I appreciate all of the comments and messages I received regarding my last story, and while I do not currently have an update for that story, I was asked by a few of you to write more stories about my sordid past. There are a few stories that I immediately thought of when I decided to write more. This escapade is special because it embraces the duality of being one of my favorite memories and one of my biggest regrets to this day. I hope you enjoy my mistakes. This was originally meant to be a single entry, but it became too long, so here is Part 1. Part 2 will be coming out shortly.
By the time I had reached my junior year of college, I thought that I had it all figured out. I was working 3 part time jobs in order to pay for my college, yet even though I did not have an abundance of free time, I still was able to go to parties, drink, smoke copious amounts of weed (this becomes important later), hang out with friends, and play intramural sports. In addition, I was acing all of my classes, I was in charge of the entire pool staff and pool maintenance at the college rec center, and I was getting a paper I had written published in a local magazine. I felt as if I were on top of the world. It was this arrogance that led to the actions and misdeeds you will soon read about. But I am getting ahead of myself.
I attended a small college, and despite it having a rec center and pool, there was no swim team. When I first started at the rec center as a lifeguard my freshman year, I noticed the disproportionate number of female lifeguards to male guards. I was one of four male guards on staff to the fourteen girls, and this ratio would only grow as I went through school. By my junior year, there were only two male guards on staff including myself. Of the twenty or so guards that were on staff, only about six of them had extensive guarding experience, and I was quite surprised to find out not all of the lifeguards were even passable swimmers. Almost all of our female guards were inexperienced and possessed a below average skill set, despite the requirement for the guards to swim a mile a week and monthly inservices. I met with the director of the facilities about this issue that I was having with my lifeguards. My solution was simple: create a recreational swim team for the lifeguard staff so that my coworkers could improve their swimming but in a fun and loose environment. My boss gave me the go ahead, and after filing all of the proper paperwork, the swim club was born. While it was not mandatory, this club provided a group atmosphere to perform their workout, and was initially quite successful. These practices always took place late at night after the pool had closed so that we would not disturb any other swimmers who were not a part of our club. We would often go out as a group after practice and grab food, watch a movie, play a board game, etc. After about a month, some of the lifeguards began to ask if they could bring their friends to our practices. I checked with the director and got his blessing to grow our team. I was ecstatic. My idea that I had developed five months ago not only was successful, but was beginning to blossom.
The first time I met Katie, I immediately liked her. She taught water aerobics at our pool for students, and became interested in our swim club when one of the guards, Miranda, had told her about it. I had seen Katie in passing before, but I had never really noticed her. She was a slight girl, standing about 5’5” but weighing less than 100 pounds and had a shy, quiet demeanor in addition to being accepting of all people. She had slightly wavy jet black hair that went halfway down her back, almost no tits to speak of, but a surprisingly toned ass that was amplified by her swim suit. I was at the edge of the pool talking to Michelle, a lifeguard that I was having an on again off again fuck buddy relationship with, when Katie came out of the locker room. Michelle only stood about 5’2” but she more than made up for her lack of height with the megaphone she called her vocal cords. She had very nice C cup breasts and long legs especially for her height. The tan lines that had been left by a different suit were still apparent, but I liked that she was not concerned about it and almost wore them as a mark of pride. In traditional swimmer fashion, her suit was very tight and I could clearly see her hard nipples poking through the thin fabric of the suit. However all of Michelle’s assets seemed to melt away when I spotted Katie out of the corner of my eye. I caught sight of her bright green swim suit, and out of curiosity I looked over. I was immediately enthralled by this girl walking onto the deck. I am not sure if it was the way that she took her glasses off and put them on the lifeguard stand or if it was how she shook her hair to gather it and put it in her cap, but something about her intrigued me.
“Mark! Are you even paying attention to what I am saying?”
The shrill voice of Michelle brought me back to reality with a sudden jolt. Michelle had a domineering personality, and coupled with her loud, squeaky voice, she was nearly impossible to ignore.
“Yeah, totally.” I lie. “I am hearing every word you say.”
“Oh shut up, you liar.” Michelle retorted as she pushed me causing me to lose my balance and go careening into the pool.
The cold water of the pool causes me to completely come back to reality as I come up sputtering and laughing. Everyone on the pool deck is laughing their asses off at me getting pushed into the pool. I look over to see Katie with the most perfect smile I have ever seen in my life. Her head slightly thrust back in laughter and her mouth parted wide allow for her musical laughter to be heard.
All of the other guards began to get in the pool, ready to do the workout that I had written earlier that day. I begin swimming the first set, getting used to the water and getting into rhythm. I thought that I saw a green suit swim by me on the opposite side of my lane, but I ignored it as we regularly circle swam to maximize our lane usage. I continue swimming the warm up set, oblivious to everything but my breathing pattern and the feel of the my arms pulling the water to drag me forward. Pull…Pull…Pull…Breathe…Pull…Pull… Bubbles? I crane my neck upwards and I see a pair of feet that are kicking and attached to Katie. She was swimming in my lane, but was not quite as fast of a swimmer as me, resulting in me catching up to her. I slowed down my strokes, content to swim behind her for the last 50 of my set. The way that she moved seamlessly through the water was intoxicating. I alternated between watching her swim in from of me and making sure that I was not drifting to the other side of the lane.
I finish my last lap without incident and grab a kickboard, ready to begin the kicking set. Kicking on a kickboard by yourself is one of the most boring and mind numbing activities one can possibly do. Kicking with a friend or two by your side, however, is a great way to socialize while putting on the guise of working out. I patiently wait for the other male lifeguard, Patrick, to finish up so we can kick together and shoot the shit. Katie finishes her swimming before Patrick though.
“Sorry about swimming so slow. I didn’t mean to interrupt your warm up.”
“Not at all, you gave me an excuse to slow down. I was just trying to impress you with my blazing speed.” I joke. Katie laughed that musical laugh of hers, and she flashed me her gorgeous smile.
“Want to kick together?”
“I would like nothing more” I respond in my best pseudo suave voice. We begin to our first lap, talking at first about our majors, classes, and professors, but eventually moving on to other subjects.
“Getting an A in Dr. Becker’s class is like the Cubs winning the World Series. Everyone always says that this is the year, but we all know deep down, that it will never happen.” She says to my statement about my classes in the upcoming semester.
Woah. This girl knows baseball? Me being the total sports junkie that I am, thinks that I may have just found the Holy Grail of girls. We continue to talk about sports, then we move on to TV shows, movies, comedians. We are cracking each other up, when she suddenly stops at the wall. I look at her questioningly, and then realize that we have kicked about 100 yards more that the set called for.
“I guess we should try and finish the workout, huh?” She says with a coy smile.
“Oh, yeah. Totally.” I respond. We finish the workout, hop out of the pool, and start walking on the deck to the locker rooms. I try making some small talk, trying to figure out if she has a boyfriend, and how my efforts towards asking her out would go. Not being able to pick up much, I decide to go for broke.
“Hey, Katie,” I begin. “Would you like to grab dinner this Saturday?”
“Yeah, that sounds great. I think that the college is holding a free ice skating night at the local rink Saturday night too, so afterwards we can do that.” Then she flashed me her smile. To this day I don’t know why, but that smile was sexier than anything I have ever seen in my life. The combination of her agreeing to the date, the sight of her dripping wet in her swimsuit, and her giving me a smile was enough to wake up my dick from its slumber.
“Cool see you then.” I try and play it off cool and get to the locker room without anyone noticing that my swim trunks were beginning to move on their own.
I quickly change and head back to my apartment, basically being gutted by my dick the entire drive. I go up the stairs, open the door, and immediately shut myself in the bathroom. Pulling down my pants, I begin to stroke my throbbing dick. I close my eyes and picture Katie in her swimsuit, me pulling it off, speculating about what lies beneath. I try to imagine what she was like in bed. I am imagining this small girl liking to be in control and riding me to climax. This is enough for me to finish as I ejaculate furiously into the waiting toilet paper.
Saturday cannot come fast enough for me, but eventually it arrives. I pick Katie up from her dorm, and I see what she is wearing. Knowing that we are going to the ice skating event afterwards, and given the fact that it is about 10 degrees Fahrenheit outside, she is wearing jeans and her parka. She gets in the car, and we go to a local Vietnamese restaurant that we both had expressed interest in trying. As soon as we are inside she takes off her parka to reveal a modest, but well fitting light green shirt that accentuates her body beautifully.
“Wow. You look amazing.” I say.
She blushes deeply and mumbles “Thanks” clearly embarrassed by my comment. We are quickly seated, and looking at the menu, when I say, “Hmmm that sweet and sour catfish soup looks good.” Trying to break the tension that I had unintentionally created.
Katie begins to laugh. “I was just about to say the same thing!”
We share a chuckle, but in reality, I just wanted to hear her laugh. The rest of the dinner goes wonderfully; I pay the bill, and we head to the ice rink. She is a significantly better skater than me, but she stays by my side, as I struggle to not fall down. This adds to the hilarity of the night, and before I know it, the night is over, and I am saying goodbye to her at her door. I move to give her a kiss, and she flinches. Scared that I had done something wrong, or misread the situation, I quickly try and backtrack.
“No, no it’s not you, it’s me. I’ve never been on a date before, or been kissed, so there are lots of new things that I am experiencing tonight.” She says, noticeably embarrassed, maybe even ashamed.
“Oh, I’m sorry. I didn’t know. I mean we don’t have to kiss.” Shit. I had no idea. And now it was really awkward. I said bye and left. When I got back to my apartment, I collapsed on my bed thinking about how I could have avoided the worst possible ending to an otherwise fantastic date. All of the sudden, my phone vibrated. Probably one of my friends asking how the date went. I didn’t really want to talk about it, but I figured I should check it anyways, just in case it was something important. It was Katie.
“Hey I am really sorry about tonight. Maybe we can try the ending again if you are still up for it.”
I stare at my phone, reading and rereading the message. Is she serious? I figure that I couldn’t fuck it up worse than it already was, so I text her back: “Yeah I would love to try it again.”
Five minutes. Ten minutes. Fifteen. Netflix plays in the background, but my eyes are glued to my phone, waiting for it to go off. Then I hear a knock at the door. I jump up to answer it. Katie was standing on my doorstep, cheeks red from the cold, and a touch out of breath. She must have walked from her dorm to my apartment. While it was only a few blocks away, in the current weather I was not expecting her to have made the trip, especially at 1:30 am. As a result, I end up standing mildly agape in the doorway looking like a fool.
“Can I come in?” She asks meekly.
All of the sudden I snap to. “Yes, of course. Sorry. You surprised me is all.”
I take her coat. She is wearing the same outfit she was earlier that night. I offer her a drink, but she declined, choosing to sit on the couch and watch Ferris Bueller’s Day Off that was playing on the TV. I sit down next to her, and wrap my arm around her. She seems to enjoy the contact and does not shy away from it. We sit for the most part in silence, watching the movie and getting comfortable with the proximity that we are to each other. The credits roll on the movie, then even the credits end, leaving us in silence. I look down at her as she looked up at me. I slowly dip my head towards her my lips finding hers. I kiss her gently, as she freezes for a second. I pull back slightly, and tell her: “You have officially had your first kiss. I’m going to be honest with you, nothing will ever be as good as that one kiss right there.”
I smile, and she laughs. The tension that was present is suddenly gone. She asks if we can go to my room so my roommate won’t walk in on us. I agree, and soon I am kissing her on my bed. With each passing moment, I can feel her become increasingly involved in the moment. Her hands still stay by her side, but mine do not. I embrace her as I kiss her lips and gently lay her back onto my bed. She follows my lead, wrapping her arms around my back. I begin to kiss her cheeks and neck which leads to her audibly sighing. I look up at her now flushed face as she drinks in the situation. I part her lips with my tongue as my hands brush over her small breasts. I feel that she has no bra on, and my fingers connect with her hardened nipple. I do not linger on her boob, but instead position myself on top of her and continue to kiss her lips and neck, lingering for half a second after each kiss. Katie is now breathing faster and heavier, the nervous rejection a few hours ago all but forgotten.
Her hands run under my shirt feeling my back and chest. I return the favor, sliding my hands under her shirt, exploring her tight stomach and toned back. I pause and take of my shirt, throwing it to the ground before resuming kissing her. Katie, copying my moves, begins to kiss my neck as well. Her innocent lips felt as if they were marking me as hers. I absorbed everything that she was giving me, and in that moment, I became acutely aware of my engorged member. I wanted, no I needed, to feel her tits right now. I move my mouth on top of Katie’s, interrupting her rhythm. She was momentarily taken aback, but then accepted my taking control. I reach down to the hem of her shirt and begin to pull it up. She props herself up, allowing me to take her shirt off. Her small breasts are out of the confines of her shirt. Katie laid back on my bed, her chestnut colored nipples erect and pointed straight up, begging to be played with. I oblige, taking each one in my mouth, using my tongue to circle each areola and then find the tip of her nipple. She was quiet while I did this, but her breath was becoming more rapid. With a nipple in my mouth, my hand reached down to unbutton her pants. I do, but then she says to me, “Can we leave my pants on tonight? I don’t think I am ready for sex.”
“Of course.” I say. Honestly this was way farther than I thought this would go tonight. “I won’t touch anything below the belt.”
Katie looked at me in a strange way. It was an odd union of relief and disappointment. “Well you don’t have to not touch anything… I just want to make sure my pants stay on.”
My hand slowly starts to stroke her crotch outside of her jeans. I feel the heat emanating from her. We continue to kiss as I rub her jeans. Even though she is enjoying herself, her slightly thrusting hips reveal that she wants more contact. I move my hand up to the top of her jeans and glide it down her pants. I am still on top of her black and white striped underwear, but the new feelings she experienced elicited an immediate reaction. A moan involuntarily escapes her lips as her hips rise to meet my hand. The juice from her pussy comes into contact with my fingers through her underwear. I seek out her clit and begin to rub it lightly over her panties. She momentarily stops kissing me to lean her head back in an attempt to regain some composure. This attempt serves to be in vain as I soon move my hand under her underwear. My fingers meet her dense hair, damp with perspiration and her own fluids. I reach her slit, tracing the outline of her lips, gradually slipping inside of her. I focus on her clit, gently massaging it. Katie is caught up in the moment, and I push one finger inside of her. Katie jerks up.
“Aaahh!” She exclaims. “You should go back to doing the other thing.”
I quickly pull my finger out of her and go back to playing with her clit. She lies back down, unconsciously starting to grab her own tits. I bring my mouth back to her nipples while I stroke her clit. She lets out a small gasp and tries to match the speed of my fingers with that of her hips. Her cheeks starts to turn red and her breath begins to become more shallow as she gets close to finishing. All at once, Katie grabs the bedspread with both of her hands, thrusts her hips into the air, and sucks in a deep breath and holds it. Her legs spasm, and I feel her pussy clench as she finishes for the first time in her life. She exhales almost with a whine as she lays on the bed, physically spent.
A bead of sweat accumulated on her forehead as she laid back on my pillow, a satisfied smile occupying her lips. I kiss the droplet of sweat and then give her a short kiss on the lips. She kisses me back and smiles. That moment was one I will never forget to this day as I got lost in that look of adventure and experimentation, trust and joy. I stand up and offer her a pair of sweatpants, although I tell her that I have no spare underwear for her. She giggles at my words, and graciously accepts the pants.
“Do you have a shirt that I can borrow to sleep in?” She asks.
“Sure.” I tell her, handing her my Led Zeppelin t-shirt.
“No way!” She exclaimed. “I love Zeppelin!”
“Could this girl be any more perfect?” I thought to myself as I watched her turn her back and put on the shirt I had given her. The pants I was letting her use billowed onto the floor; the six inches I had on her were quite apparent when she was dressed in my clothes. Somehow she pulled off the ensemble though, even posing in a ridiculous position for me. I cracked up, and I began to think, despite not getting off myself, I wasn’t resentful, or left wanting really at all. All I wanted to do was hold her in my arms, and take on any and all challenges that the world had to offer. Katie was mine, and I could not have been happier.
As Katie and I shared my small double bed, intertwined for both warmth and comfort, I could not imagine myself ever being happier than in this moment in time. I drifted off to sleep, wanting to lie there and breath in her scent forever. I kissed the back of her head and closed my eyes, looking forward to the future that we could have together.
Source: reddit.com/r/gonewildstories/comments/4dnuzp/euphoria_and_regret_part_1_m20f20