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High School Reunion Sex

woman in lingerie walking toward man in chair, high school reunion sex story 
High School Reunion Sex Story Submitted By Samuelle

I still cannot believe I went through with it. It was a day I had been simultaneously dreading and anticipating since the invitation arrived. The invitation had come addressed in my married name to a house that was now mine alone. I still remember pulling it back into my grasp moments before I let it slip from my fingers into the trash.

Despite deep reflection, I still have no idea what possessed me to attend, and more uncharacteristically, dictate my subsequent activities. Nevertheless, there I was sitting in my foyer, on my roller bag waiting for a cab to take me to the hotel where my 20-year High School reunion was being held. My nerves were noticeable as I bit my lower lip and jigged my leg, and queasiness settled in my stomach.

I sat waiting, reflecting on my 10-year high school reunion and the train wreck it was while wondering for at least the 100th time why I had chosen to go to my 20th. My husband had refused to go with me that night. His description of high school reunions was that they were "shit shows." He maintained the only people who went were losers who needed to feel better about their pitiful lives by comparing their marginal lives to others or have an extramarital tryst in the back of a rental car in the parking lot.

Curious and unwilling to accept his evaluation, I decided to go anyway if only to prove to myself that my class was different. However, I found they were not. Old clicks reassembled immediately, mocking and teasing the "UN-cool" people. Other attendees I encountered would begin a conversation with the perfunctory "what are you doing" question, and before you could complete a ten-word answer, they would interrupt and begin a 10-minute self-effacing description of their life. The sole purpose of this was to make you feel small and insignificant by comparison. So, after less than two hours of twaddle, I left, resigned that my classmates were indeed no different from those my husband described.

Upon my premature return home, I was rewarded with a condescending, demeaning lecture when I admitted he was right about the reunion. I should have stopped at a bar, or a friend's house had a few drinks and then gone home with alcohol on my breath and a wide smile on my face. That character trait was only one of the reasons I was now divorced. He was impossible to live with, often verbally cruel and generally unsupportive. Things I lived with because I was taught marriage was forever.

However, forever ended the day I caught him in my bed with our neighbor. After I unceremoniously ushered her from my bedroom and house clad only in her underwear, I calmly told him to get out. Initially, he blustered, countering that if I had "put out," he would not have had to look elsewhere. As much as that hurt, I knew he was right, but I also knew that if I spoke that I might forgive him. So I remained silent through his rant until through my tears, I mumbled that he could come back anytime I was not home to get his things. The only time I saw him after that was in the courtroom when our divorce was final.

I was snapped back to the present when from somewhere outside my current state of reverie, a horn sounded. I looked up to see the cab in the driveway. The trepidation that filled me earlier came flooding back as the front door lock latched, and I turned to make my way to the cab.

My nervousness made no sense; I was a wealthy, successful attorney in lucrative practice, and I still looked pretty good. My 38-24-36 figure was the envy of all my friends. Perhaps it stemmed from the fact that I was a recent divorcee, which to some, made me a loser. Maybe it was that I had decided to go all-in on the "reunion makeover," and I looked and felt as if I was looking at someone else when I stood in front of the mirror this morning. I had never been someone who agonized about my personal appearance. I was proud of the way I looked naturally, but admittedly, I had become more complacent about looks since the divorce. That is until I decided to go to the reunion.

In the last two months, I had improved my figure and was in the best shape of my life. I became an avid bicyclist, training five days a week and riding in every fundraising event I could enter. It didn't matter the length of the event or the cause. I entered and rode. I told myself it was my way of giving back, but the truth was I loved the solitude. I could ride without thinking about the personal life I hated and the sad looks and awkward conversations from friends who didn't know what to say or how to act. Maybe I rode just to get the free participant T-shirt, which now cluttered my closet.

The cab was making its way across town as I continued lost in thoughtful silence. A smile crept to my lips when I reflected on the fun I had preparing for this weekend's events and my reunion transformation. A new hairstyle, a professional makeup consultation, a manicure and pedicure, and lastly a Brazilian (not much fun), but I loved the feel and look of my pussy. I should have done it years ago; it made me feel sexy, desirable, and horny!

I desperately wanted to feel a man's silky shaft as it glided in and out of my smooth pussy. The newness and smoothness had driven me to multiple sessions with my favorite vibrator in the two days since the wax, ashamedly so much that I had to replace batteries; twice. While the vibrator felt good and helped me achieve orgasm quickly, I desperately wanted the closeness of another person, someone who would take me to a place no vibrator could and someone for whom I could lovingly return the favor.

I glanced out the cab window as it passed through downtown. My mind wandered to the shopping trip I took two days ago, and I felt a growing warmth and dampness between my thighs and heard a giggle sneak out from between my pursed lips. I was in the lingerie section looking for a few new undergarments when a middle-aged man with a kind face confronted me; I will call him Ken.

He approached me, asking if I would help him by trying on some lingerie he wanted to buy his wife for her birthday. He said he didn't know her size, but I looked to be about her same size and shape, although much younger, of course. He continued that their love life was in need of a spark, and it was his hope that something sexy would ignite her libido and passion for, "you know, sex!" I was skeptical about his motives, but the recent events in my life made me sympathetic, so I agreed to help.

Obviously pleased and very relieved, he handed me a charmeuse camisole and a pair of tap pants. A quick check revealed the size to indeed be mine. I retreated down the dressing room corridor to a room and pulled the curtain behind me. As I undressed, I took notice of my shape and form in the tri-fold mirror. The new hairstyle and professional makeup consultation accentuated my high cheekbones, green eyes, and long blonde hair. My 5' 6" body was tight, tan, and curvy in all the right places. I reached back and undid the clasp on my bra. I slid the straps down my arms and let it drop from my dangling fingers onto the dressing room bench.

Cool air washed over my bare breasts, and my nipples peaked from my shriveling areolas. I fought the urge to cup my hand under my breast and stroke the tightening nubs as I slipped the white camisole with spaghetti straps over my head before I reached down and pulled the tap pants over my thong. They, too, were white and had lace trim on the waist and high leg cuts. As I considered myself in the mirror, I noticed you could see my nipples and my red thong through the sheer material.

Resigned that it couldn't be helped, I gathered myself and bravely slid the curtain open before stepping into the dressing room corridor. In a feigned attempt at modesty, I held my arms in front of my breasts as I turned the corner from the corridor and into the store where Ken was waiting. A wide smile immediately filled his face. Seeing no one else in the area and suddenly feeling a little naughty, I dropped my arms and twirled, allowing him an unobstructed view of both the front and back of the outfit.

His louder than necessary affirmation that he liked it flattered me and led me to ask if there was anything else he would like to see. He responded by holding up another outfit, saying, "this one too, please." I held the baby dolls in my outstretched arm; they were more revealing than what I was currently wearing. The top was low cut in the front, the sides narrow enough to show part of my breasts, and a slit most of the way up the side exposed all of my hips and midriff despite ties that joined the front to the back.

I had been brave when I stepped from the corridor into the store wearing his first choice, but I told him if he wanted me to model this one, he would have to come into the dressing corridor and stand outside the cube where I was dressing. He agreed and followed me eagerly. As I turned to retreat to the dressing room, I could feel his eyes fixed on my ass. I smiled to myself and became a little excited by the experience. Suddenly I considered flirting with exhibitionism, so I decided to continue by tantalizing Ken even more. After entering the dressing cube, I slid the curtain only partially closed, giving him an unobstructed view while I changed.

Slowly and sensuously, I removed the camisole and tap pants. Once they were off, I stood in motionless in front of the mirror naked except for my thong. I smiled to myself as I heard a gasp from the hallway. Not wanting to be too obvious, I reached out and took the baby doll top from the hangar and over my head. The soft nylon material was teasing and taunting my swollen buds.

I elected not to put on the matching thong as I felt a sudden slickness between my legs. I used my fingers to adjust the front of my thong, grazing my bare pussy in the process. I drew a shuttering breath, and a wave of excitement shot up my belly. I hoped Ken was observing all this. I turned and slid the curtain open immediately coming nose to nose with Ken when I did. He jumped back, his face flooding red with embarrassment. My hopes were confirmed; he had been watching the entire time.

Feeling increasingly mischievous, I brushed the front of his bulging pants with my hand as I stepped into the corridor. As I walked away from him, the breeze from my movement lifted the baby dolls enough to expose my ass, which was bare but for the thong. I turned and walked back toward him, noticing he was having trouble breathing normally and was sporting a small wet spot on the front of his khakis.

When I was 6" from him, I stopped. His breathing was irregular as I leaned in and whispered that I loved this one. I backed up, propped my hands on my hips, shifting them repeatedly before I returned to the dressing room. This time I left the curtain open even more than before as I removed the baby doll top and dressed. I could feel his eyes on me.

After a 10-minute show, I leaned over to pick up my purse from the bench and heard Ken scurry down the hall in an attempt to conceal that he had been watching me. Walking down the corridor to enter the store, I was again aware of my slick pussy lips gliding past each other. I approached Ken, who stood with his hands in his front pockets, attempting to cover a cock that was straining against the front of his pants. As I passed, I paused and whispered softly in his ear that he really couldn't go wrong with either one before I kissed him on the cheek. As I walked away, a smile etched on my face, I could hear his crackling voice saying, "thank you."

From somewhere outside my current consciousness, I heard a voice calling for $41.50. Suddenly I realized the cab had stopped and was under the hotel portico. I gathered my purse and swung my legs out the open door, inadvertently exposing the waiting valet to my upper thighs and white thong. He smiled as he clutched my hand to help me stand. I smoothed my hands over my short denim skirt before I opened my purse, retrieved my wallet, and slid a $50 bill out for the cabbie who had retrieved my bag from the trunk and placed it next to the valet.

It was warm under the portico, and the valet led me quickly through the revolving front door, pausing once inside to point the way to the check-in desk. As I finished checking in, a different valet magically appeared with my bag, took the key card from the front desk person, and led me toward the elevators. I scanned the lobby as we crossed for familiar faces, seeing none I stepped into the elevator for the ride to my 8th-floor room. The valet inserted the key card in the slot and held the door for me to enter.

It was a large, tastefully decorated room. The drapes pulled back from the floor to ceiling windows allowing the brilliant summer sun to fill the room. The furniture consisted of a king-size bed, a couch, and a small desk next to an armoire. The valet set my bag on the end of the bed, I handed him a $10 bill, and he was off without speaking.

I slipped my shoes off and shuffled back toward the front door to find a full marble bathroom. It had a jetted tub, a separate shower, double sinks, a toilet, and a bidet. The hotels I stayed in when I rode in biking events certainly were nothing like this. Exiting the bathroom, I decided to unpack my things before the evening meet and greet that began in about an hour. The cab had been warm, and I was perspiring, undoubtedly as much from my anxiousness about the evening as from the heat. I decided a shower before I dressed was in order.

Without bothering to close the drapes, I pulled my top over my head, exposing my bare breasts before I hooked the waist of both my skirt and thong with my thumbs and simultaneously pushed them down my thighs stepping from the puddle of clothing after they fell to the floor. The warm water of the shower splashed against my neck and ran down between my breasts as I thought about the evening wondering what it surprises it might hold.

Who would I meet, and where would it lead? Would my classmates still be immature like they were at the ten-year reunion, or would it be different now that everyone was older and more comfortable with their lives? Would any classmates recognize the quiet, shy, studious, conservative girl they knew in high school who tonight looked like a provocative, elegant bombshell? Would they even notice the change? What was I trying to accomplish anyway?

Confirmation that at 38 and divorced, I was still desirable, or was it as simple as I wanted the closeness of the naked body next to mine and to experience the feel of a stiff rod inside my clean pussy. Either way, I was committed to attend as a transformed woman. While toweling off, I took notice of my newly clean pussy and couldn't resist sliding my hand over my smooth mons and along my folds. Without forethought, my fingers parted my folds, and I drew wetness from my pussy. I rubbed the moisture over and around my clit, my fingers gliding more easily as the wetness grew. I raised one leg onto the edge of the tub to gain greater access. I worked feverishly on my clit now as waves of pleasure built throughout my body. I climaxed in minutes.

The relief from my horniness was welcome, but I feared only temporary. I desperately wanted to continue with the vibrator I had in my bag, but I needed to get going. I rose from the edge of the tub, noticing my flushed cheeks as I passed the bathroom mirror. I planned to wear my new white thong under my garter and fishnet nylons, but with the lingering excitement from my climax, I decided to forgo the thong and just wear the garter and nylons. Now my bare pussy wouldn't dampen my new thong plus not wearing any underwear made me feel both naughty and sexy, primary objectives for my reinvented self.

I finished dressing, pulling my white shirt with a low scoop back over my head. My nipples were slightly visible through the soft fabric. I finished by stepping into a pair of 4" heels before I went back into the bathroom, brushed my teeth, and combed my hair. I stood in front of the full-length mirror across from the bathroom confident but nervous that I had the look I wanted before I grabbed my key card from the table next to the armoire and was out the door to the elevator. The doors to the hotel lobby opened a minute later, and I exited looking for a sign to the ballroom where the reception was being held.

Not seeing one, I decided to follow a group of people moving down an adjacent hall, talking loudly and carrying plastic cups that I assumed were filled with alcohol. As I followed them down the hall, I noticed a table outside a ballroom with a banner hanging from the front imprinted "welcome class of 1993". I quickly scanned the alphabetically arranged name tags for mine. Finding it, I pinned it to the strap of my shift and walked through the double doors into the ballroom.

I couldn't believe the crowd. My class was not this big; apparently, most people were escorted by spouses or significant others. Insecurity resurfaced, and I desperately wanted to turn and run, but with courage summoned from somewhere deep inside, I moved to the closest bar. As I stood in line, I scanned the room for someone, anyone I knew. No one looked the same, and since no one was immediately recognizable, I stood quietly in line, just trying to blend in.

After a 10 minute wait for a drink, I turned my scotch-neat in hand toward a wall where I could stand and scan the crowd for someone I knew when I felt the touch of a hand on the back of my arm. It was so soft it barely registered. I turned to see a man I immediately recognized as Sam before his voice queried "Hanna"?

Unable to think of anything original, I simply blurted out his name. His smile allowed the awkwardness of the moment to fade quickly as he asked if I would like to sit and talk. We moved to an unoccupied table close to the wall and sat. Naturally, the conversation began with the obligatory question, "what are you doing now." While I was answering, I was wondering how in the world he recognized me. I certainly knew who he was in high school, but nothing that happened in high school led me to believe that he knew who I was or that I even existed.

Sam was one of the cool kids, a basketball and baseball varsity athlete all four years, and the hunk that every girl in school lusted after, and some even gave up their virginity to. Now at my age, he was even more gorgeous. His brown hair was closely cropped, his brown eyes twinkled, and his tailored dark blue pinstripe suit accentuated his 6'5" athletic frame. For the next few hours, the conversation flowed effortlessly as we caught up and connected in a way I hadn't expected as if no one else was in the room. Soon the lights began to flash; the hotel's subtle indication that the event was over.

Sam suggested that we walk to the brewpub next door for a bite to eat. In addition to being hungry, somewhat tipsy, and not wanting the evening to end, I eagerly accepted. I held his folded arm as we walked through the lobby and next door. It felt so natural; he was a perfect gentleman. I was being seduced by his wit and charm. Over the next three hours, we ate and drank even more. I interjected sexual innuendo into the conversation on multiple occasions in the hope it would lead to something later. He would always smile but never respond directly to my sexually overt comments. This only heightened my desire for him.

I found myself fantasizing more and more about being intimate with him. It was during one of those moments that he announced that it had been a long day and he needed to get some sleep, before asking if I was ready to go. What could I say? I didn't want the evening to end, but I didn't really have a choice. We strolled back to the hotel, my arm wrapped around his, and my head tilted on his shoulder. It felt comfortable and right, but I was frustrated at not being able to gauge whether he shared my feelings.

As we stood waiting for the elevators, I was pleasantly surprised when he said how much he enjoyed the evening and asked if I would have breakfast with him in the morning. I accepted without hesitation. In the elevator, I reached to push the button for my floor just as he did. For the first time all evening, we touched. When the doors opened on eight, I stepped out, feeling his presence behind me. I turned a quizzical look on my face; he just said 826 and smiled. I stopped at 824, and he walked past me, stopping in front of the room next door. I stole a look his way as I slid my card into key slot our eyes meeting as he did the same. He smiled and said, "good night," and disappeared from the hall.

I pushed my door open and walked into the room, filled with mixed emotions. He was a perfect Gentleman, the kind of man I always hoped for, and one you want to take to meet your parents. While it was unexpected, refreshing, and noble, it was not what I wanted tonight. He didn't even try to kiss me goodnight. What was wrong with me? Was I not pretty enough? Was my new reinvented self to overt? Although I couldn't read his feelings exactly sure, he wouldn't have spent the whole night with me if he wasn't at least somewhat interested. I had hoped his suggestion that he was tired was only a line to get me back to the hotel where things would escalate physically.

I threw the key card on the table in frustration and plopped down on the bed. I sat there in silence, reviewing the evening's events and conversations, thinking about what I could have done differently to make myself more desirable to him. I second-guessed my appearance and every innuendo-filled conversation where I tried to make it clear I wanted him. After 20 minutes, I stood, mumbled, "fuck" and stripped. I pulled back the bedding and laid face-up staring at the ceiling. Despite my effort to reinvent myself as an available, sexually desirable woman, I was alone with no one to love again tonight. I hated my life!

As if suddenly possessed by a primal urge, I rose and moved to the connecting room door, which was illuminated by the lights of the city, like a summer bug drawn to alight. Without thinking I pulled, the door open knocked on the door to his room. On the 3rd rap, I panicked, what in the hell was I doing? I was standing naked, knocking on the door of a man I had really only known for the last 6 hours.

He could be married for all I knew since most of the night's conversation was about me. Just as I reached to grab the edge of the door and close it, I heard the crack of his door, and it swung wide open. Sam stood there clad only in his boxers while I stood there naked, frozen, a gut-wrenching silence hanging in the air, feeling more vulnerable, exposed, and slutty than I ever had. I was just about to slam the door and break into tears when he said, "My God, you are the most beautiful woman I have ever seen." Without another word, he moved into my room and wrapped his arms around my waist.

Breathlessly I stood motionless as his lips brushed mine and our noses touched. I was lost in the moment as he took his time, his lips roaming languidly over mine. I was melting in his grasp, my legs were shaking, and I was becoming faint as he pulled me firmly his erection-filled boxers. I could feel his heart beating against my chest. A soft moan slipped from my throat.

He walked me backward to the bed as he licked the lobe of my ear. My knees hit the edge of the bed, and I fell back, the cool of the sheets enveloping my naked backside. I giggled, and he laughed before he moved his open mouth over mine again. His tongue shot into my mouth, and I sucked it voraciously, wishing it was his cock. Sam broke our kiss and moved his head between my breasts. His scent was filling my nostrils. I closed my eyes and held his scent.

He massaged my breasts gently before he kissed my nipples that tightened beneath the touch of his tongue. I was woozy with excitement. I tilted my head back as I reveled in his soft touch that barely registered but so intense it raised goosebumps on every inch of my flesh. I began to sway beneath him as heat exploded in my pussy. He continued to alternate between my breasts with his mouth as his hand drifted along my torso to my inner thighs. His touch made me shudder, and I began to moan lustily. I pushed my legs apart to give him easier access to my dripping, ravenous pussy. But he just rubbed his hands over my thighs and my mons sending waves of desire up my belly. I wanted him inside me, but he continued to tease me working for his hands around my pussy but never actually touching it.

Climax was building rapidly inside, and I ached for him to be inside me. Just as I was about to beg him to mount me, I felt his fingers spread my pussy lips and place one on my clitoris. His stroke on my swollen clit sent me over the edge. Intense pleasure reverberated through my entire body. Losing control, I cried out, "don't stop; God don't stop." My body convulsed, my limbs turned to mush, and tears leaked from my closed eyes as I experienced the most intense climax of my life. Every cell in my body was alive. I wanted his cock buried deep inside me at that moment. I rolled him over and ripped off his boxers, exposing his throbbing steel rod.

Like the bedroom where I had suddenly become, I leaned in and licked the moisture that dotted the head of his purple throbbing cock. Now it was Sam who was spiraling out of control, he was groaning loudly as my licking and sucking sounds filled the room, and he cried out, "please fuck me NOW!" Finally, the words I had been waiting to hear! I rose up and squatted over his body, positioning my dripping pussy directly over his pulsating member.

I reached down and guided it into my sodden pussy as I dropped onto his pelvis. I began to move up and down, slowly savoring the feel of him inside me. His cock touched my g-spot as I ground my hips, and the feeling intensified. With his eyes fixed on me, he reached to caress my swollen tits. I reached down and rubbed my clit as I rode him with increasing speed and friction. No longer able to maintain control, I pumped hysterically up and down on his cock. Sounds of sex filled the room, my outer thighs slapping against his, the wetness between us oozing. We were so loud that I was afraid someone might call security.

No longer able to maintain my movements, he slid his hands under my ass and directed, not slowly but with urgency as he arched his back and pumped, slamming my pussy against his cock. We were out of control; I tensed as his cock pulsed, and he groaned loudly as he sent a hot stream of cum into my pussy. The flood of his warm cum caused me to come again, and I screamed uncontrollably as I orbited to orgasm. I continued to pump my pussy over his cock until it lost its rigidity, and it fell from me. I fell onto his sweat dotted chest, my body used, but in a good way.

Sam leaned in and kissed me tenderly, uttering the first words since he begged me to fuck him. "I guess we don't need two rooms for tonight." I smiled and responded, "I guess not unless you want to get creative."

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