My Freshman Year

When I woke, he was gone, had I dreamed this encounter? Was it just wishful thinking? I wondered out to the hall where Josh was saying hey sleepy head get washed up and we’ll pick up breakfast sandwiches on our way. I took a quick shower and got dressed as I headed down the stairs, Josh had a gym bag he was taking to the driveway, I went outside as he locked the door behind us. He had his dad’s car, a late model Mercedes SUV, he said because his dad had parking garage permits, so we wouldn’t have to worry about paying or finding parking.

I was amazed at the city and the skyline, everything was tight and compact, but tall and cramped. Our first stop was Battery Park we walked around and viewed the Statue of Liberty, then to Grand Central station, Brooklyn Bridge, World Trade Center site. Then we drove through China Town, Little Italy, and Greenwich Village, where for the first time in my life I saw guys walking hand in hand, and an eclectic neighborhood, as we ate some lunch in a small luncheonette. We were definitely in a gay area, was Josh looking for a reaction? He even pointed out couples and we passed some unique sexual orientated shops and stopped into them, but they weren’t your seedy sex porno shops, they were boutique type places. Again I was hard and horny just with the suggestive materials out in the open, I had never seen such materials out in the open, things I’ve only seen on the internet.

We drove uptown to Times Square, 5th Ave, Empire State Building, Rockefeller Plaza, St Patrick’s Cathedral. Round about 3 or 4 we parked and visited a museum possibly the Guggenheim? where we stopped and spent a lot of time in an area of Mapplethorpe photos of mostly nude men and couples, in suggestive sexual poses but not really pornographic, we stopped and sat facing one of Josh’s favorites of two nude males. He put his hand on my thigh and began rubbing it asking my opinion as he turned and looked into my eyes, it was here I knew we was prompting me to finally make a move, or he was about to give up, but I could tell, the tease phase was now over. We stood to leave, as he said let me show you Central Park, I stood with him, began to follow his lead, as I lowered my hand and took his hand, he wrapped his fingers into mine as we looked at each other and made our way to the exit.

We walked hand in hand through the park, stopping at a grassy field overlooking the lake where Josh pulled a blanket out of his backpack and laid down, in the warm Indian summer dwindling heat, I laid next to him as we talked and stared at the surrounding areas. Josh switched positions and me on my back, he on his side, rested his head on my chest as a pillow. As he held one of my hands and said, “I waited for you, I waited till you were ready, I almost gave up hope, I thought you were interested but I didn’t want to push you, I gave you all the signals I could, I almost gave up”. I acknowledged his advances and explained my shyness toward the situation. We continued to lay there through sunset as he rolled over pressing closer to me, looking toward my crotch, running his finger over the outline of my dick, saying “it feels nice, I don’t usually move this slow, but there was something about you that made me proceed with caution”, he didn’t want to screw this one up, he said “I was different, innocent and he wanted me”. I acknowledged I was a novice, and very scared, and I’ve never ever tried anything with another guy, and hell I never even did anything with a girl, other than self gratification I was new to it all, just a back woods farm boy from small town mid America.

It was getting late about 7 or 8, we drove back to Times Square at night, grabbed some dinner and watched the people and lights, back to the car and the long trip back to Josh’s house. In the car we talked, but now it was more of a personal situation, more intimate, I thought to myself tonight’s the night, in the past 3 weeks I found someone, visited New York City, and was finally going to have the chance for my first sexual encounter. As we approached Josh’s driveway around 10:30 or so, there was a car there parked behind his, he said “oh my mom and dad are back”, and like that my thoughts and visions shrunk back inside my brain much like my dick in my pants. Josh pulled his dads car back into the garage.

We entered the house from the garage side door that lead into the kitchen, where Josh’s parents were sitting having a drink at the center island, Josh’s dad stood, as Josh introduced me to his mom and dad. Josh’s mom replied ah….so this is the infamous Dave we’ve heard so much about, as his dad raised his hand for me to shake as he eyed me up and down, returning to his drink. His mom questioned “Josh… you were into the beer again”? He immediately replied yeah we had a few beers with some pizza in the pool last night, his dad said “you know I don’t mind, but I don’t want you driving if you had, and especially my car”. Josh assured his dad it was last night and we spent the day in the city on his parking pass, and his dad seemed to be content with that answer, and why shouldn’t he as it was the truth. I admired Josh for being as open with his parents as he was.

With that he bid his parents good night saying we’ve had a full day in the city and fresh air, and we were tired, as his mom gave him a kiss on the forehead and a brief one armed hug, his dad was taking another sip of his drink as he waived the two of us away. Josh lead me upstairs as he peeled off into his room, and I proceeded straight toward my guest room, he paused, reached out grabbed my hand and said no, pulling me into his room. I protested, “But your parents”, he said “no worries, they know”. In amazement I said unconsciously know what? As he sat me on his bed, taking his shirt off, “that I’m gay, and they’ve caught me with guys in my room before”, and frankly he suspected they assumed he’d be spending the night with me, “they already know everything about you that I’ve told them already, my parents are cool, no worries”.

He sensed my nervousness and said in a calming voice, no worries Dave I’m in no rush, we’ll go slow. As he now in his briefs tugged my shirt off as I kicked my shoes off and he pulled my jeans off. He climbed under the covers, and flipped them open on the opposite side inviting me in. I lay next to him barely able to make out his face in the dark, but I knew he was facing me and staring at me as he fidgeted with my hair. Quietly I asked if he joined me in my bed last night or was I dreaming it, he acknowledged yes he did for about 3 hours, “but you were sleeping so soundly I just enjoyed touching you, and you never woke up”, I admitted I did when I rolled over, he said he hoped I would but assumed I didn’t, anyway he admitted he enjoyed it and decided not to freak me out and he left before I woke. I smiled and admitted I would have raped you, how could you show such restraint? He said now don’t get scared, but I’ve had a lot of flings and I’ve regrettably bedded guys just for sex, but you’re  different, you’re a challenge, I feel something for you like I have never felt before, why do you think my parents already know about you?

With that he reached down and ever so gently touched my dick through my briefs and I was rock hard, he raised his thigh up onto my thigh as he continued to massage my dick, eventually sliding his hand under the waistband. Another guy was now touching my hardened dick head, with an ever so gentle touch of his fingertips. I was breathing extremely hard, as he raised and put his head on my chest, I felt the weight and the hair as it tickled my skin. He admitted he wanted to touch me in that Speedo last night, as he continued to push my briefs down further fondling my dick and eventually my balls. He slid the covers off to the side, as our eyes were adjusting to the dark, my dick was throbbing with my balls over the waistband as he fingered my stomach as well. I was ready to burst and he knew it, as he moved to other areas to touch, then back onto my dick, I moaned “No” he said “Yes it’s ok” and he continued as I spurt up over his face, I’m sure the first shot hit his hair, the next few volleys fell short of his face just onto my stomach, as he remained ever so still playing in the fluid with his finger never letting go of my dick. He turned his head over now looking in my eyes, I felt the fluid stuck in his hair touch my chest as he sandwiched it between us. Quietly he stared into my eyes and smiled, as we quietly drifted off into sleep.

My first real experience was a one way experience, him touching me, I still haven’t touched him, but I was content, I loved the feelings I was having, another guy has touched me and brought me to an unconditional orgasm, holy crap I was in ecstasy.

About a half hour later, he repositioned and laid next to me, still staring at me, he asked if I’d ever been kissed. Reluctantly I said well, a girl once, but it wasn’t a true kiss, although it was on the lips it was more like a mom or sister kiss, not quite as innocent as a cheek kiss but very similar. He replied no guys then? I quickly said “hell no”. With that he leaned in and kissed my lips saying, “like that?” I said “yes”, as he leaned in repeating it again and again, and then he opened his lips and gave a slight suck on my closed lips, and then ran his tongue around my lips, first the top then the bottom, when he then ran his tongue through the split, gently splitting them open, encircling my inner lips and I could feel his tongue touching my teeth. Immediately I panicked, my breath, my cotton mouth, but he continued to prod into my mouth when his tongue made contact with mine, I began to tongue dance with him. This was a first for me and all so new, yet I took his lead and was thoroughly enjoying it, as was he. We were biting each other’s lips and spreading saliva on each other’s faces, as our hands were encircling each other’s heads, and mine were stroking through his hair. He sunk his tongue deeper as he twisted sideways and suddenly I began gagging when he pulled back, each time he attempted to slide deeper in and pulled it back out, it felt as if his tongue was actually into my throat. So much, all so new, and oh so good.

Josh rolled to his back interlocked his fingers with mine, and eventually raised my hand and placed it on his briefs, where he released it, allowing me to feel his hardness through his briefs as I squeezed it, not really knowing how to do this, other than my self gratification methods, but I wanted it to be good, so I did what I liked, but felt I was rushing it, I grabbed, I was anxious, I wanted it, I wanted him Cumming in my hands, I dove into his briefs with my hand as he grabbed my wrist and began mouth kissing me again, this action immediately slowed me down as he removed his hand from my head and slid down his briefs , Josh is now naked as I fondled his dick and balls while he was deep throat kissing me. Before long he whispered to stay right there and keep that perfect rhythm because he was ready to cum, I paused and asked if he was sure and he brought his hand to mine to make me continue, before long he was spewing his load between us, pumping globs upon globs onto each of our bodies.

He wrapped his hands around my chest hugging me in his cum as I hugged him back continuing to kiss me, where we fell asleep. My first gay sexual encounter was mutual masturbation, and a kissing lesson I’ll never forget, and the feeling of fulfillment and comfort as well as the warm human touch of another body entangled with mine.