Category: first times

Willing First Time Submission

The wonderful thing about the internet is that it gives you an anonymous freedom to explore. Lets face it, more people are looking at porn than ever before, because it is accessible form home. I am no different. At 30 year of age I am an average looking guy with a girlfriend who is pretty hot, but very old fashioned. So old fashioned that she does not want to have sex until she is married. So after 3 months of dating my frustration was getting the better of me and having just dropped her at home after a night out, I decided to explore a bit of porn on internet.

After a while of enjoying a few sites I stumbled into a chat room site with various rooms. There was the usual mix of lesbian, teen, amateur type rooms. The one that caught the eye was the one which invited you to find a Master / Mistress. It was perfect I thought to myself. I have been waiting for my girlfriend but she will not let me do anything, here I could go into a room and pretend with someone who was the opposite and just wanted to use me for sex.

The room invited you to leave your inhibitions at the door, so to speak. So what the hell I thought, and in I went! I did not give away much in profile, just stating I was from Sydney and that I was 30 year old and willing to submit. Within moments I had a private message from someone asking if I was prepared to submit, calling me boi. At this point I had no idea if I was talking to a male or female, all I knew was that they were from the US — the mystery was a turn on. So I simply said ‘yes’.

I was asked if I had a webcam? Again the answer was yes. I was ordered to turn it on. I had only ever used my webcam to correspond with last girlfriend who had lived interstate part of the time we were going out. I switched the webcam on. It was strangely arousing to be watched by someone, not knowing anything about them. I liked the lack of control.

For the next few minutes I followed simple instructions to get the position of the camera correct as well as the lights. I was eventually told to strip. What the hell, its not like it was anyone who could recognise me, so I complied. I was getting hard…

After submitting to an inspection of my naked body, I was told that I needed to shave my balls now. I had always been curious about doing that and given that it was summer and getting quite warm, it was the perfect time to shed some fur. I returned from the bathroom with a razor and followed directions to remove all the hair from my balls, but just to trim the hairs above my cock.

When I was finished I was told I was a good boi and that I would be rewarded. But first I was asked some personal questions about what I was looking for and if I was enjoying being a sub. I gave the details I mentioned earlier about my lack of sex life and that yes I was being turned on (though I thought that might have been obvious by increasingly hard cock) and was willing to be owned. I was also asked…

“Do you live alone boi?”

“Yes Sir, I replied.”

“Good boi.”

“Before you get your reward boi, you need to prove your loyalty and give me your address. It is a sign of trust as you know I am not in your country. I do not want to know your real name.” Lots of things went through my head, but my delayed response was clearly annoying the person watching me because I was immediately buzzed. I decided not to think about it and go for the ride, after all they were in a different country and they could not save the webcam broadcast , so there was no way of identifying me. I gave my address. “Now boi, you will get a pair of women’s underwear on and then you will be able to ask me one question as your reward.” I’d never worn it before, but my mindset had became one of compliance now, so I went to my bedroom to retrieve a pair of ex’s panties that she had left behind once.

When I returned to my chair, I was again told I was a good boi and sit there for a few minutes to think about my question — but not to touch myself, which was becoming increasingly harder as I was very horny by now.

After about 10 minutes I was finally given the ok to ask a question.

I asked if the person at the other end would tell me anything about themselves. The reply was swift. “A sub does not need to know anything about their Master other than the fact that I am man in his 40s. You wasted your question boi.”


Massage Parlour Heaven

It was about 3 o’clock on a Thursday afternoon, and everybody was winding down at work. Another long day inside a gray glass and steel skyscraper. My boss stopped by and looked at the paltry pile in my inbox and suggested I take the rest of the day off. Big deal, two extra hours. I had to wait for the train after 5 anyway. Two hours to kill. What to do? I wandered out into the street, slipped into a bookstore for a few minutes and then walked towards the train station. Then I remembered the massage parlor.

For years I had been going to the rub ‘n tugs. I figured it wasn’t really cheating, my wife wouldn’t know the difference and I hadn’t actually had sex. Usually I paid my fee and the girls massaged me and gave me a pretty good handjob but nothing more. Well, occasionally I’d massage their breasts through their flimsy t-shirts and would hold onto their asses as I climaxed, but nothing more. Yes, the parlor would be a good way to kill some time before my train came.

I walked into the parlour and Stacey, who had massaged me in the past, was at the front. “Hi!” she shouted and smiled. “Be with you in a minute,” she said, pointing to the chairs and magazines. She locked the door and disappeared into the back for a few minutes. The doorbell rang and another guy came in. Then another guy. Stacey had her hands full at front. It didn’t look as if they had a full staff, and why would they in the middle of the afternoon.

After a few minutes Stacey waived me down the hallway and followed me into a waiting massage room. I paid my fee then started taking off my clothes as she watched and smiled. Then the doorbell rang again. “Oh damn,” she said. “I can’t believe this. Just a sec.” I finished taking off my clothes and lay down on my stomach on the gurney. I loved the feeling of my naked body on the soft cotton sheets, and looking down through the hole in the table, as I had so often before.

Stacey opened the door after a couple of minutes. “I’m sorry, John,” she said. “It’s just too busy and I can’t get away from the front and none of the other girls are busy. I’m afraid it’s going to be a long wait. I’m really sorry.”

“It’s okay,” I said. “Too bad, I was really horny.” I got up on my side. Stacey looked at my rockhard cock and frowned.

“Wait a minute,” she said and came into the room and closed it behind her. “There is one option, but you might not like it.”

“What is it?”

“Well, we do have one guy on staff who–”

“A guy? Forget it.”

“Are you sure? He gives a good massage and could help you with this little–I mean big–problem,” she said, her cold hand enveloping my veined member.

“I don’t think so,” I said. “I’m not gay.”

“You would hardly know the difference. It’s almost dark in here. I’ll give you a free one next time if you try it out. He’s not making much money except with some of the odd women who walk in here, and I mean odd.”

I sighed. I’d never been with a guy or had really been interested. But I did want to get off. “Maybe he could massage me and then I’ll take care of it myself,” I said.


Vacation At The Beach

Up until now, I have always been a heterosexual male. Recently, though I have been rethinking my sexuality. The last few relationships with girls have been less than exciting and have ended badly. I am not saying that I am giving up entirely on girls, but I am curious about how I would feel about having sex with another man.

So, to explore my newfound curiosity I decided to go on a vacation to an Island resort in Jamaica by myself. However, before going on this vacation, I needed to spend a few extra hours in the gym to whip my body in shape. After all if I was going to attract any attention, I needed to be as fit and trim as I could possible be.

After a month of extra hard workouts, I decided to book my trip. My travel agent was a nice guy, so when I told him that I wanted to go to a secluded beach resort in Jamaica, he said that he had the perfect place. Once the trip was all set, I went shopping for a new bathing suit since all of mine were sort of old and outdated.

I went to this little shop downtown and started looking around at all of the suits. There were hundreds of those surfer-type suits that hang down to your knees and are covered with every color in the rainbow. I didn’t think that style was going to get the reaction that I was looking for, so I ventured into another section that carried men’s thong bathing suits. I was just about to buy a black one, when I spotted a suit rack with what looked like a bunch of strings hanging from it. I thought “what the hell!” if I was going to go down that road, I might as well go all the way. I picked out a bright pink string bikini that was comprised of a piece of cloth no larger than my hand and some strings attached that tied together to hold it in place.

I was almost ready for my trip. On occasion when I have been on a beach before, I had noticed some guys with small rings hanging from their nipples. It really intrigued me and since I have always had naturally larger than normal nipples, I thought that some day I might want to have my nipples pierced. Well, today was that day. I was just in a mood to do a whole bunch of things differently than I have ever done before. Right near the little shop where I just bought my new “bathing suit” was another little shop advertising tattoos and piercing on its front window. So I walked right into the shop.

There was a rough-looking guy at the front desk with tattoos all over his arms and neck that asked if he could help me. I told him that I was considering having my nipples pierced. He said that he had an opening right now if I was interested. I said absolutely and escorted me into a back room. After picking out some jewelry to adorn my nipples, he asked me to remove my shirt and sit back in what looked like a dentist’s chair.

I know that I was in the mood to try new things, but when the moment had arrived I was a little nervous. He marked the sides of both of my nipples with a black marker after cleaning the area to be pierced with an alcohol swab. He then reached over to his tray and grabbed a long needle. He placed the tip of the needle over one of the black markings on my right nipple and told me to brace myself. With one quick motion he pushed the needle right through my nipple. Boy, that hurt like a bitch. Then without wasting anytime, he picked up the 10 gauge nipple ring that I had chosen and inserted it into the hole in my nipple while pulling the needle all the way through.


Glory Hole

God I hate weirdos.

Long-haired weirdos, fast-talking weirdos, salesperson weirdos, gay weirdos. I hate weirdos.

I know, I know, to each his own. But I like good old fashioned values. Mom, apple pie, Old Glory and, as we used to say in the Army, the girl you left behind.

Well, I have to admit, in the spirit of full disclosure, that I have a few vices. There’s the occasional belt of straight up Jim Beam, there’s a penchant for fast cars which like to exceed the speed limit, and shaving a few strokes off my golf score. Oh, another vice came to the front by accident, when I attended a bachelor party which started at a strip club, moved over to an adult boutique, and then back to the club for a few lap dances.

So what, you say? No real harm there, right?

Probably not. Still, the latter trip to the world of exotic dancing and peep shows wet my appetite, and on a business trip to Philadelphia I found myself drawn, like metal to a magnet, to the flashing neon lights of an adult bookstore on Market Street.

Now I have to tell you that I’ve had a fairly normal sex life, at least to my knowledge. I like making love to a woman, caressing a soft body, hearing a woman moan to my ministrations. Of the dozens of positions explained in the Kama Sutra, though, I still liked missionary the best, although I have never tossed a young lady out of bed if she wanted to be on top or do the deed doggie or side-by-side. What can I say, missionary is my favorite, and I am not ashamed to admit it.

While I may not have the most active sex life, it is fulfilling. I’d like it to be more frequent, but, I can’t complain.

Still, when looking out the hotel window, that adult bookstore beckoned and I found myself casually walking over to it late one Tuesday night. My work was done after a productive business dinner, and I was catching the morning Metroliner back to the Big Apple.

As I approached the store I noticed a couple guys leaving, and since they looked “normal” I felt a boost of confidence, as if I wouldn’t be, well, a weirdo, for entering. Armed with that evidence I opened the door and stepped inside. There were magazines, videos, lingerie, adult toys, you name it. But what drew my attention was the wall filled with movie boxes depicting the clips being showed in the peep shows in the back room.

Wow, everything was on that wall, from straight to gay, from domination to transsexual, you name it, and it was there. I quickly looked around, then slipped back into the dark room with about two dozen booths. I went toward the back and slipped inside a booth in the back, making sure I closed, and locked, the door behind me.

That was my first mistake, because the room was totally dark. Damn, I thought, there must be a place to drop some quarters somewhere. After feeling around like a blind man, I finally found a place to drop my change, and dropped in a couple quarters, immediately starting a film.

With the start of the show there was light, and I immediately saw a place to deposit a bill, and added a fiver to my change. Then I settled back against the wall to watch the show. On the screen was a woman being mauled by a man with a huge penis. He was banging her and she was moaning in feigned ecstasy. I noticed a button, touched it, and immediately the view changed to a pair of men making it with each other…disgusting.

On to a blowjob which kept me spellbound, hardening my cock in my briefs. That feeling forced me to unhook my pants and unveil my cock to the dark booth. I slowly stroked it, watching the blonde suck the large cock, which ultimately erupted in her mouth. It was awesome. I especially like how she swirled the cum around in her mouth.

Another click and I saw a woman being gang-banged, while another click saw a young cheerleader being screwed in a locker room.

It was about that time when I heard a sound toward my right. I glanced down, and stepped back as, from the wall, a finger was sliding around a hole in the wall. At first I couldn’t believe it, but then I quickly came to the realization that these booths were sometime more than a place to watch porno, but a place for gays to have some sort of faceless rendezvous.

Unbelievable!


Getting a Workout

My girlfriend gave me a membership to a gym for my birthday. I didn’t really need to lose weight, just tone my body back up again and get some good muscle definition.

I went to the gym and used some of the equipment that I was familiar with and was working up a sweat getting back into a routine. I noticed some new equipment and went to the front desk to ask if I could get some instruction. The girl at the desk told me that my new membership included instruction from a personal trainer at no charge for the first thirty days. We discussed the details and I signed up to start with a trainer the following week.

I made my appointment for late in the evening so I could come in after work. I met Antonio, my trainer, the first night. He was a very fit guy that most women would drool over. He was in his early 30s, average height and Latin.

Antonio showed me the equipment that I was not familiar with and explained how to use it. We discussed which areas of my body I wanted to target. I told him I felt I needed to work on my legs, butt and abs. He looked me over and I felt self conscious under his gaze, but at the same time his eyes ignited me like a fire. He told me that to record my progress we were going to take starting measurements and then do weekly updates. He pulled out a tape measure and proceeded to measure different parts of my body. His hands grazed me from time to time and I was working to keep my breath steady. As he parted my legs and wrapped the tape measure around each of my thighs to get the measurements I hoped he couldn’t tell that I was getting hard when he touched me. I didn’t know why. I had never been into guys, but it happened that night. He put the tape measure away and I was relieved that the torture of him touching me was over while at the same time I wanted him to keep touching me.

In the following weeks I worked hard and was seeing progress in the shape of my body. I was starting to feel more comfortable with how I looked and was starting to buy new clothes

One night Antonio and I were going through our normal routine. I was sitting on a weight machine and doing some rows when Antonio sat down behind me and placed his arms over mine. He told me that I needed to adjust my form to get better results. He pulled along with my pulls and his arms remained on mine as we let the weights gently slide back. After a few repetitions he placed one hand on my rib cage and told me that I needed to breathe through each repetition. I could barely breathe with his hands on me. The sensation was unfamiliar. His hand was just inches above my cock and I wanted him to reach down and touch me.


First Time Sucking a Big Black Cock

To my great surprise I am obsessed with sucking cocks, especially big black cocks. Well, sucking one particular big black cock.

I am ‘straight’, dating and fucking only women for most of my life. I was good at that, finding willing female partners an easy thing. I had experimented with men, but it was mostly just mutual jack-off sessions.

I work for a very large accounting firm in a semi-supervisory position. I was the guy that ‘checked on the checkers’. I would travel from audit site to audit site, reviewing the work of others. It was on one trip to Portland, Oregon that I became aware of my obsession.

I had flown in the prior evening, First Class of course. The audit was in progress and I was to meet the audit team that morning. I showered, closely shaved, lightly applied a very expensive men’s cologne and dressed in my best ‘power suit’. I always wanted to make a strong first impression on these things.

I am fairly tall, around 6’3″. I keep in shape spending at least three days a week at any gym I can find. I have dark hair and eyes, my skin olive. I have to shave often, sometimes twice a day. Surprisingly I do not have an excessive amount of body hair. I’m considered to be ‘classically handsome’. My name is Kurt.

I met with the team. I knew by our company standards that all of them would be bright, hard-working individuals. One person stood out among the others; a very handsome, very athletic looking black man. His name was Marcus.

I spent the day speaking to each individual auditor; reviewing their respective work. The ‘interviews’ were done one-on-one. It was Marcus’ turn. I greeted him, shaking his firm large warm hand. We spoke of audit items. His work was perfect and I told him so. As he was my last auditor, and the day was ending, we began to speak of more personal things.

I asked him about the nightlife in Portland. He said, “It can be fun, but it’s really up to the individual.”

“Would you consider showing me around?” I asked.

He thought for a moment then answered, “Yes, but I wouldn’t want anyone else to know, that might cause some problems in the office.”

“I agree.”

“I can pick you up this evening, are you at the usual hotel?” he said.

“Yes,” I answered.

“Would you like dinner, or something a little more fun?” he asked.

“A ‘little more fun’ please.”

“Good, I’ll pick you up at ten, in the lobby, dress casual.”

I returned to my hotel and awaited the ‘appointment’. It seemed far away. I showered and shaved … again. I dressed in clean expensive casual clothing. I reviewed myself in the mirror; ‘not bad I thought’. Sometimes I can be a little vain.

I went to the lobby. Marcus was already waiting. We greeted, both of us smiling. It was obvious the pressure of the review was no longer present. He directed me to his car, a very nice black Mercedes.

In the car he said, “This might end up being a fun night. I do have to tell you that I’m gay; are you OK with that?”


Boys Will Be Boys

Scott was so excited, he had just gotten his first apartment. He didn’t really have any special plans or anything, so he called his best friend Matt to come over. Matt brought some smoke, and a 12 pack of beer. They had been best friends for many many years, and they were very comfortable and relaxed around each other.

They were both very buzzed quickly, and as they sat watching TV, and talking Scott suggested they watch a new porno tape he had just purchased. Matt giggled, and agreed that it would be fun so they put the movie in the VCR, and sat quietly drinking while the movie started.

It was basically a 2 and 1/2 hour collection of blow jobs and cum shots, so the action began right away. As Scott watched the first suck scene, it began to turn him on. His cock began to grow, and it bulged out very noticeably against his tight gym shorts. He felt very nervous and uncomfortable about it, but as his eyes wandered, he noticed that Matt also had a raging hardon which looked as if it were ripping the seams out of his shorts. Matt’s eyes met Scott’s, and he quickly looked down at Scott’s crotch. “Looks like we have a problem,” he said laughing loudly. Scott wanted to jack him self off so badly, but didn’t know how Matt would react. Matt broke the ice finally, by stroking himself through his shorts. His hand moved up and down his stiff cock as it pressed tightly against his shorts.

Scott felt braver now, and decided to go a step further than Matt. Scott stood from the couch, and lowered and removed his shorts. His 7 and 1/2 inch cock sprang forth slapping loudly against his belly. Matt looked at Scott’s stiff cock and stared at it intently. Scott began to stroke himself, moving his fist up and down his cock. His cock throbbed and pulsated wildly as his hand moved up and down the thick shaft. Matt quickly stripped, and his cock was larger than Scott’s. Scott’s eyes opened widely as he caught his first sight of his friends massive erection. It was a bit over 9 inches long and very thick.

There wasn’t much hair around his cock, and his large balls looked hairless. Scott had never thought about his friend in a sexual manner before, but he suddenly felt a desire to suck his friend’s impressive boner. Matt sat down next to Scott on the couch, and began to stroke himself. The 2 men sat next to one another frantically masturbating themselves. Their eyes remained glued on each other’s stiff cocks. Scott pressed his thigh against Matt’s and softly slid his leg back and forth. The skin contact really turned both of them on. Matt’s large cock began oozing precum, and he quickly wiped it away with his fingers.


Oral in the Theater

My day off and I have woken up horny as hell with a raging hard on, there is noting unusual about that I love to have morning sex or if I wake alone then a morning masturbation session. I started to stroke my cock , I like a soft grip and slow stroking motion love to feel the smooth warm skin of my cock while I move my hand up and down the shaft.

I started to drift into fantasy mode where I was imagining this girl I know was sucking my cock this was getting me extremely hard, my heart rate quickened while I tried to maintain a nice even slow pump of my hand up and down the full length of my now fully erect cock which is rock hard at 7 and ½ inches.

After about 15min Pre cum started to ooze out and I stopped pumping and grabbed firmly at the base of my cock and squeezed hard milking from bottom to top to get all the pre cum hmmm how I love pre cum I then catch the whole blob of pre cum on my index finger and place on my tongue hmm Fuck that is nice and then resume back to the slow full stroke with a light grip on my cock again.

After repeating this process for another 15 min I was ready to cum but I like to prolong as long as I can because I love the feeling and don’t want it to end so I stop and get out of bed still naked and go and get some breakfast (living alone means I am naked most of the time when at home) while getting something to eat and making a coffee pre cum is still dripping out and I continue to not let it be wasted so I ensure I get it and rub on my lips.

I grabbed one of my many porn DVD’s and put one on getting ready to finish what I started when I woke today, I was extra horny and starting thinking about going into the CBD to where I know are a few adult shops that have cinemas in them and watch some porn on the big screen, I had the day off work so I thought fuck it I am going to go and masturbate in the adult theater which I have done before even though there was only a few guys in there I positioned myself in a dark corner and I know they couldn’t see me but it still turned me on knowing that someone else knew I was masturbating in the same room. So I got dressed and jumped on a train and headed for my day of self gratification.

When I got there my heart rate was already higher due to the anticipation of what was about to happen I paid my $10 and the attendant buzzed the door and I entered the theatre stood just inside the entrance and waiting for my eyes to adjust while I watched a close up on the screen if a lovely shaved cunt being penetrated by two cocks, once I could see better I looked around so a seat and was surprised to see around 4 others already in the theater. 2 of which were openly stroking their cocks.

I found a seat second row from the back left hand side of the theater and sat third seat in from the isle this meant it was light enough to be seen but far enough away to not feel like a pervert. I was watching the porn and had a ragging hard on but was a little embarrassed to pull my cock out but I was getting to the point where I had to feel it as I was to horny so I tried to quietly undo my zipper on my jeans and and let my cock spring free, I still remember the feeling of it feeling the cooler air from the air-conditioning and that first touch of my hand it felt great, I looked around and tried to see if anyone was looking and then I started my light slow pumping from base to tip of my cock and was thinking how great this felt being in the same room as others stroking my cock knowing that they knew I was stroking it.


First Time Gay Oral Slut

Hi everyone. I’ve been reading these hot stories for some time so I figured I should post one myself. This story is true and still turns me on today. I hope it reads well I never wrote a story before.

When I was 20, I was in my third year at college in the City of Boston. One day I decided to check out this piano store near my school. I was talking to an older man who worked there and I could tell was gay. I started to flirt with him and found myself extremely turned on by the thought of acting like such a slut. I have always had an urge to suck some cock but to this point I have only jerked off 2 other men in my whole life.

I asked him if they offered any lessons? He gave me the usually answerer, but I didn’t want to really learn so I asked him if “he offered any private lesson” with a devious smile on my face. He got excited and offered me his email and said to write; and with that he left. I was unsure if he got the hint but I know my cock sure did.

After a few emails with not much going on I decided I didn’t want to wait any longer. So the next email I told him “I would love to CUM over and have to teach me something new.” Again I couldn’t believe how much of a slut I was becoming and moreover, how much I loved it.

To make a long story shorter about a week later I found myself knocking on this strange man’s door waiting for my life to change. He opened the door with a big smile and welcomed me inside. By this point I should tell you this man was about 50 years old. He had a cool townhouse condo in the middle of the city and led me downstairs. We began to talk about this and that and I was really really nervous because he was only the third man I was going to tell my dirty little secretes; that I liked men and more to the point that I liked to please men.

He finally asked me why I was there and I answered “you know why.”

He said “no I don’t tell me.”

So I said “I want to try stuff with men.”


Australian Lifeguard Lover

I was lying on a beach in Australia, enjoying the sunshine, when suddenly a lifeguard rushed past me. Even in those brief few seconds that he was in view I couldn’t help but notice that he was incredibly hot.

I turned around to see what had got him in such a hurry and saw him ticking off someone that had trespassed where they should not have. What I saw was an incredibly shapely, full masculine ass underneath that sexy red swimsuit that he wore. Fortunately his swimsuit was not too tight so the material followed the natural curves of his man melons instead of cutting across them. He had a pair of mighty fine legs that were covered in long, silky blondish brown hair.

Having delivered his lecture he turned around and started making his way back to his post. I stole a quick glance and noticed a deliciously full package nestled between his thighs. A trail of dark brown hair led out of his swimsuit and disappeared under the cropped vest that he wore. He had powerful shoulders and a well developed chest and washboard flat stomach. He was just one of the hottest men I had ever seen.

So imagine my surprise when he stopped near me.

‘Sorry about that. I hope I didn’t kick sand in your face as I went by.’ he said.

I was dumb struck and couldn’t think of anything to say so I just smiled at him.

‘It’s a beautiful day for it, isn’t it?’ he said.

A beautiful day for what I wondered. I knew what I would like it to a beautiful day for – covering his sexy body in hungry kisses. But I figured there was no chance of that.

‘It’s a pity you have to work.’ I said.

‘I’ve just finished my shift.’ he replied as he sat down on my towel uninvited, not that I minded.

He was quite easy to talk to but I was extremely self conscious of being naked while he was clothed. Each time he flashed me that brilliant white toothed smile of his I felt my lust rise higher. My heart seemed to be beating faster than normal and I felt my throat and tongue go dry. It had been a long time since I felt so turned on. And then when he slipped a hand up his vest and idly brushed it against his left nipple my cock rose of his own accord.