Str8 Sensitive Guy Gets Explored

It has been a year since that night at the gym. A lot has changed in my life. In finished my courses and graduated. I have a full-time career job with a tax company. I don’t work at the gym anymore, but now I am a paying member. I still live in the same apartment, but now I have enough disposable income to afford my needs easily and save some extra along the way.

With school behind me and just work to fill my days, I find myself with free time on my hands. This is new to me and my evenings and weekends can get lonely. I am 23 now and I it’s time to think about dating. I have only been on a couple of dates in my life, each one with different girls. First dates only, never anything further. The last few years, there had been no time for a social life with full-time work and school.

Now that I have realized that I am gay, I am even more unsure of how to go about meeting someone. There are a couple of good looking guys at my gym. I know nothing about their personalities or their interests. How would I know if they’re open to being with another guy? I am at this new phase of my life but I am inexperienced and clueless.

I made a decision. I pulled out that phone number that I had hidden away a year ago. That number that I didn’t think I would ever call. I still thought about that night at the gym. Honestly, not a single day goes by without thinking about it. I didn’t think I’d ever call this number, but then again something made me hold on to it. Believe it or not I didn’t even know his name. He spent 3 hours that night performing personal acts on me, tickling me, violating me, humiliating me and giving me the most intense sexual release of my life. But I still don’t know his name.

I do know that he asked, practically begged me, to call him sometime. Why not now? I knew he wouldn’t hurt me. He didn’t hurt me that night. In a strange way I kind of feel like he protected me from real harm. Between his bigger partner in crime and their angry boss, things could have gone very differently in a bad way. But he was there and things went his way. Now I found myself dialing his number.

In a gruff, hurried and irritated tone, he answered. I recognized his voice. What do I say? How do I address him? I felt like an idiot. I began, “Uh, hi. This… is uh…”

He cut me off, “I know who this is.” His tone immediately changes. Softened. “I was starting to think you’d never call.” I could hear the big smile on his face as he spoke.

“I…well…I think I want…”  I stammered on.

“You want…”

“I want to see you.”

“I’d be glad to. I am free this weekend. That work for you?” he asked.

I said, “Yes.”

He said, “Where and when Little Dude?”

I knew he knew my name. He knew where I lived. He knew where I worked at the time. He and his cohorts had broken in to my apartment and searched every inch of it. But they never said my nameor each other’s . This one referred to me as “Little Dude” a few times. I responded, “How about Saturday at noon at the coffee shop next to the gym? You remember where the gym…?”

He cut in again, “I remember. I’ll be there.”

I said, “I don’t know your name.”

He chuckled, “My name is Dan. I will see you Saturday, Eric,” and he disconnected the call.

I suddenly felt a wave of fear. What have I done? What if I just re-started something that I would regret? What if this turned out to be dangerous? Torturous? What if I misread this guy, Dan? Was there a way out? Should I just not show up Saturday? No, he probably remembers where my apartment is. Should I call him back and tell him to forget it?

I spent the next few hours thinking, contemplating the situation. I decided that it was time for my life to begin. I had just come to realize a year ago that I am gay. I have now crossed a bridge from one part of my life to another. But I was stuck, just treading water. Not only was I clueless about how to even begin the process of meeting someone, but I also hadn’t even publicly come out as gay yet. I haven’t told my mom or my younger brothers. No one at work knew. Meeting up with Dan would help get me going. I won’t cancel or bail.

Just then my phone pinged - an incoming text. It wasn’t from one of my saved contacts, but I recognized the number from having dialed it earlier. Dan. The message read: “Do you still have those same beat up, smelly old sneakers from last year? Wear them on Saturday.”

I flushed with embarrassment at the memory. Now that I had some disposable income, I had in fact bought myself a long overdue new pair of sneakers. I had not, however, thrown out my old tattered pair. Of course I would do as he said and wear them.

Saturday came and I showed up early at the coffee shop. I hung out on the sidewalk until just before noon and then went in and took a booth. As I sat there waiting for Dan, I thought about what I really wanted to get out this unlikely reconnection. I know he isn’t likely to be a dating or relationship expert, full of advice and tips. I guess I was hoping he could help me with the physical side of my emerging sexuality. I have never been with a man. I have zero experience. A little knowledge and skill would boost my confidence. And Dan would probably enjoy teaching me.

Just then, I saw him come through the door. He looked exactly the same. I had changed a little over the past year. With more time on my hands I was working out more, trading time on the treadmill for time with the weights. I hadn’t transformed into a bodybuilder or anything, but I had added a little toning to my previously little-boy figure. I am 5’ 10” and just about 150 pounds. I recently added an inch to waist going from a 29 to a 30. Would Dan notice the changes? He found me and slid into the booth across from me.

“Little Dude,” he said.

“Hi Dan. You didn’t bring your big friend.”

“Were you hoping I would?” he asked.

“Actually, no. I only wanted you. I just wasn’t sure what to expect.”

The waitress came by and we ordered sandwiches and water. When she walked away, Dan explained, “Steve wouldn’t have been interested in whatever this is. That night last year work to him. He was doing his job…well maybe his job plus a little extra, but it was a job he was paid to do none the less. Whatever this thing now turns out to be, it’s not Steve’s thing.”

So his name is Steve. I said, “Okay, he sure seemed to be enjoying himself that night. At my expense.”

Dan said, “Sure. Work is usually not fun. That night was different. A break from the usual routine. Steve is not gay. My theory is that everyone has at least a little bisexual curiosity in them. You know, varying degrees for each person. Steve dipped a toe in that end of the pool that night. He had fun for a few hours, but he probably hasn’t given that night much thought since. Now me on the other hand? I think about that night every day.”

“I guess that makes sense.”

“Sure it does. Look, I am gay,” Dan continued. “But I find myself attracted to the occasional beautiful woman. Not everything has to have strict boundaries.”

I nodded. In fact from what I remember about my brief time with Dan, he is definitely not one to worry about boundaries.

He asked me, “So what brings us here? Why did you call and what can I do for you?”

The waitress brought our lunches. While we ate, I explained the crossroads my life seemed to be in. How even though I now know who I am, I don’t know what to do or how to proceed. That I have zero experience, and therefore, zero confidence. I told Dan I was hoping he would be willing to help out so I wouldn’t be a clueless idiot when an opportunity arose. I was trying to talk discreetly among the lunchtime crowd, but the couple at the table across from us seemed interest and amused by our conversation.

We finished eating and Dan suddenly got up, crossed to my side of the booth and slid in next to me. He leaned in and said confidentially, “Helping you out with your problem would be my pleasure, literally. Shall we go back to your place and let the lessons begin?”

“O – okay.” I figured there was a chance that Dan would agree and that we would start right away, but I wasn’t sure if, when or how it would happen. But Dan is nothing if not decisive. Now I was getting a little nervous.

He said to me, “Before we go, there’s something you need to show me. I’ve sat here patiently with you for 45 minutes now. You have continued to hide from me what I have been dreaming about seeing again for a year now. Show me the cutest belly button on the planet.”

I reddened a little. “Here? In the coffee shop? How about back at my place?”

Again, Dan had made up his mind. “I need a glimpse to tide over. Just a quick flash and we can go.”

I knew there was no point in further debate. I twisted on the seat toward him, arched my back a little to stretch out the creases and folds from sitting and lifted my shirt. A smile spread across Dan’s face as he took in the sight for the 3 or so seconds I allowed. He commented, “The extra few pounds you’ve put are nicely distributed. I approve and I can’t wait to see more.”

He had only ever seen me the one time and that was for just 3 hours and it was a year ago. Yet still he noticed a difference. Then I remembered that he had been taking photos and video throughout the evening at the gym. He already admitted that he thought about that night every day. He probably saved and viewed those recordings.

I put my shirt back down and noticed the couple across the aisle was enjoying the display as well. Dan said, “Let’s roll.” We got up and as passed the couple, Dan said, “Show’s over folks. Hope you enjoyed it.”

To this point I have spent not more than 4 hours of my life with this man, and yet somehow he has caused me to blush in embarrassment from something he did or said more than anyone else I have ever known. As we crossed the street to my apartment, he led the way. Of course he remembered my building and exactly which apartment was mine.

I unlocked my door and stepped inside. Dan followed closely and closed the door behind him. He wrapped his arms around me from behind and hugged me. His hands found their way under my shirt and he explored my chest and abdomen like a blind man. I sprung goosebumps all over. He spun me around to face him and, without warning, kissed me. His tongue parted my lips, swirled around in my mouth and rubbed against my own tongue. I had never been kissed by another man before and the sensation was amazing. In response I felt a surge in my pants.

We went to the couch and sat. He reached down, grabbed ahold of my left ankle and pulled my foot onto his lap. Seemingly beginning the lessons he said to me, “One thing I like to do is take charge. Be surprising. Don’t just think about doing something. Make it happen.” While he was talking, he removed my shoe and began to rub my foot. He continued, “Foreplay is important. If I remember correctly, stamina is something you need to improve. Foreplay helps.”

I flushed again remembering the humiliation of that night a year ago. He continued to massage my foot. He was not tickling me, like last year. He was making me feel good. I asked him, “Why did you want me to wear the same sneakers?”

He replied, “Your scent was pleasant surprise. When we searched your apartment that night, there was no discernable smell to the shoes we found there. Later when we searched you, these old things were pungent. I know I kidded you about it then, but I liked that ripe, musty scent coming off of your big feet.”

My feet are the only thing about me that is bigger than him. I am an 11 and I think Dan is a little jealous. As we sat on the couch now with one shoe off, I caught a slight whiff of that scent. I don’t get it, but just then he cupped my socked foot by the heel in his palm, raised me up a little and buried his face into the arch, inhaling deeply. I twitched and giggled a little from the sensation. He exhaled inhaled and smiled in pleasure, like he just took a hit off some good weed. Dan pulled my other foot up, slipped off the second shoe and continued the foot rub. I relaxed some, put head back and closed my eyes.

After a few minutes he moved across the couch, hovered above me and kissed me again. This time it lasted longer, we were making out. I was kissing him back, my tongue as active as his. This went on for 20 minutes and he began kissing down my neck. I again sprung goosebumps and he started unbuttoning my shirt. His warm, wet mouth worked its way down my chest and eventually to my navel. He lavished some extra attention there and then he unbuttoned my jeans.

Trying to be a good student I pushed my inhibitions aside and began undoing his pants. We wrestled with each other’s zippers and eventually wormed our way out. He pulled his shirt off in one neat, fluid motion and I ogled his chiseled, lean body. Wow. He couldn’t have had more that 1% body fat. His belly button was an innie too, but not nearly as deep as mine. How could it be with no padding around it? We both had formed tents in our underwear from our erections and quickly discarded those as well.

Now we were both completely naked. This was his second time seeing me naked, but my first seeing him. He was like a Greek god. We knew from last year (they measured me) that I sported a 5.5 inch erect penis. Dan was at least 7 inches. An inch and a half doesn’t actually sound like that much of a difference, but it was much thicker too. Side by side the comparison was comical. I stared in fascination.

He reached out and took my modest member in his hand. I gasped and flinched at the shock of the touch. I reached out and took ahold of him. He barely reacted, though I could feel it pulsating in my hand. We each started stroking and I couldn’t believe this was happening.

Dan told me that we would take turns and he instructed me to lie down. I let go of his throbbing cock and did what I was told. Dan knelt between my legs and began pulling and rubbing on me. He told me to last as long I could. I still had little experience in this arena and I was already feeling close. He worked me like he was kneading pizza dough, his rough manly hands pulling and twisting on my sensitive, virgin shaft. He moved his left hand down to my balls and began to lightly scratch at them. The combination of the two sensations proved to be too much for me and I spurt out my load.

In the end, I lasted more than the 60 seconds I managed last year in the gym, but I still only made it to 2 minutes. Dan said, “We are going to have to work on that. Practice makes perfect.” He wasn’t humiliating me this time around. He was being kind and helpful. My teacher. I used tissues to wipe up my mess.

Dan said, “In addition to learning how to be touched, you need to get comfortable handling your partner as well.” Dan leaned back across the couch and said, “Give it a try.”

He had softened slightly during “my turn”, but I as I began to stroke him he quickly sprang back to full length. He told me, “Think about the most pleasurable parts of the penis. You have the same equipment. You know what feels good.” I started brushing across his mushroom cap at the top of my strokes. He was so big that I was using two hands. He was reacting to the attention I was paying to his sensitive tip.

I still couldn’t believe this was happening. I’d only fantasized about an encounter like this. Now I was living it. After a few more minutes, I used one hand to fondle his balls. He seemed to react positively. With the other hand I gripped the higher half of his shaft and began to massage concentric circles into the sensitive underside just below the head. It took a long time, but in concert with the fondling of his scrotum, those circles got him. His load was bigger than mine and a little got on the couch. He lasted a full 30 minutes. He said to me, “Not bad. As it went on you made some smart adjustments. My endurance time is something you can aspire to.”

We took a break on the couch. I offered him something to eat or drink. We each settled for cold bottles of water. We began to casually chat. It was like we were becoming actual friends. We absentmindedly rubbed each other’s feet and calves while we talked. He asked me, “How often do you jerk off?” Again, blunt and direct.

I answered, “Before last year, not often at all, but since that night, almost every day.”

He followed up, “That’s good. What do you think about when you’re doing it and how long do your sessions last?”

Oh my god. I didn’t want to tell him that what turned me on the most was being humiliated and mocked by him and his friend about how small my penis was compared to their manly members. Instead I told a partial truth, “Basically I think about that night; the first time another man ever touched me and made me cum. As for how long, I guess it depends on my mood? I don’t know. I guess I do it until, you know...”

Dan said, “You need to use that time to work on building stamina. Do you know what edging is? Tease yourself. Get close to climax and back off. Try to last as long as you can. Over time you will last longer and longer.”

I’d never thought of it like that, but it sounded like good advice. I said to him, “Can I ask you a question?”

“Go.”

“That night at the gym, which souvenir did you take?”

Now it was his turn to blush a little. He answered, “I have both of them.” He saw the confusion on my face and continued, “At first, I took your underwear and Steve took a sock. In the car afterwards, I stole the sock from him when he wasn’t paying attention. Like I said before, to him it was just going to something he did in the moment. It wasn’t going to mean anything to him. I am sure he never gave that sock a second thought and never even realized it was missing. For me, I’ll never forget that night. It was more than work to me.”

He seemed to almost get a little misty. He shook it off and announced, “Break’s over. You’ve recovered from round 1. Let’s get back to it.” He lifted my left foot up and began to kiss it up and down the arch. It tickled but not in a tortuous way. He used his tongue all over the top and bottom before sucking each toe individually. Again, I was surprised by the sensation having never felt anything like it before. He moved on to my right foot and performed the same routine before working his way up my legs. He used both his mouth and his hands as he continued higher, past the knees, up the inner thighs. I was tingling and in anticipation, my cock was quickly stiffening.

As he reached his target he surprised me again. He took my entire sack into his mouth. Another first experience me. He sucked my balls and I moaned in pleasure. He was skilled. He knew what he was doing. It would have been easy to have been too rough and turn pleasure into pain, but that didn’t happen. I was taking mental notes and learning from his technique.

After an appropriate amount of time, he assessed my awaiting shaft. At the tip I was moist with precum. He parted his lips and took me in. I threw my head back and gasped involuntarily. It was wet, warm and wonderful. He swallowed my whole length with his lips wrapping around my base. His magical moving tongue was massaging my underside and it was almost too much. He realized I was close again and he eased up. He teased me by sliding his mouth on and off. Then he switched gears and began sucking hard. Another new sensation for me and I lasted only a few more seconds before he sucked down my seed. He reduced the suction but kept at it until I was spent and my convulsions had ceased. I lasted a little longer than earlier, but not by much.

I laid there like a wet rag. It was pure ecstasy, but I was drained. Literally. After catching my breath I understood what the next part of the lesson would be. I had received and now it was time to give. This part was as important as the first part. I wouldn’t want the future me to reach this point and, in that moment, fail or chicken out. I needed this experience. I needed to learn how to give pleasure.

I assumed the position and took him in my mouth. Again, another first for me. He had gone soft while waiting for me to regain my strength. Even soft, he was easily 5 inches but I managed to fit all of him in. I of course realized that the whole time he was blowing me, I never felt his teeth. That was something I would have to work on because despite my conscious efforts, I grazed him a few times and I felt his negative response. As I sucked, he began to grow in my mouth. Once he was fully erect, it was too much for me. If I tried to take in all of him, I would gag.

This was an opportunity. I was not afraid to blow him. I was not grossed out. I wanted to make him cum. I’d never done this before and here I had a willing guinea pig. I repeated the techniques he had used on me as best as I could. After some time and effort, he began to pulsate. I slid up to the spot where my thumb had made those circles earlier and swirled my tongue around the area. His body racked in orgasm and I was proud of myself. Proud both for bringing him to climax and for swallowing his product.

He slowly came down from his high and said, “Not a bad first time effort. And I liked the ending. You got creative. Good job.”

We both got dressed. He kissed me again and said, “I’ll be back tomorrow,” and disappeared out my door.

I stood there for maybe ten minutes. I couldn’t believe the afternoon I had just spent. I was exhausted. I laid down and took a nap.

The next day, Dan showed up as promised. We continued to alternate receiving and giving. He would teach, then I would do. While he was giving me my hand job he was pulling and tugging with such force, I was helpless to hold out much longer than the day before. I was putty in his hands. He got me in 3 minutes. Baby steps.

While performing orally, he introduced another new technique. Instead of taking me in his mouth, he used his lips and tongue, running up and down first the sides of my pole, then the front and finally the sensitive underside. At the top he teased my tip with his slithering tongue. The new technique provided different sensations. My toes curled as I orgasmed after 5 minutes.

We continued on like this for the next 3 weekends. Dan would come over. We would practice foreplay then jump into round one. I would try to last against his handsy efforts as long as I could and in return, I was improving my own skills and trying bring him to climax in less and less time. During round two I made slow progress. I would last just slightly longer each time against that warm, wet, relentless  mouth. I did practice my giving skills and saw greater strides of improvement. I was developing the ability to overcome my gag reflex while learning how to deep throat. I also got better at keeping my teeth out of the way, which is harder to do than I thought it would be.

During the week, I would practice by edging myself as he had instructed me to. It transformed my masturbation sessions from something that needed to be done into something enjoyable and productive.

Over the course of a month, Dan and I had gotten to know each other. I would tell Dan about my job, about growing up, guys at work, guys at the gym, etc. and he would tell me about his life too. We were bonding. We were becoming friends. By the end of that month, I had made enough progress that I had “graduated”. I certainly was no longer inexperienced.

Dan said, “Well Little Dude, I think you’re ready to get out there and begin a real relationship.”

I had grown quite fond of Dan and had looked forward to and enjoyed the time we spent together in these weekend sessions. Was I interested in having a real relationship with him? I asked, “Maybe we could try dating?”

He looked at me and chuckled softly. “What, you and me? That would never work Little Dude. I am almost ten years older than you.”

“But I like you,” I felt like I was 16, trying to convince someone to go to Homecoming with me.

He sighed and replied, “I like you too. I love you. I love you like a little brother. Well, maybe that’s not the best analogy because the things I want to do to you when we are together should never be done between brothers. I feel protective of you. I love you like a friend. You once told me you don’t have any real friends. Let me be your first.”

He saw the disappointed look on my face and continued, “You want to find someone closer to your own age. Someone with more common interests. It could never work between us if for no other reason than because of the choices I’ve made in my life. By the time you’re my age, I could be in prison or dead.”

I said, “Okay, you’re not that old.”

“Not dead from old age. I have chosen a particular line of work. I’m a criminal. Well, my boss certainly is, and I carry out his orders. I do illegal things. You know. You remember the night we met? The things I did that night? One way are another, my days of freedom are numbered. This is why I haven’t had a lasting relationship. It wouldn’t be fair to the other person. You deserve more.”

“But you could quit that business. You could begin a new-“

He stopped me. “I can’t. I’m stuck. I know too much about them and they know too much about me. This is who I am and what I do for as long as I do anything.” He inhaled deeply. “Little Dude, you are important to me. I would like to be your friend. If you need anything, call me. If you find yourself between boyfriends at some point and you want a weekend of no-strings fun, call me. But now it’s time for you to start your life. Get out there, meet someone and be happy.”

“I don’t know where to even begin to look. And it’s even harder being gay. It’s not like people walk around carrying signs.”

Dan said, “You’re overthinking it. Look, you live in the city. There are gay people all around you. Just meet people and see what happens. If you see someone interesting, start a conversation. Go get a beer together. See what happens. Worst case scenario, you make friends. More people in your life to hang out with.”

This sounded like reasonable advice. I said to Dan, “There is one thing I didn’t tell you the truth about.”

He waited.

You asked what I think about when I, you know, pleasure myself. What I said wasn’t a lie, but it wasn’t the whole truth either. What gets me the horniest is thinking about the humiliation from that night. Being a helpless victim, exposed, stared at and made fun of. Having my size compared to yours, a real man, and being ridiculed for being inadequate. I am embarrassed to say that I respond the most to those memories.”

Dan thought for moment then said, “Look. Little Dude. First of all, I already figured as much. The way you physically responded to just our words, it was clear that the humiliation was turning you on, whether you wanted it to or not. We can’t necessarily control our likes and preferences. What I would say is that I wouldn’t share this fetish of yours with anyone too early on. You need to be in a comfortable, safe space with someone before going there. Look at me. I love belly buttons and have a fetish for funky feet. I don’t lead with that when I meet someone.”

He continued, “Secondly, we determined that you are NOT below average. We measured you, remember? You just eked it out. For every dick out there that is bigger than yours, there is one that is smaller. So remember that and don’t let size worry you or stop you. It’s different when guys are with guys. Size just isn’t that important. As a matter of fact, blow jobs are easier to give to and more enjoyable to receive on a smaller penis.”

He went on, “And as far as you finding someone goes, maybe someone will find you. I don’t mean this in a bad way, but you don’t not look gay.”

“What?”

“I mean, look, you’re cute, you’re thin, you’re neat and tidy…you don’t necessarily seem straight. Again, not an insult. But you’re so worried about finding someone, maybe someone will find you. Now get out there.” He gave me one last kiss and while doing so he groped his hands under my shirt and felt around for his prize. He found my belly button and plunged his thumb in. He said, “One last peek,” and lifted my shirt. As he gawked a sad smile spread across his face. “You will make someone very happy. Goodbye Little Dude.” He dropped my shirt, turned and left.

I felt a pang of loss, but at the same time, I knew he was out there. He was there if I needed him.

The next week at work, Paul, one of the newer guys, approached me and asked, “Do you like the Bulls? They’re playing on Friday and I was wondering if you’d want to come over, have a beer and watch the game.”

Paul is a cute, he’s thin, he’s neat and tidy… I replied, “That sounds great. Count me in.”