An Older Man
A married curious guy meets an older guy to lose his virginity
I have always tried to be a faithful loving husband and father. However, I have also always been drawn to gay sex. I don’t know why and probably never will, but the nights I have stayed up late and masturbated to gay videos or stories would be countless. Even as a young teen I remember the secret urges.
In the end at 43 years old, I decided to fulfil my fantasy and finally took the plunge by joining a swinging website. I naively thought that it would be easier if a woman was present.
Being quite nervous of male contact, I thought perhaps a MFM might be the best way to start, then an MMF and finally I could reach my goal of MM, MMM or even MMMMMM!
This last one seemed pretty unlikely though.
For what seemed like ages I couldn’t get or find the right couple and after only a few days realised that most swinging couples don’t want single, slightly overweight, hairy, 43 year old guys joining their nights of passion. Even though some of them look like Mr and Mrs Greasy Trailer Park Hippo, they are mainly after trim, young couples that look like they belong in Dynasty. I gave up on that idea.
I wondered if perhaps I should skip the MFM and MMF stage all together and find a gay website to search. After around three seconds of searching I found the most popular website. Where had it been all my life? Gay guys openly advertising for meets. Some of them lived a few doors away. (I dismissed those straight away for fear of being caught).
I joined the website on a month’s subscription and began searching for my ideal man. For some reason I thought that an older guy would be better. He should live more than twenty miles away, and be ordinary looking. (I didn’t want to feel outdone when it came to the body and health department).
Just by reviewing their sites I started receiving messages. The first message was from a guy who lived around 22 miles away, was 50 years old with a slight belly, quite hairy and really gentle looking. (Something you would have wanted your Granddad to look like when you were a kid).
I decided that he was the one and started messaging back.
He was single and claimed to be versatile. (I wasn’t sure about me and the top/bottom thing and thought it would probably work itself out during the course of the session). I decided I would tell him the versatile thing worked for me too.
His name was George and had been married with kids before he came out, he seemed to understand what I was going through and said he was cool with that.
After a couple of evenings chatting I decided that we should meet and have some fun. George kept repeating to me that he wouldn’t do anything I didn’t want him to. Shame really as I wanted him to show me everything all at once and get it over with. You must know that by now I felt obliged to every gay guy in the world that I should try everything at least once.
Just some info for you, my wife, Sarah, is great in bed and in the past has fingered and rimmed me several times. This was an advantage as I knew all about cleanliness and how to douche before a session. I would be mortified if I accidentally let one go during a session.
So on the evening of the meeting with George, I told Sarah that I was going out with some friends from work to celebrate a birthday. Sarah asked about three million questions about the evening, but I had scripted this plan so well it was infallible. I quoted every pub we were going to, every drink I had planned and named all the guys going. I carefully chose work colleagues she didn’t know.
I slipped into the bath and cleaned myself really well, both inside and out in preparation.
After dressing, I kissed the wife and kids and headed out. Finally the night had come. I was going to lose my gay cherry.
I jumped into the car and headed toward Georges house.
The journey seemed so short that I had no time to think of a plan of action and several times thought about turning around. If it wasn’t for the fact that I would have to find a secluded place to park for a few hours to let the time pass I probably would have gone home.
I parked the car just outside Georges address. He lived in a really well maintained bungalow with flower baskets and picket fences, the works. It felt welcoming immediately.
I walked up the path to the door and gently tapped it. Wild barking followed. George didn’t tell me he had dogs. Why would he? Not the sort of thing you would discuss whilst chatting about whether or not swallowing cum seemed ok or not.
George opened the door. He seemed a lot older than the years he had confessed to, and certainly a lot more portly than the picture he had sent me.
He smiled at me and without saying a word beckoned me in whilst trying to hold back the tiny dogs than were still barking and wrestling with him to get at me.
As I walked past him, dread filled me. What on Earth was I doing here? All I could see in my mind was my wife’s face. Fifteen years of marriage to a wonderful woman were torturing me.
“Would you like a drink?” George asked.
“Yes please, Tea”, I responded. What an idiot I was. George obviously meant an alcoholic drink, but the moment took me by surprise and tea was the first thing I could think about.
As George offered me a seat I took the opportunity to look at him properly. He was wearing grey pleated trousers, a worn green cardigan and a pair of slippers. Hardly the seduction outfit I was expecting. His hair was grey and thinning and although his face seemed really well maintained, the spectacles he wore looked like something a vicar would wear on the end of his nose during a sermon.
He must have been gone for a good five to ten minutes. I looked around the room. Pictures of people in ornate frames appeared everywhere and hardly an inch of the walls lay uncovered with a lifetime’s collection of bric ‘n’ brac.
George returned to the room. He was carrying a tray of cups with sugar and milk on the side. Thankfully he was dogless.
He placed the tray on the coffee table and sat next me. So close he was practically on sitting on my lap. My left leg was hard against his right leg, and out of instinct I moved it away.
“How are you feeling?” He asked “Nervous?”
“You could say that, George” I said.
“Actually it’s Henry,” He replied
Now I was confused. “Sorry… Henry?” I questioned.
“Yes, I never call myself by my real name on line, it’s just a bit of a risk with the location there” he added
Not helping my nerves I thought. Shit, what if someone realises that Richard from the midlands is me… I took a deep breath and just thought how unlikely that was. Stop panicking I told myself.
“Do you want to watch a DVD to get in the mood” George asked
The way things were going it was more likely that I would pop out of the window and run home before I let this guy pop anything of mine. “Good idea, George” I replied. “Henry, I mean” I added.
George or Henry or whoever got up and headed toward the TV set. The TV set looked like something you would see on the commercials during Starsky and hutch from the 80s.
He inserted the DVD and returned to the sofa. Again he was practically crushing my left leg as he took his seat next to me again. The DVD started running and two guys who were definitely extras from Starsky and Hutch appeared on the screen.
On the DVD, the first guy was undressing the second and as he pulled the tight T shirt from the thin moustachioed hippy he started kissing the hippie’s nipples. This is quite hot I thought.
I felt George shift a little and brush his right arm gently against my left. As I turned to see what George was doing the movements from him seemed a lot heavier. Oh my god He was undoing his fly. I sat there now seriously thinking about running away, but it was too late. George or Henry had by now taken out his cock and was gently rubbing it.
What an ice breaker. A familiar stirring started in my groin.
I looked in fascination at George’s manhood. For an older guy, there was definitely an attraction to him. “Why don’t you join me?” he asked. He didn’t have to ask twice.
I undid the belt and buttons of my jeans and pushed them down to just above my knees. My briefs followed. My cock was kind of semi hard at this point. I put it down to nerves and started rubbing it in unison with George. If there was a gold medal for synchronised wanking, George and I would probably have won. I could feel my cock now getting harder. ‘Good boy,’ I thought.
Turning to face George again I noticed he was well away now. Lost in his own fantasy world. His hand was moving almost faster than I could see. ‘So much for a slow start then,’ I thought. He was sitting back on the sofa, eyes closed concentrating on wanking himself off.
I was puzzled. I hadn’t driven 20 odd miles to sit in front of a 70s Television playing a crap 80s porn film to crack one off with a guy I didn’t really know. I could have done that at home. Obviously the guy bit couldn’t have been done at home, but you get meaning.
I continued rubbing myself with my right hand and took the initiative. I placed my left hand on George’s now exposed thigh. George jolted as if I had an electric current running through me and looked at me questioningly. “Would you rather be on your own?” I asked in all seriousness.
He smiled “Sorry was I neglecting you?”
With that he stood up and pushed the coffee table to one side. The now probably just right for drinking tea, split over the rim of the cups as the table stuttered over the deep pile carpet. I amazingly wondered for a second if I should take a quick slurp. With his trousers around his ankles, George performed a kind of penguin walk back over to me. He then knelt in front of me, pulled my Jeans right down to my ankles and quickly followed them with my briefs.
I knew what was coming next and closed my eyes. I felt a hot mouth engulfing me. I sighed. Not a normal sigh, more like a really uncool loud seal yelp. George or Henry (At this moment I would have called him the messiah) started moving his head up and down, gently but firmly taking my foreskin with him on each movement. I don’t think any man can say he’s had a great blow job until he’s received one from an experienced guy. I was now rock hard. I opened my eyes and looked down as George looked back up at me. That was a bit of a spoiler really. A huge tanned bear wasn’t sucking my knob after all; it was an old bloke with a wrinkled forehead. Fuck it, still felt like heaven though. Suddenly George stopped. “Shall we go into the bedroom?” He asked, his hands still perched on each of my knees.
‘This is it’ I thought. I am finally going to feel a cock inside me. By now my nerves had been completely taken over by passion. I would have leapt through the walls to the bedroom if I could.
I stood up and followed George out of the room into the hallway. Note to self: If ever I am lucky enough to be in this position again, please either pull the jeans back up or completely remove them. Two guys walking quickly in single file taking pigeon steps down a fifteen foot hallway isn’t one of the sexiest sights in the world…
We reach the bedroom. A large double bed on the left of the white walled room and fitted wardrobes to the right. Like the rest of the house the bedroom was immaculate although a little frilly.
The consistent barking that emulated from behind the closed kitchen door remained.
I continued to follow George as he stopped and turned around to face me by the side of the bed.
“You don’t need this.” He said gently tugging my sweater over my head in one movement. He then started unbuttoning my shirt and let it drop to the floor. There I stood semi naked with my jeans and briefs still around my ankles. I stepped out of my jeans and briefs and calmly sat on the bed to remove my socks. George remained standing in front of me. An older man with his trousers and pants around his ankles, an old green cardigan hanging past his mid drift and a fully erect cock pointing at the heavens.
Not sure what made me do it, I guess it was the heat of the moment, but my right hand reached up and began massaging his cock. Like me George was uncut. His cock was smaller in girth to mine but it felt slightly longer. I think years of wanking have made my right hand the most accurate penis comparison tool in the world. It can measure the difference to the millimetre. It was difficult trying to keep the momentum going as George was now undressing and perfecting the stroke seemed practically impossible. I decided to let go and sit back. George finished undressing but for some bizarre reason left his grey socks on.
“Where were we?” He asked and again fell to his knees. His hot mouth took me again. This time he went the whole length of my cock right down to the base. No woman had ever managed this before. More to do with the women I had been with than the size of my cock.
George increased the pace. It was incredible. “Stop” I shouted. I could feel myself about to cum and although he gave great head, I would have felt disappointed to have cum so early. George carried on. My knees began to shake uncontrollably and my cock erupted in George’s mouth.
He swallowed every drop.
“Fuck” I sighed, laying back on the bed. “That was incredible.” George stood up and smiled at me.
He moved to my side and lay next to me on the bed. “I aim to please.” He responded.
I lay there beside George in silence, looking at the ceiling, contented. Thoughts of my family had selfishly been pushed to the back of my mind.
I did feel obliged to return the favour, but was a little concerned that my oral skills may be a little lacking. Turning on my side facing George I reached down and began massaging him again.
I moved down to his mid drift so my head lay on his waist and took the tip of his cock into my mouth. His taste hit me at once. It was not unpleasant though. After a few seconds his taste seemed to almost disappear. Still rubbing the base of his cock I took in little more of his cock and could hear him moan above me. I wasn’t bad at this. The moaning seemed to get a little louder and I was more than prepared to let him cum in my mouth. It wasn’t so much of a blow job, more of a wank into my mouth. The passion that I expected to dissolve after shooting my load still remained.
George stirred and pulled my shoulder back forcing me away from him. Was I doing something wrong? “Get on all fours,” he whispered.
It was as if I were under a hypnotic spell. If George told me to run around impersonating a chicken I probably would have. I got on all fours. George climbed on the bed behind me. He started gently kissing my bottom. His mouth moved from my cheeks to my crack. I could feel him parting my cheeks as he began lick my hole. His tongue flickered over my hole for a few seconds sending me into oblivion. Then it happened. He pushed his tongue right inside me. Oh my God, that was intense. Further in the tongue went. Precum was now dripping from my cock again onto his duvet. George had hold of the top of my legs and was pulling me back toward him pushing his tongue in deeper.
As quickly as he slid his tongue in, he took it out. “Hang on” he sighed.
Still on all fours I looked behind me. The bed moved and George on his knees behind me reached to a bed side cabinet and took out a small clear bottle and something else.
I felt dripping liquid on my crack followed by a finger entering me. I closed my eyes. A second finger was pushed in with the first and gently massaging started inside me. More liquid was dripped on me. The feeling of two fingers inside me was a feeling I can’t explain. But it felt as though my hole was being stretched to its maximum.
George slowly removed his fingers. My heart was racing. “Are you OK?” George asked.
“Are you kidding?” I replied. “Stop now, and I‘ll kill you!”
George laughed as he ripped open a packet.
It seemed like I was waiting for a lifetime. I felt Georges cock head rubbing against my hole. “Relax..” George whispered as he gently pushed his cock inside me. Unknowingly there I was on all fours, my fists clenched in his duvet. My teeth gritted. As if I was waiting to be impaled on a stake. However, there was no pain.
Gently George pushed a little harder. I felt a strange numbness inside. It was a really nice numbness. To say there was no pain at all would be a lie. But it was a sexy kind of pain. The incredible intense feeling of George pulling out almost fully and then slowly sliding himself back in to his hilt was over whelming. I was now dripping more precum from my cock like I never had before.
My grip on the duvet was loosened as I could hear myself kind of grunting with every one of his movements. He pulled out completely. I felt like punching him. He asked me to turn over and lay down on my back. He placed a pillow under me.
We were almost in the missionary position, me with a pillow under my lower part, George now on his knees between my legs. He pushed into me again. This time I did feel intense pain and pulled away. “Sorry” George whispered. “I forgot you’re not used to this”
I wasn’t going to let one second of pain spoil anything and took my position again. He re-entered me again, this time with controlled force. Slowly he started his rhythm, building to a much faster and harder routine. The pain had now completely subsided. After only a few glorious minutes he cried “Richard, I’m going to cum!” His face looked contorted as he pushed his cock right down to its hilt and held it there. I could feel his cock pulsating inside me. The feeling lasted only a few seconds and he pulled out and collapsed next to me.
“Wow” he breathed. His left arm lay across my chest. I looked down at my cock only to realise that at some time during the episode I had cum again. That was unheard of for me. I had actually cum without any direct touching of myself, even stranger especially after having erupted earlier that evening.
“Fucking wow” I responded. We lay there for a good ten minutes. I still had the pillow under me and George with his used condom still hanging from him.
Fancy that cup of tea now? George asked.
. . .