[M]y Li[F]eguard Trainer | 2016

It was the Summer before I left for college and had the cushiest job an 18 year old could have.... lifeguard! For anyone about to head to college you can't beat it... get a nice tan, make some extra cash, and have plenty of days off when it would storm.

I was a good boy in High School. I was not a virgin, but my sexual encounters could be counted on one hand. As mentioned in previous stories I was sort of the ugly duckling and din't blossom until my Junior year and wasn't the most confident guy. When I found out I was going to be working with Melissa it was exciting, but at the same time a bit intimidating.

Mel was much older and had a reputation. She wasn't the "college type" and had dated numerous local legends from star athletes to rich kids. She just oozed sexiness. She was 5'8 or 5'9, long blonde hair with just the right natural curl, piercing blue eyes, tan, and a very athletic body. Even her tattoos were famous. She graduated form a rival High School who were the "Tigers" and she had a tiger paw on her ass that anyone who knew one of her past boyfriends knew all about.

The first couple weeks I was borderline terrified of her, we would talk during breaks about small talk. Typically she would engage any conversation. I paid no mind to it, but soon she was purposely requesting the seat in the chair rotation that assured she would always have the same break as I.

Pool parties were the lifeguard's dream gig. You got paid overtime plus tips. Melissa had worked there for three years and had Seniority and thus the lion share of pool parties, she took everyone she could and she was my partner for my first pool party. Unlike during the day, our pool parties were super easy for the guards. Small groups we sat on the side of the pool instead of the chair. My first party was one of those and with kids all under 6 noone went to the dive tank thus allowing Mel and I to sit side by side.

She made the first move when she sat on the concrete between my legs and grabbed my hand and told me to massage her shoulder. I am sure it was the shittiest massage ever and I lingered entirely too long. During it the conversation on her end was much more pointed asking if I had a girlfriend, who I had dated, if I was a virgin, etc. When everyone cleared out that night she had the key to lock up.

I prepared to leave and said goodbye when she stopped me and told me to swim with her. I couldn't pass the opportunity so I did. It was innocent.. we horse played and splashed one another and she made me carry her on my back. It was still early in Summer so the evenings were a little cool, so when she got out she started shivering and I wrapped the towel around her and we kissed. Very sweet mushy stuff that makes you say "Awwwwweeeee".

Well then the story changed. We continued to kiss on the empty concrete and she began walling to the office. Once inside the door she immediately slid her bathing suit straps off revealing her breasts and sat upon the old steel desk. “Come here..” she said grinning knowing I was nervous. I went to kiss her again but instead she said “Kiss here instead” pushing me down to her breasts and tiny nipples. After my cumbersome licks and sucks began to make me more comfortable I could feel her hands moving as she peeled her bathing suit down her body and onto her legs. She grabbed my hand and put it onto the fabric urging me to take it the rest of the way and I did just that. She had a perfectly trimmed landing strip of brown hair and a 4 leaf clover tattooed right on the inside of her pelvic bone. She grabbed my hand again and proceeded to manually finger herself with my long fingers. She dictated the pace and the motion she wanted them to flutter about her lips.. she asked me to use my other thumb to play with her clit..reminding me to lick it before doing so. When she was ready for penetration she picked the fingers she wanted and the depth which they went. She told me how to motion my fingers inside and when I decided to be cute and try turning my hand while inside she sternly told me “Stop! ”. Soon I found the right combo and she was elevating off the desk and grinding onto me, supporting her body with both arms.

Then the magic words every guy lives for, “You have a condom?” I did not.. I had swim trunks! But, being 18 and with parents who were always at home, 75% of my hookups had occurred in my hand me down SUV so I knew there would be a condom in the glovebox. I literally sprinted to my vehicle. FUCK! MY KEYS! Sprint back inside as she laughs waiting there nude. Grab the condom..shut the door… sprint inside. I fumble with it trying to play cool (Why I was removing the condom while still in my shorts is beyond me), my hand shaking from adrenaline when I hear “Let me… just sit back” She proceeded to undo the string of my trunks and grabbed the waistband. “Let’s see what the cute guy has..” and then I had a moment of insecurity as my short slid down and my rock hard cock bounced back up and slapped my skin below my navel. What if I am little? What if it is ugly?

“Hmm….” She began making me even more antsy.

“Yeah…uh…that will definitely work” Shewww…. Victory!

She delicately took me in her mouth and licked up and down my shaft on both sides before rolling the condom down my shaft and pinching the tip that already had re-cum in it. She sat on the desk again and then laid back..moving the log book and pencils on the desk calendar. I inched close and she took me into her hand an did all the work guiding me to her little pink cunt. “I am nervous too…I like you..just relax and stay slow til I say so” Then she guided me in, inch by inch until I was about 1/3 of the way in. She then instructed me to slowly ease back and forth. With each stroke I felt her open up and me sink in. As I said she wasn’t the first, but with my others I was so excited to get in I rammed in like a bull in a China shop. She relegated my pace with her hands on my hips, biting her lip and looking at me in between moans. She continually complimented me on my size and told me how good it felt, building my confidence nad putting me at ease.

“Faster”.. I responded. “”Like this now” she rolled on her side and scissored her legs apart. “ Now fuck me..” she bent over the desk and elevated her ass…the famous tattoo! I pumped with all I had and felt my muscles burn I had never used to that degree. Soon she took control pushing me onto the desk and riding me from several different angles and intensities. The Gods of Sex must have had a plan for me that day as I should have never been able to last like I did.. I guess the excitement and adrenaline made me numb. With each position she took me further. Forcing me to pull her hair, grab her neck but telling me “not that hard” and “not that soft…just a little bit”. She finally must have settled upon my performance being satisfactory and simply instructed “Take Control..make me cum”

I bent her back over the desk and pulled her hair. I had never dirty talked during sex before aside from the standard You Like that” or “Feel good?”, but now I was saying anything that came to mind:

“You been waiting for a dick like mine haven’t you?!?!?” “You have wanted to screw (yes I used screw) me since you met me haven’t you?!?!?” “This is my pussy now ain’t it?”

I don't know what came over me but when she said "I'm cumming baby" some false confidence set in and I took control. I made her hold it, all the while pounding into her and pushing her head down with each stroke. Her screams louder and louder yet I keep urging her to hold it. I reached my hand around and pointed two fingers and she began sucking them ferociously like it was my cock..bobbing a couple times before screaming and begging for me to let her cum..before doing it again. Her body convulsed and my legs began cramping. Sweat poured down my face. Finally she pushed me out with her hands and released. "Taste me...please taste me" As I got onto my knees she literally forced me into her dripping twat. I thought she just wanted to give me the experience of tasting her cum, but she had other plans. She continued grinding on me like a slut in heat instructing me how to use my tongue on her clit. It was :45 that she was cumming again... a compound orgasm. After gathering herself she told me that was the first time she had been able to orgasm back to back and complimented me.

That Summer was a Summer of firsts. She taught me how to play with her ass, how to hold my own cum, my first facial, first time coming in a girl, first time I ever had sex in public. During "water safety checks" I would rub her pussy under the water while young kids ran around on the concrete feet away not realizing anything. We mutually broke up the week before I left for college. She visited a couple weekends the next semester before we slowly lost touch. She single handily gave me the confidence though I needed and taught me how to fuck.