world of good … when he returned home, Kyle was tanned and muscular, having finally filled out; his skin was clear and he had switched over from glasses to contacts. Kyle’s new appearance came with a massive boost of confidence, and he made the lacrosse team despite never having been involved in sports before. I’m no lacrosse expert, but by all accounts he was more than decent. It wasn’t long before Kyle’s good looks and newfound athletic prowess began to attract female attention. Around Valentine’s Day, he began dating Jenny, a popular girl from the soccer team with a sunny disposition and a tall, athletic figure. I think it’s safe to say that Kyle fell completely head over heels in love with her. Though he would occasionally complain about her refusal to go beyond second base, I think he was just grateful to have a girlfriend.

The relevant portion of my story begins sometime in late March or early April of my senior year. Kyle and I, as well as another boy named Tim, met at our mutual friend Will’s house to plan our prom festivities. By this time, all four of us had already secured dates for the dance. Kyle would of course be going to the prom with Jenny, and Tim and his girlfriend would likewise be attending together. Will and I were both single and had asked platonic female friends to accompany us. Will would be taking a girl he knew from student government, while I would be accompanied by Chloe. Chloe and I lived on the same street and had known each other since we were kids. She was very cute and a lot of fun, but due to having grown up together, I had always seen her as more of a sister than a romantic prospect. Looking back, it’s painfully obvious now that Chloe had had a huge crush on me since at least middle school. I, however, was too stupid and self-absorbed to realize it … so, despite the story I’m about to tell, I can honestly say that I had no ulterior motive in asking her to be my date.

After several hours of discussion, Kyle, Tim, Will, and I agreed on our plan for the day of prom. First, we would all meet at Will’s house. His family owned an old farmhouse on several acres of land; the property was also partially wooded with a creek and several outbuildings. Seeing it for ourselves, we determined that it would be the perfect place to take our pre-prom pictures. We would then arrange for a limo to take us from Will’s house to a fancy steak restaurant for dinner. When we finished eating, the limo would pick us up again to take us to the location of the dance. That year, someone on the school board pulled some strings and was able to book a country club on a nearby lake. It was a fantastic venue … the only downside was that it closed at 11 PM. So, to prevent a bunch of wild teenagers from running amok, the school planned a prom after-party at the bowling alley in town. Although shuttles were provided from the country club to the bowling alley, we couldn’t resist one last ride in the limo. However, since the limo service didn’t run after midnight (small town family-owned business), we would have to arrange different transportation to get back home when the after-party ended at 3 AM.

A few days after our planning session, Kyle pulled me aside in the hallway at school. “So,” he asked in a conspiratorial tone, “what are you REALLY doing after prom?”

“Going to the bowling alley,” I responded, genuinely confused. “My parents are going to leave a car in the parking lot and give me the spare keys. That way, Chloe and I can just drive home whenever we feel like leaving.”

“And you plan on going right home?” Kyle queried.

“Why wouldn’t we?” I ventured.

“Well,” Kyle said, “I’ve been thinking … the dance ends at 11 … then the limo will bring us directly to the afterparty, which ends at 3. Once we show up at the bowling alley, no one will really be keeping track of us.”

“Where are you going with this?” I questioned.

Kyle’s voice dropped to barely above a whisper. “Alright Slade, I’ll be straight with you – Jenny and I are finally gonna do it on prom night. She wants the first time to be special, so I was thinking about getting a room at the bed and breakfast place by the lake. I figure we could make an appearance at the bowling alley, slip out around 11:30, get to the bed and breakfast, do the deed, and still be back home at a decent hour. Since people will have seen us at the bowling alley, we’ll have an alibi.”

I held up a hand. “Okay,” I said. “Congratulations … and it seems like you’ve really put a lot of thought into this. But why are you telling me?”

“Because,” Kyle began. “We don’t have a way to get from the bowling alley to the bed and breakfast and back again.”

“Ah,” I said. “So you were hoping to use my vehicle for your little sex jaunt?”

“Actually, I was hoping that you and Chloe would come to the bed and breakfast with us.” Kyle saw my mortified expression and hastily explained himself. “Not like that … I mean, you two could get your own room and whatever happens, happens.”

“How would we even get rooms?” I asked, confused.

Kyle gave me a tolerant look. “Don’t be an idiot, Slade. We’re all 18, and I’m sure you can scrounge up a couple hundred dollars in cash. No one will question a group of legal adults booking rooms for the night.”

“Maybe,” I said. “But your plan assumes that Chloe and I will actually want a place to mess around.”

“Do you not?” Kyle responded incredulously.

“Dude, she’s like my sister,” I shrugged. “I honestly don’t see her in that way. We’re going to the dance as friends, that’s it.”

“Unbelievable,” Kyle shook his head. “Alright then, will you at least consider letting us use your car after prom? I could have it back to the bowling alley before the afterparty ends.”

“I’ll think about it,” I said as the bell rang.

Fortunately, I didn’t have to think about it for too long because Kyle and Jenny broke up a few weeks later. The news was sudden – Kyle sent a message to our group text saying something to the effect of “it’s over.” He provided no additional explanation, nor were any of the rest of us inclined to ask for details. Apart from being concerned for Kyle, word of his breakup caused additional consternation to Tim, Will, and me because of how it could potentially affect our prom plans. At this point, we were only a couple weeks out. The limo had been rented, the dinner reservations had been made, the dresses and tuxedos had been fitted … lastly, but most importantly, the money for these things had already been paid. If Kyle or Jenny (or both) were to withdraw from our plans, that would only raise the cost on those of us who remained.

After a suitable period of time, I was given the unenviable task of questioning Kyle as to how his breakup would impact the group’s prom plans. I was relieved – but mostly surprised, to hear that everything would proceed according to schedule. Though the particulars now escape me, Kyle’s parents told him in no uncertain terms that he would not be permitted to “ditch” Jenny and “ruin prom for her.” I found this directive strange because he had been beside himself with grief in the immediate aftermath of the breakup. While Kyle had not told me or anyone else the reason he and Jenny ended their relationship, I would have thought that, given his reaction, the decision to do so wasn’t his. On the other hand, I couldn’t understand why Kyle’s parents would make him go to prom with a girl who dumped him … it was almost like a punishment, which meant they believed that he was mostly at fault. Despite the bizarreness of the situation, Kyle appeared to be at peace with it. I therefore elected not to press the issue.

At last, the day of prom arrived. Spring was in full bloom, and Tim, Kyle, and I arrived at Will’s house around 10 AM. We had a “guy’s brunch,” went swimming in the creek, and spent several hours playing videogames before getting ready. By the time our dates arrived from their own “girl’s day,” the four of us were looking like proper young gentlemen – freshly showered, clean shaven, and attired in our rented formalwear. We stood on the porch as the SUV carrying our dates pulled into Will’s driveway. I remember being dumbstruck when Chloe stepped out onto the pavement … I had always thought she was pretty, but at that moment she looked absolutely stunning. She wore a long periwinkle gown, and her coppery hair hung in loose curls over her bare, freckle-spotted shoulders. Never one to use much makeup, Chloe accentuated her green eyes with a light touch of eye shadow. Her dark red lipstick also provided a bold contrast to her pale skin. I followed the other boys off the porch and met her in the middle of the yard.

“Hi,” she said, not meeting my eyes.

“Hey,” I responded, temporarily lost for words.

“You clean up nicely,” she told me. When I didn’t reply after a few seconds, Chloe looked up and gave me a playful punch in the arm. “You’re supposed to return the compliment, stupid,” she said in a joking tone.

I certainly wasn’t joking when I blurted, “You look incredible.” She responded with a bashful smile and took my hand.

The next couple of hours passed uneventfully. We first spent an inordinate amount of time taking pictures at various locations around Will’s property. Several parents were in attendance for this portion of the evening, and they couldn’t stop gushing over how grown up their little babies were. This was mercifully cut short by the arrival of the limo, which then whisked the eight of us off to the restaurant. Initially, I had been afraid that Kyle and Jenny’s breakup would create some awkwardness in our group dynamic … but they were perfectly amicable toward each other – even affectionate at times. Given the events of the last couple weeks, their behavior struck me as odd. However, my preoccupation with Chloe prevented me from giving much thought to the matter. Dinner likewise passed without incident.

When we were finished eating, Kyle and I made a pit stop in the bathroom while the rest of the group went to the lobby to wait for the limo. As I adjusted my bowtie in the mirror, Kyle came to the sink next to me to wash his hands. He was grinning and quietly humming a merry tune.

“You seem awfully chipper for a guy who’s being forced to go to prom with his ex-girlfriend. What gives?” I asked.

“Jenny may be my ex-girlfriend,” Kyle said as he checked his teeth, “but I’m still going to fuck her tonight.”

“Excuse me?”

“Yeah man,” Kyle turned off the water and looked at me. “We actually talked on the phone for a while this morning. She said that she regretted breaking up because she really wanted to lose her virginity to a guy she cared about before going to college. She also said that she still cared about me even though we’re not together.”

“I’m sensing there’s more?” I queried.

“Basically, she left open the possibility that we could still have sex tonight,” Kyle began. “I didn’t mention it before now because it wasn’t a definite thing until a little while ago. When we were taking pictures at Will’s house, she told me that we should just go ahead with the original plan. She said she would rather her first time be with me than some random guy over the summer or in college. That’s why she’s been all over me tonight.”

“I thought it was strange that you two were getting on so well … and that explains a lot,” I replied. “But what about the room reservation?”

“Never cancelled it,” Kyle said. “Call me an optimist.”

“Do you have condoms?”

“Nah, she’s on the pill.”

“Well … shit,” I responded. “I guess this is happening.”

“There’s only one loose end – we don’t have a way to get from the bowling alley to the bed and breakfast place and back again.” Kyle’s face formed into a supplicating expression. “We were hoping you’d let us use your car.”

“Why my car? Is there really no one else you can ask? Surely there will be people at the bowling alley who drove themselves – what about one of Jenny’s friends?” I asked.

“Jenny doesn’t want word of this to get around.” Kyle shrugged, “You know how girls can be. Since you already knew, she said I should ask you again. Please man, I really don’t want to go around asking everyone … that’ll lead to way too many questions.”

“You’re really putting me on the spot here, Kyle.” I hesitated for a second before acquiescing, “Okay, I’m not gonna stand in the way of a friend getting his dick wet. Just ask me for the keys whenever you’re ready to leave … and try to be back at the bowling alley by 3.”

“You’re the best, Slade!” Kyle exclaimed as he pulled me into a hug.

“Wait, one more thing,” I said. “How’s Jenny getting back home from the afterparty?”

“There are a few girls from the soccer team who live out that way,” Kyle explained. “Someone’s coming to pick them all up at 3.”

“Makes sense,” I said, “But what about you?”

“Well,” Kyle began. “My dad was going to come to the bowling alley at 3 to bring me back home. But – if this evening goes as planned, I really don’t want to see him right after … ya know.”

“Yeah, I totally get it. Do you just want to crash at my place?”

Kyle seemed relieved, “I was really hoping you’d say that. Thanks, Slade.”

“No problem, Kyle,” I said as the two of us walked out to join the rest of the group.

About 45 minutes later, our limo pulled up to the country club. It was still light outside; though there was a DJ playing in the main reception hall, most of our classmates were congregating on the terrace overlooking the lake. Our group split up after we claimed a table. Some went straight to the dance floor, others went to find refreshments, and one or two went onto the terrace to find their friends. Apart from being with Chloe, nothing about the first portion of the evening really stands out to me. We didn’t see the rest of our group together again until about 9 PM. That’s when the principal got on stage and told everyone to go back to their seats while he announced the Prom King and Queen.

Once Chloe and I reached the table, we noticed that one member of our group was missing. I sat down next to Kyle and asked, “Where’s Jenny?”

He didn’t say anything; instead, he inclined his head toward the back of the room. I followed the gesture and saw Jenny at a table with several of the popular kids, sitting in the lap of a boy named Derek. Now, Derek was something of a legend – tall, blonde, and muscular, he was the very archetype of a high school jock. He had lettered in several sports and would be attending a large state university on an athletic scholarship in the fall. I didn’t know Derek personally, but he was a notorious ladies’ man. If the school gossip mill was to be believed, he had lost his virginity at the age of 13 and bedded every girl on the cheerleading squad. Accordingly to one particularly salacious rumor, Derek celebrated his 18th birthday by nailing his ex-girlfriend’s mother. I can’t attest to the truth of any of this, but you get the idea.

Seeing the pained expression on Kyle’s face, I attempted to spin the situation. “Huh,” I said, “Derek’s date is bound to be upset when she sees that.”

“Derek doesn’t have a date,” Kyle responded blandly.

“What?”

“Yeah,” Kyle continued. “He and some of the guys on the football team decided to go stag. Jenny’s been eyeing them since we got here.”

“Oh,” I replied, trying to be delicate. When Kyle didn’t say anything else, I leaned in close and whispered, “It doesn’t mean anything … you said yourself that you and Jenny aren’t together. Let her mack on anyone she wants – she’s still leaving with you tonight.”

“Yeah, you’re right,” Kyle said, though he didn’t sound convinced.

I gave Kyle a reassuring clap on the shoulder and turned my attention back to the front of the room. I can’t remember who was elected Prom King and Queen, or to what song they danced, but it wasn’t long before everyone flooded back onto the dance floor. I wasn’t particularly eager to go out again, but Chloe began tugging on my arm when a new song started. I smiled when I recognized the tune: “You Took the Words Right Out of My Mouth” by Meatloaf.

“Come on, we have to!” she urged.

“Very well,” I sighed in mock acquiescence, allowing myself to be pulled from my seat.

Chloe and I were both fans of 70s and 80s music, and Meatloaf was one of our favorite artists. As the song played, we flung about, spinning around and mouthing the words to each other. By the time it ended, we were both giggling, sweaty, and out of breath. It was with some relief that we greeted the next number – a slow song, “Soul and Inspiration” by the Righteous Brothers. I pulled Chloe close to my body and placed my hands on her hips. She draped her arms over my shoulders and rested her head against my chest. We rocked back and forth for a minute or two before she said, “Your heart is pounding … I can feel it.”

“Mmm hmmm,” I agreed. I started to bend down to say something into her ear, but Chloe chose that exact moment to look up at me. Our eyes met, and I was suddenly speechless. Not knowing what else to do, I reached up and brushed a strand of moist, coppery hair from her forehead. She reciprocated by cupping my left cheek in her right hand. Then, almost by instinct, we both leaned in for a kiss – our lips touched briefly before we pulled apart.

“What was that?” I asked, nonplussed.

Chloe beamed, looking triumphant. “Something I’ve wanted to do for a very long time.”

“Why am I just finding out now?” I responded lamely. Though I had always viewed Chloe as a friend, it was clear to me then that she wanted to be something more. I inwardly kicked myself … How could I not have seen this? How could I have been so obtuse? Luckily, her gaze brought me back to the moment before I could sink into a spiral of self-recrimination. As I stared into the sea-green depths of Chloe’s eyes, it was like I was truly seeing her or the first time. Suddenly, the idea of us being together seemed so natural, so undeniably correct. That realization spurred a previously unknown desire from the depths of my being. Whether these feelings had always been lurking in my subconscious, or only came into existence in that instant, I didn’t know – nor did I care. I simply gave in and bent down for another kiss.

As Chloe and I became more intimately acquainted on the dance floor, the pathetic saga of Kyle and Jenny continued to unfold elsewhere. I’m eternally grateful that I wasn’t present to witness any of what happened, but others filled me in on the details later. After the prom king and queen were announced, Jenny, Derek, and Derek’s group of friends left the reception hall and went onto the terrace. Kyle followed, approaching Derek and Jenny as they stood by the railing. Kyle asked Jenny to come with him somewhere more private, saying that they needed to talk. Jenny announced loudly that anything Kyle had to say, he could say in front of Derek. At this point, Derek placed his arm around Jenny, effectively daring Kyle to try and take her.

There are several versions of what happened next – none of which reflect well on Kyle. In the account that I find most believable, he then asked Jenny, “Why are you doing this? I thought we were supposed to be together tonight?”

Jenny laughed, “What on earth gave you that idea?” Kyle’s face turned red and he began to sputter helplessly. “Besides,” she continued, “I can’t be with you.”

“And why is that?” Kyle finally managed to get out.

“Because,” Jenny said as she looked meaningfully at Derek, “the two of us are an item. How long has it been now, babe?”

Derek smirked, “Oh … about a month and a half.”

I can only imagine how devastated Kyle was to learn that Jenny had been hooking up with Derek since their initial breakup. As the realization dawned on the group that had formed to watch the confrontation, a low snicker began to rise up from the crowd. Kyle stood frozen to the spot as the laughter increased in volume, soon accompanied by jeers and pointing fingers. Unable to endure any further humiliation, he finally gave in to his fight or flight reflex. I would like to tell you that Kyle avenged his honor by beating Derek to a pulp – but high school isn’t a fairy tale, and Kyle was still very much a shy, nerdy kid at heart. So, he turned on his heel and bolted from the terrace as fast as he could, finding shelter in a deserted billiards room for the remainder of the evening.

Chloe and I remained on the dance floor from our kiss until the dance officially ended about an hour later. During that time, we didn’t see Kyle or anyone else from our group. A little before 11 PM, the chaperones began herding students out of the main reception hall and into the parking lot. Those who would be taking the school-provided shuttles to the afterparty were told to form a queue, while those had arranged their own transportation were given directions to the bowling alley. Since Chloe and I were among the last people out of the building, I fully expected that everyone would already be at the limo by the time we made our way there. My assumption was mostly correct – however, once we all piled inside, I again noticed that our group was one short. For the second time that night, I asked, “Where’s Jenny?”

Tim, Will, and their dates stared at me, aghast. Kyle folded his hands and looked at the floor as the limo started and began to drive away. Chloe, likewise clueless to the drama that had unfolded earlier, demanded, “What’s going on?”

“Didn’t you guys hear?” Tim finally spoke up.

“Hear what?” I questioned.

Tim cast an uneasy glance in Kyle’s direction. “Jenny left with Derek. They’ve been … uh … seeing each other for about a month and a half.”

“Wait,” I said, “That means …”

“It means,” Kyle responded without looking up, “that Jenny and Derek started fucking literally the day after we broke up.”

“Dude,” Will interjected, “You don’t know that.”

Kyle straightened and looked Will in the face. There were no tears, but his eyes were noticeably red. “Don’t be a child, Will,” he said harshly. “It’s Derek, we all know he wouldn’t bother with a girl unless she was putting out.”

The truth of that statement was so obvious that no one dared to contest it. In the quiet that followed, Kyle reached into the ice bucket and helped himself to some sparkling cider. He poured the effervescent, golden liquid into a champagne flute and studied it against the light.

“Well, cheers to senior prom!” he announced mirthlessly. Kyle then took a sip and sighed. “God damn, what I wouldn’t give for some real booze right now.” The rest of us simply sat there in silence, not knowing how to comfort our friend.

After what seemed like an eternity, the limo finally arrived at the bowling alley. This was actually a very large space with several dozen lanes, an arcade, a restaurant, and a lounge area. When our group walked in through the main entrance, we immediately noticed Jenny sitting at a lane with Derek and several of his friends from the football team. Seeing us, Jenny wrapped her arms around Derek in a proprietary fashion. Derek then turned his head in our direction and, after making eye contact with Kyle, began to shamelessly make out with Jenny. Kyle stood in place, watching the scene unfold with a stony expression.

“Why don’t we all head to the restaurant and get some dessert?” Will suggested cheerily. “I’ve heard this place has awesome milkshakes.”

“Sounds like a great idea,” seconded Tim.

“Nah, you guys go ahead,” Kyle said blandly. “I’m going to hit the arcade.”

“Are you sure, buddy?” I asked.

“Yeah,” Kyle continued with a discernable note of bitterness in his voice. “Wouldn’t want to be the seventh wheel. I’ll catch up with you guys later.” He turned and walked away without another word while the rest of us looked at each other helplessly.

“What should we do?” Will’s date said once Kyle was out of earshot.

“What can we do?” Tim responded. “I say we give him some space. He needs to process this in his own way. He’ll talk when he’s ready.”

Agreeing that this was the best course of action, the six of began walking in the direction of the restaurant. However, Chloe tugged on my arm, holding me back. “I’m not really feeling ice cream right now,” she said. “Looks like there’s music and dancing in the lounge – let’s go check it out!” So, we again parted ways with our friends.

The lounge was separated from the rest of the bowling alley by a pair of tall, leather-padded doors. Inside, the large, rectangular room was decorated to look like a 1920’s speakeasy. Black-and-white pictures covered almost every square inch of wall space, while mismatched couches and chairs were grouped in a semicircle facing a central stage and dance floor. At the opposite end of the room, a bar that normally specialized in draught beer served an assortment of mocktails to its underage clientele. The lounge was also very dark – dim table lamps and light reflecting from a hanging disco ball provided the only illumination.

There was a DJ on the stage and maybe ten or twelve couples spinning around on the small dance floor. “Let’s go!” Chloe yelled, pointing at the middle of the room.

“More dancing? Aren’t you tired?” I asked.

“Not at all … unless you want to wear me out?” Chloe responded suggestively.

I smiled at her cheekiness. “Oh, that can be arranged.”

XXX

Chloe and I danced for a few songs, but it wasn’t long before the lounge began to fill up. Agreeing to a break, we made our way towards the back of the darkened room, hoping to find a place to rest. Most of the seats we passed were already occupied by other couples, but we soon found an overstuffed chair directly opposite the stage. While large, the chair itself was still too small for two people to sit comfortably side-by-side. Feeling confident, I plopped down, spread my arms, and gave Chloe my best seductive look – inviting her to sit on my lap. Chloe clasped her hands to her chest in a dramatic swooning motion before tumbling into the chair. She landed in a heap on top of me, and we both laughed as we struggled to arrange ourselves with some dignity.

As she was trying to make herself comfortable, Chloe’s round little butt ground into my crotch … being a healthy teenage guy, that was all that was necessary to make my penis swell – within seconds, I was sporting an obvious erection. We both immediately stopped giggling. I turned my head away in embarrassment, not daring to look her in the eye. Chloe, however, wrapped her arms around my neck and whispered in my ear, “Looks like someone’s excited.”

“Sorry,” I said in a penitent whisper. “Damn thing has a mind of its own.”

Chloe pulled back and gave me a considering look. In a tone that was both admonishing and encouraging, she said, “Don’t apologize for being a man, Slade.”

Taking this as permission, I pushed myself up and locked lips in a passionate embrace. As I supported Chloe’s back and shoulders with my left hand, I cupped one of her breasts with my right. Her boobs were small and perky – perfectly suited to her petite frame. Running my fingers over the silky fabric of Chloe’s dress, I became acutely aware of the fact that she wasn’t wearing a bra. I felt her nipple stiffen at my touch, gently tweaking it between my fingers. I smiled inwardly when this action elicited a small shudder from Chloe. I clearly wasn’t the only one who was excited!

Chloe then attempted to shift her position in the chair. However, rather than straightening herself, her torso fell onto my chest and her legs began to slip. To prevent her from falling to the ground, I reached out and grabbed her knees with my right hand, pulling her lower body back onto me. As I did, I noticed that her dress had hitched up, exposing the skin of her right knee. Once I made sure she was stable, I tentatively moved my hand from cloth covering her left knee to the bare flesh of her right. Feeling the difference in sensation, Chloe glanced down for a second before looking back to my questioning face. She didn’t say anything; instead, she opened her legs slightly, inviting me to explore further. My eyes remained fixed on hers as my hand crept slowly up her thigh, ready to retreat at the first sign of protest.

None came … within moments, my right hand and forearm had disappeared under her dress. It was at that point that I reached a satin barrier I immediately identified as the fabric of her panties. I also noted with some satisfaction that there was already a damp spot in the front. Nonetheless, I was still anxious about exceeding my mandate; rather than push forward, I paused and gave the fabric a little tickle with my fingers. At this, Chloe groaned slightly; then, she hitched herself up and gripped my upper arms with both hands. She leaned in close so that our foreheads were practically touching. “Go on,” she encouraged in a sultry voice.

I found the edge of the fabric and peeled it sideways, exposing her pussy to my touch. The skin of her vulva was soft, warm, and smooth. Chloe began to breathe heavily as I rubbed my thumb up and down her moist slit, spreading her juices. Although I was a novice in the art of pleasing women, I wasn’t completely unaware of what I was doing. Thanks to an inebriated rant from one of my older brothers, I knew that girls masturbated by stimulating the clitoris … so, I figured that I could get Chloe off by rubbing it. I continued to feel above her opening, looking for what my brother had described as a “bean.” After a couple of passes with my thumb, I detected a hard little nub I identified as my objective. Having resolved on a course of action, I began to trace light circles over her clit with my thumb as I probed her opening with my middle finger.

As I worked my middle finger inside, I watched carefully for any expression that might signify pain or discomfort. At first, Chloe was impossibly tight; but, as she became accustomed to my touch, she opened just enough to allow my finger to enter. I thought briefly about attempting to try two fingers, but I dismissed the idea almost immediately for fear of hurting her. Instead, I slid my middle finger in and out of her pussy to a depth of about two knuckles; meanwhile, I continued to rub her clit with my thumb, gradually increasing the speed and pressure. In these efforts, I allowed Chloe to be my guide – if she was unresponsive to one thing I did, I tried another … but if she moaned or writhed with pleasure, I kept at it. Soon, she was moving her body up and down in tempo with my finger, riding my digit as it penetrated her.

She couldn’t have lasted more than a couple minutes. I suspected she was close when her grip on my shoulders began to tighten. I asked, “How does that feel?”

“Slade,” she panted into my ear, “I’m gonna …”

“I know,” I said. Then, in a raspy voice I barely recognized as my own, I commanded, “Cum for me.”

Chloe buried her face in my jacket – at the same moment, I felt her vagina clench around my finger. This was no dramatic screaming orgasm. Even still, I felt a surge of masculine pride as the sound of her faint, muffled squeal made its way to my ears. It was the first time that I had ever been the cause of another’s sexual gratification … and it made me feel like a god!

As the sensation subsided, Chloe slumped against my shoulder, completely spent. We sat together for a little while in silence, taking stock of what happened. Then, she straightened herself and looked me in the face. I greeted her with a wolfish grin.

“You’ve done that before!” she accused.

I shook my head, and as I did so I finally pulled my hand out from underneath Chloe’s dress. I held it up for us to examine, my fingers glistening in the lamplight – still slick with her fluids. Seized by some atavistic impulse, I moved it to my mouth … Chloe’s eyes followed the gesture with titillated curiosity while I sucked her juices first from my middle finger, then from my thumb. As I took in her sweet, metallic taste, the pure eroticism of the moment caused renewed bloodflow to my groin. My erection, which had subsided somewhat in the aftermath of Chloe’s orgasm, came roaring back with new life.

Chloe noticed immediately, smirking as she grabbed my waistband. “Your turn,” she said lasciviously.

I placed a hand on her wrist to prevent her from going any further. “No,” I replied. “Not here – it’ll be too obvious and make too much of a mess.” Seeing the disappointment on her face, I continued. “Don’t worry, babe … we have all night, you have plenty of time to make it up me.”

Chloe gave a petulant huff and fell back against my chest, feigning annoyance. Knowing she wasn’t actually upset with me, I began to tickle her side. She attempted to swat my hand away – but I persisted. Soon, she was giggling happily and turned her head back to give me a peck on the cheek. I reciprocated, and we sat there for some time exchanging kisses, whispering to each other, and watching our classmates on the dancefloor. It was perfect … until Kyle came up from behind and awkwardly tapped me on the shoulder.

Source: reddit.com/r/eroticliterature/comments/jxe9jq/m18_senior_prom_memory_fingered_my_date_jerked