Rough young boy gay sex first time Gay Zen State

Rough young boy gay sex first time Gay Zen State
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Hey, it may be an idea to read Confessions from Mac the Flasher A Serial Public Masturbator (2) first as there are numerous references to that chapter in this one. Just so you are not too confused about what ahs happened before. Tenerife 2 My brother Tony and I had spent all day yesterday in various bars and clubs around the town near our hotel.

It was a 14 hour drink fest and my big brother had paid for the lot. I think he felt a bit guilty about leaving me on my own the day before to see his Spanish friends. He didn't need to, as I had a great day at the local nudist beach. (read Confessions from Mac the Flasher A Serial Public Masturbator (2) ). I had woken with furry mouth that matched the feeling of my furry head. I can't remember too much about what happened after it got dark last night and as I stretched and yawned, my arm bumped into some flesh.

There was a brunette still asleep next to me in my bed. She was laying on her stomach and her face buried in the pillow, lightly snoring. A white sheet was draped across the lower halves of our bodies and I lifted it up, we were both naked and I looked at her ass. It was small and very pert and matched perfectly her slim frame. I couldn't remember her name, was it Allison, Abigail?

Something beginning with A I think, but at least she wasn't fat. Checking out my cock, it was still asleep, flaccid across my thigh. But I could see dried cum on it so I must have had a good night. I needed to piss. Dropping the sheet, I tried to gently sit up so I didn't anger the growing headache. I looked over at Tony's bed and saw he was still asleep and on his side, his arm was resting on a pair of tits that belonged to a blonde.

She was on her back and as their sheet was on the floor at the foot of the bed I could see her cunt was smooth and bald, with the unmistakable signs of dried cum on the lips. And like the brunette in my bed she was slim. I may have a full bladder but my cock was paying attention at the sight of her and was waking up. I swung my legs off the bed and stood up. Too quickly as it happened and my headache was now banging a full military tattoo. And I staggered to the bathroom. I turned on the shower to let the water warm up before I got in it and I found the aspirin bottle and swallowed 4 with a long drink of water from a bottle, then I brushed my teeth and got rid of the fur in my nouth.

I checked the water temperature from the shower and stepped in the hot water caressing my tender head. I had forgotten I needed a piss, but I didn't want to get out of the shower so I just pissed where I was.

The bright yellow pee swirling down the drain. 5 minutes later I turned off the water and I felt a lot better, my headache was easing and I felt awake and stepped out of the shower.

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Shit! There were no towels anywhere in the bathroom, then remembered that were hanging over the railing on the balcony. I left the bathroom, I was dripping wet and leaving wet footprints on the tiling floor as I headed to the balcony. Tony and the 2 girls were still asleep and hadn't moved, the blonds' cunt was still on show. Now I had an empty bladder my cock grew hard from the view she gave me. I stood looking at her for a moment, admiring her cunt and my now hard cock was pointing north and I gave it a quick couple of strokes then went to balcony and retrieved a towel.

The morning sun shone brightly on the balcony and as I stood on the balcony, quickly drying my body and as I rubbed my hair dry. The guests from the hotel opposite, no doubt seeing me naked with a towel around my head and my cock was firm and long.

I gave it another few quick pulls and rubbed the head. I may as well give them something worth watching and it felt good. I had finished towelling my head and didn't need to do the rest of me as the sun had finished the job and I re hung the towel over the balcony railing.

Still facing the hotel opposite I gave my cock another few long strokes, then I turned and went inside and filled the kettle and switched it on so I could make some nasty tasting instant coffee.

While I was waiting, I noticed that the brunette had pulled the sheet up and over her shoulders and was now asleep on her side facing me. I couldn't tell before as her head had been buried in the pillow but she was cute in a girl next door type of cute.

My brother had also changed sleeping position and was on his opposite side and facing away from the blonde and was facing the back of the head of the brunette a few feet away. The blonde hadn't moved at all, other than she had spread her legs apart, making a wide upside down V shape which gave me a fuller view of her cunt, and I could now also see her tits as my brothers arm had left her.

They were small, no more than a 34b I'd guess, with small pointy nipples surrounded by areolas no bigger than a 10 pence piece. And even though she was on her back they hadn't flattened out but kept the perfect tit shape. My hand went straight back to my cock and I walked over to the foot of the bed infront of the open patio door and stood over her and I started to wank, taking in the site of her cunt and tits. A mixture of the sight of her nakedness and that I was standing naked infront of the open patio doors so I could be seen by anyone in the opposite hotel made me really horny.

I took long quick strokes of my cock, drinking in the sight of her sweet smooth cunt and I quickly worked myself up to the edge and stopped wanking for a moment. I let go of my cock and as gently as I could I so I wouldn't wake either my brother or the blonde, I bent over her my hands resting on the mattress and I took in the odour of her cunt.

It smelt of cum and pussy juices and I savoured it for a moment. I stood back up and moved around to the side of bed where she was and knelt down on the mattress just at her hip and I stood on my knees so my cock was right over her sweet smelling cunt.

Neither my brother nor the blonde had stirred and I restarted jacking off. I could feel my orgasm building and I pointed my cock at her cunt and I couldn't hold it any longer and I came. I bit my lip so I wouldn't make any orgasm noises. The first hot streak of cum was a bulls eye and splashed right on the top of her cunt and as running down the slit between her cunt lips.

The second hit on the top of her thigh. There was a little dribble of cum hanging from my piss slit, so I moved over to her mouth. Her lips were slightly open, exposing her white teeth behind them. I leant over her head so my cock was just an inch from her mouth and gave my cock a few gentle strokes then pinching my cock just behind the head pushing out my cum into her open mouth, a single drop also landing on her top lip, giving it a shiny sheen I quickly got off the bed and saw the blonde involuntarily lick her lips, the tip of her tongue gently sweeping from side to side a couple of times.

I went back to the kettle and reheated the water and made my coffee, went out to the balcony and sat on a chair next to a small round wooden table.

In the hotel room almost opposite to mine, was a guy in his 20's leaning on his balcony railing, he saw me and gave me a thumbs up sign and I could make out he had a smile on his face. He shouted something at me but I couldn't hear it, but I waved back. He may have seen some of what I had done; I smiled to myself and finished my coffee. At Work 2 It was a Monday morning and I was stuck in the weekly meeting with a handful of others.

The boss was droning on about the same usual crap he usually does at these meetings. I had tuned out his monotonous voice and wondered why he couldn't just send us all an email with all the info he was going over so we wouldn't have these boring meetings. I was sipping my coffee and looking at Jan over the top of my coffee mug, who was sitting opposite me, my co worker who has the office next to mine.

She was looking sexy as fuck, as usual she was wearing a silk blouse, this one was a deep dark blue and clung to her bra covered big tits enhancing their shape. I couldn't see from where I was sitting, but she also had on a tight figure hugging black skirt that stopped 3 or 4 inches above her knees. I know this because I followed her from our offices looking at her ass that swayed from side to side as she walked in her 5 inch stilettos.

I never fail to get a very hard cock when she is around me, today is no exception. Then I was thinking I'm glad he doesn't send us an email and we do have these meetings because then I can drool and slobber when I'm checking out Jan.

I gave my cock a squeeze under the table and tried to move it to a more comfortable position, discreetly of course.

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My boss had said something to me and I nodded in agreement without thinking. My eyes never left Jan, well her tits anyway. I think I saw Jan nodding her head too, but as I said I wasn't really looking at her head. 10 minutes later I was woken out my perving of Jan's tits by my boss.

"Ok so it's settled then, they will both go to Glasgow and meet this new potential client on Tuesday and will probably be gone for the rest of the week.

Tom and Alan, you two will have to take up the slack of them not being here, but I'm sure you can handle it all. OK meeting over guys, back to work" What's going on? Alan was my number 2, it would be fair to say that he carries me along in this job. If it wasn't for Alan, I'm sure I would have been fired a long time ago. "Alan" I whispered. "What's going on, what did I miss?" "You mean what did you miss while you had your eyes glued to Jan's tits" replied Alan, deadpan.

"I'll tell you back in your office in a moment" and turned to Tom and saying something as they left the meeting room together. I nodded a goodbye to my boss and picked up my coffee mug and followed Jan back to our offices. The sway of her ass was as regular as a metronome, a hypnotist could use Jan's butt to help their clients quit smoking. 10 minutes later Alan had told me what I had missed and closed my office door as he left.

I sat there dumbstruck, just staring at the opposite wall. There was a knock at my door, and a few seconds later another one, slightly louder. "Er. yes,come in." I said, quickly picking up a pile of paper, trying to look busy.

Jan entered. "Hey" she said, closing the door behind her. "Do you want to grab some lunch? We can talk about Glasgow." Quickly regaining my composure I replied.

"You bet, Jan. Just give me 10 minutes and we'll go to the Italian place around the corner. They have Chianti to die for." "Great, see you shortly" and turned and left. As you may have guessed, I was going to Glasgow with Jan for 4 days. That is what I was nodding my head to at the meeting. I would be a hotel with Jan for 4 days.

There were a couple of meetings to deal with but I would be in a hotel with Jan for 4 days. I called the Italian restaurant and spoke to Salvo, the owner and confirm he'll keep a table for us and will put a bottle of his superb Chianti on ice and we will see him in about 15 minutes.


I'm feeling like a teenager going on his first date, I'm walking on air. 4 whole days with Jan. Then I'm hit with a memory I'd rather it not be true. She is engaged to be married, and very much in love with him. The bastard. I brush it aside and run off to the toilet, take a piss and get myself together. 15 minutes later we're seated at our table with a glass of chilled Chianti in our hands and Salvo has taken our orders.

Jan is all business, talking about the client and his business and I'm nodding in all the right places and not interrupting. She has it all planned out and her number 2, Tom finishing the presentations we will deliver over the next few days.

"Jan, can I ask a question?" I look at her with a serious face.

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"Sure, what is it? She replies. I take a large sip of the wine and wonder if I'm talking myself out of going to Glasgow with Jan. "Why so you need me to go? You have everything under control and doing all the work, you know the client. Why am I going?" "Are you kidding me? Weren't you there at this morning's meeting? I asked that you come, you know the technical stuff backwards, upside down and back to front.

It took me 10 minutes to convince the boss to let you come. Please don't say you have changed your mind." Jan was very animated during this her reply, her tits bouncing behind the silk.

"No, no of course I've not changed my mind, but you're doing all the work and I'm just there to drink the hotel bar dry. Are we on expenses?" She laughed and had some wine. "This is a very good wine, and to answer your last question, yes we are on expenses, the boss wants us to land this client at any cost, he's worth millions." I met Jan at the airport check in desk at 6 am, dropped our luggage off and got our boarding passes.

Went through security and headed for a coffee shop, I ordered a triple shot cappuccino and Jan just had a black coffee. Less than 2 hours later we were checking in at our hotel and were escorted to our rooms. We agreed to meet in the restaurant for breakfast in 20 minutes.

After dumping my case and suit bag on the bed, I turned on the TV and got undressed and had a shower. 5 minutes later and wrapped in a hotel bathrobe I sit on my bed and open my suitcase pulling out its contents choosing something casual to wear. Our first meeting was to be drinks this evening when the client was due to arrive, so for now I didn't have to dress in a suit and tie.

Still sitting on my bed, my eyes went around the room. It had modern style decor in pale colours. I liked it right away. I then saw the adjoining door to Jan's room, we hadn't requested adjoining rooms but I wasn't going to complain.

I got up and opened the adjoining door on my side and put my ear to her door, I heard movement then another door slamming shut. I ran to my door and through the spy hole I saw Jan walk by on her way to the restaurant no doubt. I checked the time and I still had 10 minutes before the agreed time we were due to meet in the restaurant. I got back to the adjourning doors, reopened mine and took hold of the door handle of Jan's door and twisted it, expecting it to be locked.

It wasn't and opened on well oiled hinges. The layout to Jan's room was the opposite of mine, but in the same pale colours. Her bags were on her bed with some of its contents spilt onto the bed. Typical girls stuff I guess, make up and some clothing. And a plastic bag with a matching scrunched up bra and panties, in white cotton.

I picked the bag up and inhaled the aroma from it. Definitely worn today. I pulled them out, sniffing them to be sure, her panties looked like men's pants but without the Y hole at the front so we could get our cock out for a piss.

I couldn't smell much from her bra, but her panties definitely had a sweaty cunt smell.


I wrapped them around my semi hard cock and began to stroke my cock with them. The cotton felt smooth against my cock and I soon was hard and quickened up the stroking speed. I didn't waste much time and soon cum in them, filling the gusset with my sticky and stringy cum. I cleaned my cock with her panties and replaced them in the bag with her bra and put the bag back where I found it and returned to my room where I got dressed and went downstairs to meet Jan for breakfast.

By 10 am ish, we left the hotel restaurant and went for a walk around Glasgow, a city neither of us had been to before. Let alone Scotland. We spent most of the day getting on buses and just looking around such places as the Argyll Arcade where Jan did some shopping in the jewellery shops, the Bridgetown Cross Umbrella and the Gallery of Modern Art.

We got back to the hotel around 5 and agreed to eat when we were due to meet the client around 8 pm. Jan would let me know exactly when. I got back to my room and chilled out with a few whiskeys from the mini bar and getting naked in my room and watching the Scottish world go by from my room window.

After an hour I took a nap for a while and was woken by a knock from our adjoining doors. Bleary eyed, I put on the bathrobe and open the door. "Hey, oh sorry did I wake you up? In the restaurant for 8pm?" I grunted a reply. "Perhaps I'll knock on your door at 5 to, eh?" I grunted another reply.

"You have an hour." She said and closed her door. I closed my door and fell back onto my bed. I must have dropped off to sleep again as I woke to continuing knocking at the adjourning doors.

Then Jan was shaking me awake. "Get up you lazy fucker, it's quarter to 8 you have 10 minutes" Dragging me up by the lapels of the bathrobe, she pushed me into the bathroom. "Shower, now you fucker" "Ok ok I'm awake" and took off the bathrobe, flashing my ass to a retreating Jan" 5 minutes later and I'm out of the shower and drying myself in the bathroom, fully awake.

The hot water doing its magic. I walk out naked to my room and get dressed in my suit of choice for the evening meal and drinks. No knocking this time, Jan just barges in. "Hey, he lives and breathes, come on let's go. He will be there shortly and leads me out of my room." Jan is wearing a silk dress, with a simple floral pattern.

It hugs all of her curves in the right places, but no bra, or at least it doesn't look like she is wearing one as there is no visible bra line. Black silk stockings and fuck me high heeled shoes. Her arm was looped in mine, yes I had a hard cock. We were seated at our table and told the maitre'd we were expecting 2 more guests, and I ordered a bottle of Australian dry white wine to start with.

After 2 more bottles of the same wine, we guessed the client wasn't going to make an appearance. This was confirmed by the 4th bottle with a message from the front desk. He gave us his apologies, as something had come up he couldn't get away from but would see us at lunch tomorrow. Jan was drunk to say the least. We hadn't eaten as we were waiting got the client to make an appearance before we ordered the food.

And after we finished the 6h bottle Jan thought it best she went to bed. I signed for the bill and helped Jan up from her chair, my arm around her waist and hers around my shoulders. We headed for the lift. Luckily she wasn't heavy, even with her big tits she was slim and not much over 5'5 in height and I could half drag and half carry her into the lift.

She was laughing, a lot and at nothing I could think of, just laughing. The lift pinged open at our floor and we spilled out heading for our rooms. Her room key was in her bad looped over her shoulder, but if I let go of her to get her key from her bag she would have fallen on the floor. So I opened the door to my room and opening the adjoining room doors we headed into her room. Jan was till laughing about something and a few feet into her room she swung around and had both her arms over my shoulders and the side of her head was pressed into my chest.

Her tits were pressed up against me and I decided she wasn't wearing a bra. I pulled her close, my hands on her ass and my cock against her cunt. She looked up at me and kissed me, her tongue deep in my mouth. I pulled her off me. "Jan, Janyou're drunk, very drunk and you have a fiancé, in a few months you are getting married and if you carry on with this you will regret it and the rest of the week will be embarrassing for both of us".

She was still looking at me, albeit through drunk bleary eyes and nodded. I picked her up and carried her to her bed and layed her down on it and I took off her fuck me heels. In seconds she had passed out.

I sat down next to her on her bed, my head was spinning slightly. I went to her bathroom and found some headache pills, I took 2 with a long drink of water from the cold tap and cupped my hands filled them with water and splashed my face and hair, vigorously rubbing the water in.

After drying my face and hair I walk back into Jan's room. She was still gently snoring, her mouth open, her eyes closed. Her silk dress had ridden up her thighs exposing the top of her hold up stockings. I took off my suit jacket and dropped it over the back of a chair and pulled off my tie, placing it on top of my jacket. And walked over to Jan and sat down next to her on her bed. I took hold of both her shoulders and shook her. "JAN, JAN, wake up, wake up!" Nothing, she just continued to snore and sleep.

Letting go of her shoulders I traced my hands down and across the top her chest above her tits, but soon both her tits had in my hands, gently squeezing them through the silk of her dress. I was right she didn't have a bra on. My hands now following the curves of her waist and hips and at the hem of her dress I told 2 handfuls and pushed the top of her dress towards her belly.

The taking the material around her ass I did the same there, pushing it over her ass cheeks.

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As well as no bra, Jan had no panties on either. My god was she going to fuck the client? I don't know, but.


The top of her holdup stockings looked so sexy against her pale skin, the balck silk was sexy. Her cunt was just how I imagined it and just how I like them, shaved and silky smooth.

I bent over her cunt and licked it and took her smell in. She tasted and smelled as I thought she would. I ran a finger up and down her cunt slit, the friction of our skin was pulling and pushing at her cunt lips. I spat at her cunt, and I rubbed the white spit in between her cunt lips, making them feel slick to the touch. My cock was rock hard and straining against my trousers. Pulling my shoes off I then undid my trousers and pulled them down and stepped out of them, followed by my boxer shorts and finally my shirt.

My clothes were a messy pile on the carpet floor. I looked in her bags for any body lotion or face crea and found a bottle of baby lotion in her case. Which I dropped on the bed.

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I went into my room and picked up all 4 pillows that were at the head of my bed and walked back over to Jan. I dropped them on the middle of her bed and then scooped up Jan and turning her over and resting her belly on the pillows, so her ass and cunt was elevated and her dress was up by her tits. I place her head carefully on to her pillows.

I pulled her legs apart, exposing her cunt and ass and picking up the baby lotion, flipping the lid open I squeezed some on to my hand and liberally covered her cunt and ass with baby cream.

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I slipped 2 fingers in to her cunt making sure the cream was deep inside her making her cunt nice and slippery. I squeezed out some more and fingered her ass hole, making sure that was nice and slippery too. Then covered my cock, wanking furiously for a few strokes and getting the cream all over it. Getting on to my knees behind her and holding my cock at Jan's cunt hole I inch forward, my cock getting deeper into her cunt. The baby lotion making it nice and easy. When my cock is balls deep, I start to fuck the still passed out Jan.

No pretence at anything other than my satisfaction. Holding on to her hips I fuck her faster and faster, my cock easily slipping in and out of her cunt. Making sure I have some baby lotion on a finger I ease it in to her ass hole, up to the first knuckle then push it further in to the second and then as far as I can get it in.

Then I finger fuck her ass in time with my fucking of her cunt. I can feel my balls tighten up and feel as if I'm about to cum and pull out of her cunt and take hold of my cock and keep it pointed at her cunt and shoot my load all over it. A river of cum flowing down and getting my pillow soaked. I let out a deep moan as I cum and when I finish I re enter her cunt, enjoying how tight and slippery it feels until my cock goes soft and falls out of Jan's cunt of its own accord. I take my hand and massage my cum in to the skin of Jan's ass cheeks and cunt until it's gone.

I go into the bathroom and take some toilet tissue and wipe any excess away from inside her cunt. Then lifting Jan up off my pillows, I place her back on her bed. Lifting her head and replacing her pillows underneath it and gently placing it down.

I pull her dress back down and smooth it out over her body. Replacing the baby lotion back into her case, I take my pillows and throw them onto my bed. I turn around and pick up all my clothes from the chair and the floor and make sure her room is as it was when we came back from dinner.

I hear a gentle snore from Jan's throat and then go back into my room closing both doors behind me. I grab a quick shower, dry myself slip on my bath robe and then I order coffee for 2 from room service. When it arrives I take it through to Jan's room and place it on the table near her bed.

She is still gently snoring and my hand goes underneath her dress and a give her cunt a 2 finger massage for a moment then replace her dress. I love the smell of pussy on my fingers. I go into her bathroom and turn on the shower, return and pour the coffee into both cups adding sugar to mine. I take Jan's shoulders once more and do a better job of waking her.

"JAN JAN JAN, don't fall asleep. I thought you said you were taking a shower." Shaking her and then repeating the same words a few times.

"Wake up you lazy cow, come on! You even ordered coffee, come on get in the shower." Finally she stirs. "I'm awake, I didn't fall asleep and I'm not a lazy cow." And takes a swipe with her hand at my face.

I pull her off her bed and lead her to the bathroom. "How long has this shower been running?" I ask her. "What? I don't remember turning it on." "Do you remember phoning room service for coffee?" I ask "Oh God no, how much did I have to drink?" "Enough now get in the shower.

I'll be back In 5 minutes" and I close the bathroom door behind me . I pick my coffee up and take a sip. 2 more nights with Jan, they might be interesting.