Sex in the Sky

“My initial story told of my first experience with another man. “My Cross Country Adventure” detailed my evening with Walt, the elderly gentlemen who picked me up while hitchhiking and taught me a great deal.

This story tells of my further explorations in this way of life. One thing I should have mentioned at the top of the last story was that these events happened in the late 70’s; a time when there were far fewer health concerns than there are today.

I encourage you to read the previous story, but it is NOT necessary in order to be able to read and hopefully enjoy this one. Don’t be put off by the 3 pages, as the last page is only one paragraph. Thanks!”

*************

1. College.

After making my way out to my brother’s place in Wisconsin without any further problems, I made the necessary arrangements for school and then investigated the area around Milwaukee. I was still reeling from my incredible evening with Walt, and I was unsure about exactly what I was.

I had always been attracted to girls, and those feelings were still there. Men were another thing. I had never been attracted to men, or so I had thought. Yet, the more I thought about it, the more often I remembered looking at other guys changing in the locker room at school.

I also remember the couple of times I got stuck taking a shower when the gym teacher would insist upon everyone doing so. He even took roll call as you went in, as if you could work up a sweat standing around for a half hour waiting to take a couple of swings at a softball.

Those times were hell, especially when I realized how shortchanged I was in the penis department. When I saw those guys walking around with their cocks swinging I covered myself up as best I could and took the shortest shower imaginable, followed by a quick exit to get my underwear on at top speed. The humiliation was unbearable. Mind you that people never said anything, probably because they didn’t get a good look, but just the same I dreaded it. I took no measurements, but I sure did peek, and I never saw any guy with a smaller dick than mine.

This had a great effect on my love life, as you might guess. I got a hand job from a girl once, and she didn’t say anything bad, but she probably wasn’t all that excited because we stopped seeing each other after that.

From then on, I figured that I needed to find a very innocent girl; one who hadn’t seen very many men before. Marry her before she knew how she was getting cheated, and live happily ever after.

After being with Walt and seeing how little importance he placed on the size of my dick, however, I started to think that just maybe I had been looking in all the wrong places for love and affection.

I recalled that evening often and how much I enjoyed holding another man’s cock; how good it felt and how erotic is was for me. The fact that Walt was so well developed had frightened me at first, but that became a source of excitement as the night went on. When he ended up taking me, the pain was intense but so were the thrilling feelings that came with it. I lost track of how many times I got myself off during the ensuing weeks just thinking about it.

2. Changing myself.

One thing that came of that night was my desire to get into better shape. The sight of me naked in the mirror in all my pudgy glory made me determined to get in condition. I took to running around the campus, and while it was tough at first, once the weight started coming off it became easier. I lost the 25 pounds I was aiming for plus a few more. Now when I stood naked in front of the mirror I looked a lot more presentable without my pot belly.

Another thing that had always bothered me was my hair, or lack thereof. I had no hair on my chest, and my legs had only the lightest dusting on the insides of my lower calves. I could probably have easily counted the few hairs under my arms, and the little tuft around my dick was next to nothing. I didn’t have to shave my face more than once a week either.

The decision took a long time to make, but the actual shaving didn’t take more than five minutes. When I got finished, the only hair on my body was on the top of my head and my eyebrows. Everywhere else was smooth as silk.

My reflection in the mirror was a jolt at first, but the more I looked, the more I liked what I saw. Besides, the absence of hair around my dick made it look bigger. Well, maybe not bigger, but at least you could see all of it now.

After admiring the new me looking back from the mirror, and recalling Walt and that night, a few seconds of pulling on my dick got it hard, and so I began to jerk myself off. I looked at my reflection in the glass as I did, and only the acorn shaped head of my dick was visible with my hand wrapped around it. Nothing to be done about that, I thought to myself as my fist began sliding up and down my dick harder.

Better to finish this in the shower, I thought to myself, and as I stood in the warm spray and rinsed the remnants of the shaving cream off my body, I brought myself to a nice orgasm, all the time thinking about Walt and the incredible things we did together.

3. The mixer.

I saw flyers posted around campus for a mixer being thrown by the gay and lesbian alliance and took note of the time and date. It certainly seemed like a possible way to meet a guy, since at least you didn’t have to worry about whether someone was gay or not if they were there.

I dressed neatly but casually in the new clothes I had been forced to buy with my weight loss. Wearing 32 waist jeans was something I hadn’t done since I was 12, and I looked okay in them, although stuffing a sock down in front might have helped the look a bit.

Outside the place that the mixer was being held, I watched as people went in. Most of them just walked right in without a care, while I stood outside trying to make sure no one saw me go in. Finally, after walking past the door for the umpteenth time, I turned abruptly and bolted in.

Inside there were about 100 people standing around talking and listening to the records a guy was playing over in the corner. A girl asked me my name and promptly slapped a big smiley face sticker with TIM written on it in big bold letters. I got a drink and wandered around the room, trying to figure out what to do next.

“Having fun yet… Tim?” a tall husky guy said as he came up to me from the side. I had already heard his distinctive voice rising above the din earlier, and now I saw the face connected with the voice.

“Not yet, but I’m hoping to uh…,” I offered lamely while looking at his name tag. “Doc,” I said while finally finishing the sentence.

“Well, at least you still have hope,” Doc bellowed with a boisterous laugh. “Most of the rest of us here have no hope. I’m sort of the chairman of this sordid group, and it’s my fault you’re standing here in this wake. I know you don’t come here often, because I would have remembered.”

“No, it’s my first time.”

“Dear.”

“Excuse me?” I asked in confusion.

“Deer. You look like a deer caught in the headlights.”

“Oh! Sorry.”

“No, please don’t apologize,” Doc said. “I love the shy and innocent type.”

“That’s me I guess. I don’t even know if I should be here or not.”

“Why? Are you FBI or something?” Doc chuckled.

“No, I’m just confused about who I am, or what I am,” I finally said.

“Join the club Timmy. You don’t mind me calling you Timmy do you?” Doc asked and continued without waiting for me to answer. “Most everybody here is confused, and the ones that say they aren’t confused are liars. College is a time for figuring things out, and getting to do it on the folks dime is a bonus.”

“Doc. Is that your real name?” I asked.

“Might as well be, because that’s all everybody calls me,” Doc said. “I’m pre-med, but I’ve been called Doc for almost my whole life.”

“From the cartoon… you know, What’s up Doc?” I suggested.

“That would make for a more socially acceptable story, but I got tagged with that moniker because I’ve always loved giving physicals to guys.”

“Good practice for the future I guess.”

“You could say that, but I was doing it long before I knew my ass from my elbow,” Doc said and exploded with laughter. Doc’s laugh was contagious and I couldn’t help but join him.

“I’m a deviate, but a likeable one,” Doc said as he patted me on the back.

“Maybe I’ll make an appointment with you sometime,” I told Doc. “It’s been a while since I’ve gotten a check up.”

Doc’s laughter faded away and he looked at me with a glint in his eye.

“No appointment necessary for you Timmy,” Doc said softly. “In fact, if you want to stick around until this thing ends, maybe we can go have a drink afterward.”

“Okay,” I heard myself saying, and Doc smiled and headed off to try and get his party energized.

I watched as the very genial Doc went from group to group while I finally started breathing again. I guess that I had just been flirting with a guy for the first time in my life, and it appeared that I had succeeded. Doc seemed like a really nice guy and at the very least the night might be entertaining.

Doc was a big guy, that much I noticed from standing beside him. He was about four inches taller than my 5′10″ and had a husky build, much like mine, or should I say like mine used to be. I guessed him to be in his early 20’s, which made him about 4 or 5 years older than me.

Doc had carrot colored hair, cut a little shorter than my just over the ear look. His meaty arms were covered with hair, and the fur on his chest was peeking out from the open neck of his shirt. He was just a big old teddy bear, and as I watched him work the room my imagination worked as well, wondering what the rest of the night would bring.

4. Doc’s place.

I helped Doc wrap up the mixer, and found myself walking up the stairs to his apartment soon after. He had a small but neat apartment, and as Doc got us a couple of drinks, I looked at his record collection. It was mostly jazz, and I recognized a few as ones I owned.

“You a jazz fan?” Doc sai from behind me as he handed me a beer.

“Some of it. I love Bitches Brew,” I said pulling out the album. “Weather Report. Stuff like that.”

“A fusion man,” Doc said with a chuckle. “Sounds good to me. Now if I could only get you to relax.”

Doc stood slightly to my side and behind me, and I could feel his breath on the back of my neck while his hand gently kneaded my shoulder.

“Sorry,” I said as my heart went up to my throat. “I’ve got to be honest with you. I’ve only been with one man in my life.”

“It must have been good for you, or else you wouldn’t be looking for more,” Doc whispered into my ear.

“It was,” I admitted.

“Tell me about it,” Doc asked while I looked blankly ahead at his record albums without seeing them. “Don’t spare any details, and talk dirty too. That really turns me on, and believe me just looking at you already had me turned on plenty.”

“You really want to hear about it?”

“Hell yes,” Doc said as he nuzzled the back of my neck, causing my whole body to shiver.

“I was hitchhiking after I got my bus ticket stolen and this elderly guy picked me up and drove me west a few hundred miles. He got us a motel room and after we went to bed I felt his hand on my hip.”

“Oh man, I’m going to cream in my jeans any minute,” Doc said as his hand slid down my back and squeezed my ass.

“He reached down and grabbed my dick and started to jerk me off.”

“Then what happened?” Doc asked.

“I came. Then he went down on me and I came again.”

“And you liked it?”

“God yes!” I exclaimed. “It was the first time my dick had been in a mouth. Then he put my hand on his cock.”

“How did it feel?”

“Big,” I said.

“Mmmmm… you like the big cocks then Timmy?” Doc said as he rubbed my back.

“It was the only one I’ve ever touched, so I don’t know,” I confessed. “I did like that one though. Problem is, everybody else’s cock looks big to me. I’m really small.”

“Oh yeah?” Doc asked. “I’m not. That okay?”

“Yes,” I croaked meekly.

“Here,” Doc said as he took my free hand. “See what you and your story have done to me?”

Doc brought my hand down and put it on his crotch. I felt the thick bulge in his jeans and my hand slid down to follow the outline. As my hand finally reached the end of his cock well down the inside of his thigh my breath caught in my throat, creating a sound that matched the nervous way I felt.

“Omigod.”

“What else did you two do?” Doc said as he rubbed up against me some more.

“He put a finger in my ass, and then another one,” I said rather breathlessly. “Then he put his cock in.”

“You let this guy put his big cock in your ass?” Doc said. “How did it feel?”

“It hurt. It hurt real bad,” I recalled. “But then it started to feel okay, and by the time he came, I was sorry it was over.”

“Oh you are such a naughty boy Timmy,” Doc said. “Anything else happen?”

“He let me stick my dick in his ass.”

“You did? You liked it?”

“Yes, but I liked jerking him off while I did it just as much,” I said. “I put his cock in my mouth while he was asleep, but I never got the chance to really do it.”

“Never sucked a cock before?” Doc said, and I shook my head no in response. “How would you like to suck on mine? I’d love to be your first.”

“I’ll probably do it badly, but I want to try” I said.

5. Doc’s bedroom.

Doc brought me into his bedroom, which was covered with posters of a wide spectrum of topics from music to nature and everything in between. The light stayed on, which made me a little uncomfortable at first, but things were happening so fast I had no time to react.

Doc brought me over the the side of his waterbed and took my hands in his and put them on his chest. My fingers were trembling as I fumbled trying to undo the buttons, My ineptness caused Doc to smile as he watched.

“You’re so sweet Timmy,” Doc said. “I don’t care whether you’re an actor or just really innocent. You’re turning me on like I can’t believe.”

“No act,” I muttered in frustration. “Nobody could be this lame on purpose.”

“Not lame Timmy. Sweet. Just take your time man. We aren’t going anywhere, or at least I hope not, and I’m not laughing at you.”

I managed to eventually get all the buttons of Doc’s shirt undone and pulled it off his beefy shoulders. His upper torso was completely covered with thick red hair. My hands ran through the dense carpet, and as my fingers ran over Doc’s plump nipples I watched them blossom before my eyes. He was a little chubby but fairly solid, and had to be the hairiest man I had ever seen.

“Not exactly Charles Atlas, am I?” Doc asked.

“You look nice,” I said. “Feel nice too,” I added while running my hands over his shoulders. Impulsively I raised his arm and buried my face in the thick tuft of hair that fairly exploded from Doc’s armpit. When I kissed and licked the lightly scented fur and heard Doc groan, I knew that I was doing something right.

My hands fumbled with Doc’s belt for a moment before Doc gently pressed down on my shoulders. I went to my knees and worked on opening the buckle. I could have done a better job with it but I had a lot of trouble keeping my eyes off the absurd bulge that commanded my attention. There was a slight damp spot right where the bulge ended which I found exciting to look at. I suspected I had a stain of my own by this point, because my dick was pulsating with excitement.

The belt opened up and I pulled Doc’s jeans off with his help. Doc’s legs were coated with more of the brilliant orange hair that he was apparently covered with. He was wearing white boxer shorts with red stripes. They were not the real long and baggy variety, but it was still an unreal sight when I saw the pink tip of his cock peeking out of the leg opening. A strand of precum hung off the end, and my finger swiped at it before I reached up for the elastic of his boxers.

My hands were now shaking so badly that I was getting dizzy looking at them. I undid the clasp at the top and slowly pulled them down. As they came down, the thick pelt of hair continued until just above his cock, where it seemed that Doc had shaved around the base of his member.

Doc’s cock was pinned down along the leg of his boxers, and as the shorts came lower it came into view. The base of his shaft was thick and actually seemed to get thicker as more was revealed. When I got the boxers down past his cock, it sprang up wildly in response to being freed, almost clubbing me in the chin as it swung upward.

Doc’s cock was breathtaking, and the gasp that exploded out of me when it was exposed was unintentional but honest. Doc’s gigantic cock bobbed in front of him much like a diving board being jumped on. The impossibly long and almost inhumanly thick tool arched slightly upward toward his navel, exposing the richly veined underside and the pale white skin stretched so taut that it seemed ready to tear from the strain. The gentle upward curve also exposed Doc’s pendulous scrotum, which was as outrageously oversized as the rest of his equipment. The way he had shaved around the base of his cock made it look even larger than it was.

I looked up at Doc, who was smiling down at me, clearly enjoying my look of awe which I couldn’t have hidden if I wanted to.

“You do like the big cocks, don’t you Timmy?” Doc asked while he cradled the back of head and pulled me toward his tool. “Show me how much you like mine. Just watch your teeth.”

I didn’t need any encouragement, and I leaned forward, letting my tongue slide along the underside of his cock right down to his balls before retracing the path right back up to the tip. My tongue dabbed at the cum which was leaking out of the opening of his cock, and it tasted musty but not unpleasant. I dragged my tongue up and down the underside, which not only made Doc groan but kept the precum oozing out of him. My fingernails ran up and down his furry thighs as I licked away.

This teasing was not only fun for me, it also bought me some time, as I tried to figure out how I would ever be able to get Doc’s huge cock in my mouth. The head was bulbous to say the least; the pink crown was the size of a plum and the ridge of it flared out widely.

When I finally touched Doc’s cock for the first time he groaned loudly. My fists squeezed the shaft tightly, and I gently twisted my hands as I pumped him. My lips slid up the head of his cock, and I tried to keep my teeth from scraping the bulb as I took him in. Once I got the head inside my mouth, I began moving my lips back and forth over the ridge, unable to take much of the shaft beyond that. I tried to make up for what my mouth couldn’t do by using my hands on the rest of him.

I knew that I was doing something right, because Doc was grabbing handfuls of my hair and breathing heavily. His knees buckled a little and he suddenly yelled out to me.

“Arrrghh…cumming.”

I had so little warning that I had no choice about what to do. I felt him spurt into my mouth, and the roof of my mouth absorbed the first few blasts. Another spurt went down my throat which almost made me gag, but I put my tongue over the tip of his cock. This diverted the force of his orgasm, and I managed to keep him in my mouth while his ejaculations eventually subsided.

Doc pulled me up to my feet and kissed me, his tongue dancing inside of my cum-filled mouth, while his hands clutched my buttocks. The slightly sour taste of his cum was not unpleasant at all even after his tongue spread it around my mouth.

“If that was your first head, you are going to be unbelievable in no time,” Doc said as he held me close.

“I think my jaw is dislocated,” I said as I flexed it to get it back into alignment. “I guess that there are big cocks, and then there are BIG cocks. Your cock looked so amazing that I wanted to take all of you into my mouth so badly.”

I got to the restaurant a few minutes early and found her already there, as I approached the table she quickly gathered up some papers she had been studying and shoved them into her purse.

The conversation kept coming back to me and my career even though I was much more interested in finding out more about her, it seemed a bit odd to me that very afternoon she didn’t know me from Adam, but now she seemed almost an expert, then I caught on, “Sarah, I hate to ask this, but those papers you were reading when I got here, were those crib notes about me?”

She turned bright red, and nodded. “I just wanted to have something to talk about.”

I leaned across the table and put my hand on hers, “Can we talk about you instead? I already know all I need to about me. Tell me about yourself.”

Sarah took a deep breath and countered, “I’m not that interesting really.”

“That isn’t true. For example, how do you like running a club?” I asked.

“Well you know how musicians are, most of them wouldn’t know how to make a living out in the real world. They’re the most spoilt bunch of prima donnas, and think the world should revolve around them and their ‘art’.” She stopped and looked at me completely horrified, realising what she had just said, “I’m sure you’re the exception!”

“Sometimes.” I laughed.

With little prompting on my part she opened up and told me her entire life story, the rest of dinner I barely got a word in edgewise but despite all that I was captivated, and looked forward to seeing her again.

The Love You Make

It was the oddest chance that made me see the ad for his one off show. I was actually trying to see what Sainsbury’s had on sale that week, I almost missed it but the photo in the corner caught my eye. It was a great picture of him, just him and his guitar posed up against a brick wall.

Why was he doing a solo show without the band? And what the hell was he doing playing some dinky club that held less than 500 people? After all this last tour he packed in twenty to thirty thousand a night. I stared at his picture, the way he had of looking at the camera like a lover. I knew that look he had given it to me more than once.

“Stop it!” I said aloud, “he’s not yours anymore. Deal with it.”

Not that he ever really was.

I told myself I wouldn’t go to the show, obviously he had moved on and it was up to me to do the same, but of course Saturday rolled around and there I was lining up with the rest of the people hoping to get in.

I saw him arrive; I ducked back in the shadows as he walked past me. He turned and looked in my direction with a slight frown but then some cute little blonde grabbed his arm and led him into the club.

I was one of the lucky few that got in, there was a mad rush for the front of the stage and the place was filled to the rafters. I managed to get a spot two rows back.

He took the stage at 10 pm; there was a collective gasp and then cheers. I had only seen the performances from the back of the stage. I knew he drew the audience in but seeing it from their point of view I could really understand why he had such a following. Even in the crowd I felt like his songs were being sung just for me, and by looking at those around me it was clear that the feeling was shared.

During one of the sad ballads he stood on the edge of the stage and looked into the audience, his eyes widened when he finally saw me. At the guitar break he looked straight at me again as if he was trying to memorize where I was.

As the set wound down I started to make my exit. I wanted to leave with the crowd but I didn’t want to miss a note of the song so I just slowly moved to the back of the club. I had almost gotten to the door when a fight broke out near by. Two rather drunken women were loudly arguing about something and they effectively blocked the doors.

By the time the bouncers separated them the show was over. The place emptied out pretty quickly, and I had congratulated myself on making a clean get away until I rounded the corner heading to the underground and he stepped out of the shadows directly in front of me.

“Did you enjoy the show?” he asked, as he lit a cigarette.

“It was very good, I’ve said it before boss, you are talented.”

“I really didn’t expect to see you tonight. You almost made me forget the lyrics to my own song.” He laughed, and then he got serious, “So how have you been Paul?”

“I won’t lie, I really miss you.”

“I miss you too.” He dropped the cigarette and crushed it out with his shoe, “I would like to be your friend do you think that’s at all possible?”

“Do you mean hanging out at the bar type of friends? Or playing darts kind of friends, or friends who occasionally fuck the hell out of each other?”

He smiled, “You always had a way with words. Let’s start with the first two and see if we can do that.”

“And then?”

He brushed his hand across my cheek, “and then, well, then we’ll just have to play it by ear.”

Part VII: The Next Steps

Over the next several weeks, I found many opportunities to get away either from work or, in the evenings, away from home to see Andy. In each encounter, I would continue to explore more interesting aspects of the act of sex between two men. Andy was an able teacher and the result was that I was letting him lead me down the paths and pitfalls of learning to enjoy fully the experience.

As time flowed on, I was becoming totally infatuated with Andy and feelings akin to love were rising. Each time I came close to proclaiming such fervour, I ’stepped back’ and gathered my thoughts. For one thing, I was concerned about family issues (my wife and children would surely be deeply wounded to learn of the directions I had taken); secondly, Andy had never shown anywhere near that level of commitment.

One day, as we lay exhausted together in Andy’s bed after a prolonged sessions of loving, Andy raised the subject of unvisited territory – anal penetration. To that time, mutual fellatio had been the primary focus of our times together. When he whispered to me as I lay in his arms that he wanted to make love to me, I was taken aback. I wasn’t sure if I could stand the pain and I was also totally unsure of how one went about it. However, it was his term ‘make love to me’ that won me over. When I asked him what he meant by ‘love’, his response was that it was strictly his term for penetration. When I looked visibly unhappy with that explanation, he asked me what was troubling me.

Hesitantly, I tried to explain. I was certain that he would either laugh at me or end the relationship if I blew the next part.

“Andy, I have never been as happy as I have been with you” I stopped his interruption with a finger on his lips. “Let me try to say this. Not only have you taught me to relax with my feelings and instilled a sense of confidence that I have never enjoyed, I have also become very, very attached to you. The feelings I have scared me at first but as I started to think on it – and I have done a lot of soul searching – I have come to realize that what I am feeling is very like…ah.”

“Would you be trying to say the “L” word” Andy smiled.

“If you mean love and not some other ‘L’ word, then I am afraid you’re right. Does that mean we’re over?” I fearfully asked.

“Actually, no” Andy assured me. “I have been trying to think of a way to bring up the subject myself since I share your feelings, babe”

We hugged each other tearfully and kissed as we whispered breathless words of love to each other.

“Can we seal this with a true expression of my love for you and your faith and love in and for me?” my lover asked. “I can promise that I would never hurt you; do you trust me?”

“Yes, of course. But I don’t know what I need to do”

“Not a thing; just relax and let me lead the way. If I start to hurt you, simply ask me to stop and I will.”

Part VIII: Love Consummated

Andy proceeded to kiss me from my brow to my feet and back again as I slowly relaxed my whole body for him. As he reached the juncture of my thighs, I spread myself wide as I have grown accustomed to doing. As a result, he gained free access to my balls and perineum; I had learned what a pleasure it was to have the latter kissed and loved and my cock reacted immediately. This time was different; Andy went further than he had done before until he was licking and circling my pucker with his pointed tongue. As his talented tongue pressed inwards on my anal ring, I pressed down to relax it and I felt the heat of his tongue invade me for the first time.

It felt wonderful and I showed my pleasure with an almost constant stream of moans and cries of “Oh yess, Baby! That feels so great!”

Andy continued to tongue-fuck me for a few moments and then, using some of my precum – I had been flowing in copious amounts – as a lubricant, he slid first one and then two fingers into my ass. Oh lord, it felt so great; I tightened my grip on those invading fingers by clenching my anal walls; I didn’t want them to be freed! We had often in our times together, experienced the pleasure of digital anal penetration while we sucked each other but this was different. Perhaps, it was because I knew what was to come and my senses were highly attuned to the anticipation that those fingers would soon be replaced with my lover’s cock.

As I continued to toss my head back and forth from the pure sexual adrenaline, Andy rose to his knees whilst he continued to fuck me with his fingers.

“Reach into the nightstand beside you, babe. Hand me the lube and a condom you’ll find”

I followed his instructions by turning onto my side; Andy’s fingers hit my prostate as I turned and I cried out in pleasure! I had a great deal of difficulty in wrapping my fingers around the objects since my mind was so out of it with the intense feeling. However, I persevered and finally drew them out and handed them to Andy. His fingers left me and I cried out with the feeling of emptiness. I craved for something to fill me up again!

He assisted me to roll over and placed a couple of pillows under my hips so that my ass was invitingly high. I rested my head and shoulders on a couple of more pillows and, although I felt so open and on display, the level of excitement fought with a serious case of nervous shakes. I heard Andy lube his fingers and a moment later, my frustrations were relieved as his fingers, now fully lubed, reentered my ass.

The coolness of the lube as it hit the heat inside me was a shock and my hard cock flagged somewhat. But, as I Looked back and watched Andy tear of the end of the condom cover with his teeth and throw the foil away, I was entranced as he rolled the condom down the pulsating length of his shaft. I could see through the thin film the veins that carried blood to the ends of that great cock I had learned to love and I was instantly hard all over again. Andy pressed my head to the pillows telling me to try and relax but to tell him if he was hurting me.

I took a deep breath and almost forgot to exhale as Andy reminded me that I had to keep breathing – he wasn’t prepared to lose me yet. Then, I felt the first pressure against my puckered star: I had never experienced such feelings in my life! My lover was going to take my virgin ass after all these years of waiting. Andy gripped my hips and slowly pulled me towards him; he assured me that once he had gained entry he was going to let me set the pace. When I was ready to take more of him, all I had to do was push back a little more. With an audible pop, his domed cock head slipped past the outer tough ring of my ass and I yelped with the sudden pain.

“Do you want me to pull out?” he asked me with concern

“No! Just hold there for a moment; let me get used to the feeling and, WOW! You are so big!”

Andy laughed softly and told me that my ass was so hot and it was all he could do to hold off cumming. With that assurance, I leaned back onto him a little and I could feel another inch or so slip easily into me. The major pain was the first entry but it was really feeling great now! With one motion, I pushed myself backwards until I felt his balls slap against mine and the head of his cock rub my prostate. My cock was jerking under me against the pillows and I could feel my precum flowing constantly.

“Oh, babe! Please fuck me slowly and deeply! It feels so good! I never would have believed …”

My words were cut off as Andy pulled his thinly protected cock almost all the way out and then ever so slowly slid it to the bottom again and again. I was crying out now and felt that I was going to cum at any moment. But there was one more thing to make our first time more memorable; I wanted him to be facing me so we could kiss while we came together.

As soon as I voiced this desire, he slowly pulled out of me (his face was contorted as he tried to control the very strong urge not to cum as the glans was squeezed by my ring as he pulled out). Together, we threw all but two pillows onto the floor; one went under my hips after I had turned over and the other under my head to lift me up. Once I was comfortable – but urging him to hurry – Andy lifted my legs to his shoulders and thus raised my hips to a perfect alignment with his pulsating cock.

Since my ass was already well lubed – both from the AstoGlide and my natural fluids – Andy’s cock slipped easily all the way into me and our balls slapped together once more. When I reached up and wrapped my hands around his neck, Andy dropped his face to mine and we kissed lovingly. With him that close and the different angle, the penetration seemed even deeper and the feeling even more intense. He started to stroke faster and harder as we continued kissing.

I reached between our sweaty bodies to reach for my cock since I was so close to cumming and I wanted to finish myself off at the same time as my love. Andy pushed my hand away as he got to his knees and drawing one of my feet to his mouth, started to suck on my toes. This sent electric shocks through my body since I have always had sensitive feet. With his free hand, he gripped my steel-hard shaft and only had to stroke me twice until I exploded with such force that the thick cum hit my forehead, chin and chest before slowly ebbing. As I came, I started to tightly milk Andy’s cock from deep within and he screamed out as his orgasm hit and I felt him fill the condom!

The swelling of his cock as he came filled me so much and the look of true rapture on his face resulted in me cumming again although no way near the force of the first. However, it was the first time either before or since Andy that I had ever experienced back to back climaxes; and it was wonderful!

Andy collapsed on top of me and, although his cock was still inside me, I could feel it softening. As much as I was going to miss the feeling of that fullness inside me, I knew that there would be many more such experiences for us together.

As his cock plopped free, Andy reached down to remove the condom and drop it in the wastebasket by the side of the bed. He rolled over into my arms and we exchanged kisses for what seemed an eternity. Words of love passed between us until, slowly, we started to drift off to sleep. The last thing my consciousness registered was reaching down to pull the sheet over us and the scent of my lover as I snuggled into his side with my head on his chest. The sound of his steady heartbeat was my lullaby.