Learning with Jon

How a guy from work finally got my sex life started.

It was early 1980's and i had just started working as a van driver / stores man in a clothing wholesale company. it was only a small company with mostly old guys, who didn't really like me for simply because I was 20 years old.

One other guy was Jon. He was mid 40's, far too intelligent for the job but was rebuilding his life following a messy divorce. We got on ok as work mates but wouldn't say we had much in common, but at least he made an effort to talk to me.

I don't even recall how we got onto the subject of chess but Jon asked if I played, to which I said I knew how to but never really had the chance to play against anyone.

That lunchtime he said "Come on lets go play chess."

I looked at him puzzled and he explained that he lived literally 2 mins away from work, which explained where he went every lunchtime The lunchtime chess became a routine for the next couple of weeks until one day when everything changed.

Jon said his mate had lent him a porno ( straight porn) and did I want to have a look. We only watched about 15 minutes as we had to go back to work but I couldn't believe how aroused it got me.

I'd never seen a porno before as I lived at home with mum and 3 sisters, so never had any time alone. I ended up having a wank in the toilets back at work.

Next few days i never saw Jon as i was out on deliveries but next time I was around we went to his as usual. I was already starting to get hard when we arrived at his house with the expectation of watching porn again.

Jon made coffee and then put the porn on. We sat at opposite ends of the sofa, my cock was rock hard but was being restricted by my pants and jeans and i was relieved when Jon got up and went to the kitchen, giving me the chance to adjust myself and at least get my cock in a comfortable position without him seeing me.

The scene we were watching ended and the next scene started up, which was lesbian porn. Id been watching for about ten minutes, when I felt my cock starting to twitch and I started to cum in my pants.

I didn't have a full orgasm but released enough cum to create an embarrassing wet patch on the front of my jeans. Jon obviously saw this and said I'd better go and clean myself up.

Blushing bright red, i got up and went to the bathroom. I stood looking in the mirror not really knowing what to do for a moment, before taking off my jeans and dabbling the wet patch with a towel. Next I looked inside my pants at the sticky mess I had made and also realised I was still hard.

I took of my pants and run them under the tap. The next moment the door opened and Jon walked in.

Instinctively i covered my hard cock with my hands but Jon seemed nonchalant about it and came and stood behind me. Next few seconds I felt his arms around my waist and he whispered into my ear

" Don't worry, it's ok."

I looked into the mirror and could see Jon smiling back at me and then felt his hand gently squeezing my cock.

I was frozen in the moment as he repeatedly squeezed and released me and then began to slowly wank me. Jon pressed up tighter against me and then after no more than 6 or 7 strokes, my cock twitched again and I shot my load.

Jon still had one arm wrapped around my waist and the other hand was still holding onto my cock and whispered into my ear

" I hope you don't cum that fast when your girlfriend wanks you?"

The blushing returned and after a few moments of silence I responded and said

"I've never had a girlfriend,that was the first time I've ever been wanked off."

Jon shook his head in disbelief at first but then realised that i was stating a true fact.

"Well did you like it?" He replied

My head was spinning, I'd just had my first ever sexual experience but it was with a man, did that mean I was a poof ( I think that was one of the general terms in those days).

" We can do it again next time if you want to?" He asked

I just looked in the mirror at Jon and said "Ok."

"You better clean yourself up, We've got to go back to work/"

He gave me a pair of underpants to wear as mine were full of cum and soaking wet from where I had tried to clean them. The rest of the afternoon was a blur as I constantly replayed in my mind what had just happened.

All weekend, it was all I thought about. Had I enjoyed what Jon had done to me? Did I want him to do it again? As I lay in my bed that Saturday evening, wanking off, the answer became clear. That answer was a resounding Yes.

I told myself that I deserved to have a sex life, all my mates were sexually active or claimed to be so why shouldn't I. It would only be for a short while until I got a girlfriend (that was highly unlikely as i was too shy and nervous to even try and speak to girls) It didn't mean I was a poof.

The working week began again. To my disappointment, I had deliveries to make and was out all day. I thought about Jon's offer all day whilst out on the road and by the end of the day I had back tracked on my earlier decision and there was no way it was happening again.

Tuesday at work, Jon acted as if nothing had happened the previous Friday and I was relieved that he hadn't mentioned anything.

Lunchtime arrived and Jon casually walked by me and said " Coming round?"

All I had to do was say No, I wanted to say No, I should say No but i thought back to last Friday and my cock stirred. Instead I just nodded at him and put my coat on. The short walk to Jon's was quickly over and we went inside.

"Do you want the porn on?" Jon asked

"Yes pleas," I replied

The porn started and as expected I got hard. After a few minutes Jon asked

"Do you want to take your jeans off in case you have another accident."

It was embarrassing to be asked that but the fact was it was a possibility so I removed my jeans and sat there in my pants, obviously fully aroused and with a little damp patch appearing where my precum had started to leak.

As was the norm, we sat at opposite ends of the sofa, however Jon got up and picked up my jeans, folded them neatly on a chair and then sat back down next to me. He smiled at me and placed his hand on the bulge in my pants, we just sat watching a hot blonde getting banged by a muscle bound hunk.

We sat like this for about 5 minutes, long enough for the hunky guy to finish shagging the blonde and then Jon asked

"Do you want to take your pants off?"

Again the doubts came flooding back but this was also matched by the desire to be wanked off and I stood up and took them off and sat back down next to him. Jon's hand gently rested on my cock again

"I'm going to slowly wank you and if you think you're going to cum say stop," Jon said.

He gave me a couple of strokes and i immediately cried out "Stop,stop."

He removed his hand for about a minute and then started again,

"Stop, stop," I said again for a second time after about thirty seconds of being wanked. Jon paused for a bit we before starting again.

"Stop, Stop I'm gonna cum."

This time Jon just carried on wanking and then suddenly stopped just about as I was about to cum. The sensation was different. I cum but didn't get the orgasm feeling.

i didn't know this at the time but Jon had just given me my first ruined orgasm.

Jon told me to go and clean up. In the bathroom I felt confused, id cum but hadn't really felt anything and I was still fairly hard. I cleaned myself and went back into the living room, still naked from the waist down.

Jon had moved position and was now sitting full length on the sofa, he opened his legs and said to sit between them. I felt his arm around me again and back on my cock, slowly wanking me.

"Shall I say when to stop again," I asked

"No just relax and enjoy." was the reply

Jon slowly wanked me until my breathing became to heavier and I guess he sensed i was getting closer and he started to speed up the strokes as i let out a huge groan and shot a huge load over his hand and onto my tee shirt.

"How was that?" Jon asked

I never answered, the massive grin and smile told him all he needed to know.

The next few weeks became one giant wank fest. Jon was wanking me off or I was wanking in front of Jon 2 or 3 times every lunchtime ( fortunately we used to get 1 1/2 hours for lunch).

After another Friday lunchtime wank, Jon asked me if I wanted to come round on Saturday and watch a video he had rented. I wanted to but was also supposed to going watch football with my mates and said I'd try and get back.

I went to the football, and normally I would have stayed out drinking but I made excuses that I didn't feel well and when we got back i told my mates i was going home rather than up town.

I made sure they were out of site, found a phone box and called Jon and asked if I could still come round. He, of course said yes and I walked from the train station to his, arriving about 8:30.

Jon gave me some money on arrival and asked me to go to the Chinese just down the road from his. We ate the food and Jon opened a bottle of wine. I wasn't really a wine drinker but drank it anyway and Jon put on the video.

I was expecting porn but it turned out to be a comedy. We got through two bottles of wine and whilst I enjoyed the film, I was constantly thinking when is he going to wank me off.

Jon left the room and returned a few minutes later in just a dressing gown. This was something new, all the previous times with Jon, I had been naked or naked from waist down whilst he had remained fully clothed. He took my hand a led me to his bedroom. He undressed me, which he had done many times previously and he took off his dressing gown.

This was the first time I'd ever seen anyone naked in a sexual environment, only other times being the changing after playing football on Sunday mornings which definitely didn't count as sexual.

I stood mesmerised as Jon's cock grew hard (7 1/2 inches)) and thought how much bigger it was than mine.. Jon got onto the bed and gestured for me to join him.

I felt his hand on my cock and then Jon moved position and i felt his tongue licking up and down my shaft, before taking my cock in his mouth. Wow this felt unbelievable,

I'd never imagined my first blow job would be from a mid forties man but it was. With all the previous wanking by Jon and the wine that Id drunk I was learning to control the urge to cum but I knew I was getting close.

In all the porn Id watched, the guys had always cum on the girls faces and thought that would be what Jon wanted. I told him I cumming but he just kept on sucking and I exploded in his mouth.

Jon kept sucking and then began to lick the last drops of cum from the end of my cock. That post orgasm sensation and sensitivity was unbelievable and I've never forgotten that moment.

Jon repositioned himself next to me and put his arms around me and began to cuddle me. I looked down and could see Jon's rock hard cock pressing into my leg, he then moved in and passionately started to kiss me.

I temporarily froze, again kissing was something I'd never done either with anyone previously but then I just responded and our mouths became locked together as we explored each other with our tongues.We finally broke off our kiss.

"Did you enjoyed your first blow job?" He asked

I replied laughing "What do you think."

He replied "Well would you like to suck me?"

At this point I knew a line had been crossed and moved position and took my first tentative suck on a guys cock. Jon was pre-cumming and i was surprised to find it tasted similar to mine.

I tried to remember what Jon had done to me and licked the shaft and balls before becoming more adventurous and started to take his whole cock in my mouth, gagging frequently as i did so.

After a bit we changed positions. Jon stood up and i kneeled in front of him. Jon put his hands on my head and began to fuck my mouth only stopping when i was gagging too much.

We changed positions again, Jon lay on his back on the bed and i started to suck him again but he manoeuvred me into a 69 position with me on top.

Obviously by now i was rock hard again and felt Jons mouth around my cock again. This spurred me on as i sucked wildly on his cock. Jon groaned and shot his load into my mouth.

I wasn't sure what to do, I swallowed some although this was unintentional as the rest run out my mouth and down my chin and neck. Jon wriggled free from me and lay beside me and began kissing me again and said that I'd done good for my first blow job.

He went and fetched a face cloth and cleaned me up. I was still hard. Jon got under the duvet cover and beckoned me to lay next to him. I cozied up as Jon wrapped one arm around me and with his other took hold of my cock and began to wank me until i cum.

Jon saw me looking at the clock on the beside table, it was just gone midnight and said "Why don't you stay the night."

I feel asleep cuddling up to Jon and woke up alone in the bed in the morning with a hard on, but also felt ashamed about the previous night and that I had sucked another man's cock.

What would happen if my mates found out. I kept telling myself I wasn't a poof but couldn't deny I'd been doing poof things for the last 6 weeks now. I needed to find a girlfriend and put a stop to this.

Jon must have heard me stirring and shouted out did I want a coffee. A couple of minutes later Jon appeared bedside with a coffee for me. He was also still naked. He placed the coffee on the bedside table.

"Are you ok?" He asked

I think he could see in my face the turmoil going through my head at that moment.

" Everything's ok. it's your life and you can do whatever you want," He added

At that moment, I wanted a girlfriend, I didn't want to be a poof but I wanted Jon to wank me off again and I wanted to suck Jon's cock again. I reached out and took his cock in my hand.

"Are you sure?" He asked

Was I?, probably not but I was horny and threw back the bedcovers to once again reveal my hard cock to him. He smiled and his cock began to grow.

" i want to suck your cock again" I said.

He leapt onto the bed and I started giving the second blow job of my life.

Jon was a lot more verbal this time, encouraging me to suck him and play with his balls and the dirty talk turned me on even more. Jon eventually shot his load, again I swallowed some and dribbled the rest down my chin.

I immediately started to wank myself off and quickly cum on myself only for Jon to quickly lick it clean from my stomach and still hard cock.

Eventually we got dressed and I left to go home. Jon said he had a few days off the next week and he'd see me on Thursday.

The next three days I again thought long and hard about what I was doing with Jon, however this time things were different. I liked being wanked off by Jon and I wanted to suck his cock again. I didn't need to tell anyone about it, I was just going to carry on, any girl friend ideas could wait.

Thursday and the Friday I was on deliveries so didn't see much of Jon. Last thing on the Friday he asked if I wanted to come round again on Saturday. My cock stirred and I said Yes

I arrived at Jons on sat evening and we immediately began kissing. I shocked myself by how eagerly I responded and how passionately I kissed him back.

"I've got a surprise for you in the bedroom," Jon said.

I nervously made my way to the room. All sorts of thoughts were going through my mind, was I being set up, were there other guys in there? I opened the door, there was no one else there, just a box on the bed.

I opened the box and knew instantly where the contents had come from. Jon had " borrowed " them from work. Knickers, stockings, suspender belt and garters all in white.

"I want us to fuck tonight " he said " I'd love it if you would wear them for me".

The first thoughts that ran through my head weren't does he want to fuck me or me fuck him but whether or not I should wear the clothes. I had pretty much accepted that i was happy with my sexual activity with Jon but dressing as a woman?? fucking hell, that was a bit weird.

Jon again asked

"Do you want to fuck?"

"I'm not sure " I replied, still not really thinking about whether I would be fucking or getting fucked.

"Shall we have a shower together then and we can talk about it afterwards," Jon suggested

The thought of showering with Jon turned me and I quickly stripped off, instantly revealing my erect cock, Jon followed suit and we got into the hot shower.

He lathered up a sponge and began washing me, firstly my back and chest before moving onto my cock and balls. Then he began to wash my arse cheeks, with his bare hands and began sliding his finger up and down my arse crack, occasionally touching my hole.

The penny dropped and I realised that he wanted to fuck me. He was standing behind me wanking me and I felt him rub his now hard cock up and down my cheeks. The wanking had got me close.

"Make me cum Jon "

He rubbed my hole with his finger on one hand and wanked me with his other and i quickly shot my load.

He washed me clean again and said shall we talk? We dried off and put on dressing gowns and sat on the sofa and put some porn on the tv and opened a bottle of wine.

I had lots of questions for Jon,

"Will it hurt?" and " Will you stop if I don't like it?" being the main ones/ Jon did his best to reassure me and with passing of time, porn on the tv and the wine, I was starting to feel horny again.

"OK let's try it and see how it goes," I finally agreed

"Will you wear the clothes for me?, It would be so sexy with you in virginal white."

I think I'd reached the point where I didn't care anymore and just said "OK"

I went off to his bedroom and began to put on the stockings, knickers etc. I have to confess, it did turn me on and my cock was bulging inside the white knickers. I returned to the other room.

Jons face lit up with excitement

"Wow you look so sexy " he said " I promise you'll enjoy this"

Jon kissed me, took my hand and led me to the bedroom.

We got on the bed and began kissing, Jon was fondling my hard cock through my knickers and telling me how much he wanted me. I changed position and started to suck Jon's cock, feeling it harden in my mouth. I was really getting into the cock sucking when he pulled away from me

" Take off your knickers babe."

I stood up and Jon removed them, leaving me standing in just stockings, suspenders and a rock hard cock leaking pre-cum for him to view.

He went to a drawer and showed me a tube of KY jelly

"This will make it easier. Get on all fours on the bed babe."

I felt the cold jelly being rubbed around my hole and then, the moment when he started to insert a finger into me. It didn't go very far as i was so tense.

"Relax babe just relax," as he gently continued to probe my hole, I could feel his finger pressing and I guess i relaxed enough for him to fully insert his finger.

It felt weird but i was also enjoying it. Jon started finger fucking me and after a bit it began to hurt a little bit again as he put two fingers up me. Once id got used to that feeling, the finger fucking started again with him alternating between fingers and his thumb.

l felt more KY being applied.

"Move forward on the bed a bit."

He climbed onto the bed and I felt him rubbing his hard cock up and down my crack., then his the head of cock pushed up to my hole and I felt the tip slide in.

This was different though, it felt bigger than the fingers and once again a burning sensation returned. Jon continued to push the head in and out slowly, inching himself further up me. My virgin arse felt on fire.

"Your doing fine babe," he said as he continued to slowly fuck me, he was probably about halfway up me but i was still holding back preventing him from going all the way.

I felt his hand start to caress my balls and suddenly a sharp pain as Jon finally pushed his cock fully inside me. I was moaning, partly with the pain and partly in pleasure.