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Breaking the rules to lose virginity

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By *busyboy OP   Man
1 week ago

Battle

I am sure, I am not alone in having fantasies but for many reasons (confidence/opportunity/right partner) not acting on them.

My biggest fantasy since my late teens was to be used by older men and be breed, however my number 1 rule when meeting anyone is no bareback.

I have only met a small number of guys over the years but one thing they had in common, they were all over 60. Having a baby face and being only 5'5" (on a good day) I loved being a younger toy for them to play with.

Despite trying a number of times, I was very tight and I just couldn't manage to be penetrated, which was incredibly frustrating when you are gagging for it.

Whilst on a trip last year, I met George. He was late 60's, tall, slim, handsome and a rather large cock (the biggest I have played with to date). I arrived at George's home soaking wet, with a quick hello at the door George ushered me into the kitchen where I could pull off all my bike gear. As I removed each damp layer we kept our eyes on one another, with the electricity between us building until I was stood there in just my tight boxers.

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By *aygordon999Man
1 week ago

Shetland

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By *uriousjimMan
1 week ago

middleton

🍆💦

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By *illmecreviceMan
1 week ago

Reading

Nice start

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By *ashtoolMan
1 week ago

belfast

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By *ich65Man
1 week ago

Chorley

🔥🔥😈

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By *ark jerseyMan
1 week ago

jersey

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By *teveapriestMan
1 week ago

Kearsley Bolton

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By *over40Man
1 week ago

aberdeen

Boxers under cyclinggear?

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By *ravelguyMan
1 week ago

Ipswich

More please

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By *busyboy OP   Man
1 week ago

Battle

[Removed by poster at 30/10/25 13:18:15]

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By *busyboy OP   Man
1 week ago

Battle


"Boxers under cyclinggear?"

Motorbike gear

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By *busyboy OP   Man
1 week ago

Battle

George move towards me and we embraced, kissing passionately. He took my hand a lead me to a bedroom where we spent the next hour, kissing, cuddling, sucking and exploring each other. I was filled with lust and offer him my arse. I rolled a comdom down his long shaft and bent over, giving him full access as plenty of lube was applied. We tried multiple positions, but the pain was excruciating and seeing this on my face we stopped and finished each other in a 69.

After I cum, I normally lose interest and looking for the door but we laid in bed and chatted and cuddled for quite some time after.

As I rode away, with George waving me off, I knew I had to see him again and luckily the feeling was mutual.

Over the next few months we exchanged messages and became closer, where I shared with him some of my fantasies.

George was going to be staying in a hotel close by in the coming weeks and asked if I wanted to join him for an afternoon, to which I eagerly agreed too.

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By *eadar123Man
1 week ago

dublin

More please

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By *ich65Man
1 week ago

Chorley

🔥🔥😈

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By *llie74Man
1 week ago

Pyle

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By *busyboy OP   Man
1 week ago

Battle

Two days before we were due to meet, he sent me a picture message which was a health check showing a clean bill of health and said that not using a comdom may help his cock slip into my more freely. I felt flush, a guy I really like who proved he was clean wanted me as much as I wanted him. I skirted around the subject as this was my number 1 rule.

We arrange for George to pick me up at the train station. As I stepped off the train, he was waiting at the gate for me, we shared a smile and we walked to his car parked outside. I was very nervous incase anyone I knew saw me. We chatted like old friends and we travelled in 10 minutes to the hotel.

We went straight up to the room and before the door had shut we were kissing and pulling off eachothers clothes. As I hooked my thumbs into his underwear, I dropped to my knees pulling down his pants, started to worship his cock whilst looking up at him. He looked down at me and said, you can call me daddy, this turned me on even more that I removed his cock from my mouth and slapped it on my face with a massive grin. He pulled me to my feet and we kissed, our tongues dancing around and our cocks rubbing together.

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By *icky13Man
1 week ago

Didcot

More please

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By *unwithuMan
1 week ago

Manchester

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By *eightonpa1Man
1 week ago

Scarborough

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By *ark jerseyMan
1 week ago

jersey

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By *erry55Man
1 week ago

Portlaoise

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By *busyboy OP   Man
1 week ago

Battle

We moved to the bathroom, and hopped into the shower, with George behind me I could feel his cock resting against my bum as put shampoo in my hair and rubbed shower gel over my body. I was so relaxed and the groans of pleasure from him as I pulled my cheeks apart to give him full access to my tight virgin hole.

Once all the suds had disappeared, George stepped pass me onto a bath mat and said take your time, I will be waiting for you, taking a towel with him to dry off. Although I had douched before leaving home, I gave my self I quick once over and grabbed a towel to dry off. Still a little damp, I walked into the bedroom to find George laying on the bed waiting for me, with a pillow in the middle.

He held out his hand to usher me over. We kissed intensely again, then sat up onto his knees tapping the pillow. I slid my bum onto the pillow and laid back, raising my bum slightly above my head. I opened my legs allowing George to move between them and he started rubbing his cock over my balls and arse. On the bed was also lube and some comdoms. George looked at me and asked which should grab.

My mind went crazy, going backwards and forwards, bareback is to risky, I might be able to lose my viriginity, this is rule number one, haven't felt like this before. Words just seemed to tumble out of my mouth, "I want you to fuck me." With that George picked up the lube.

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By *illitMan
1 week ago

Knaresborough

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By *ndstorm45Man
1 week ago

Wakefield

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By *ich65Man
1 week ago

Chorley

🔥🔥🔥🔥😈🥒

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By *busyboy OP   Man
1 week ago

Battle

As George presented his bare cock against my hole, I felt my cock thob knowing I was breaking my rule. George applied pressure and amazingly I took the head of his cock without to much discomfort, I could see the smile of his face growing just as we hit a wall. I felt a shooting pain, and we had to stop, I tried to relax, I wiggled my hips then felt a pop. George was in me, and started to fuck me slowly. The pain had disappeared and replaced by pure pleasure. George lifted my legs onto his shoulders and began to increase the pace, I felt like I was going to cum without my cock being touched.

With my eyes closed loving every second, George asked where he should he cum, I looked at him and said, "breed me daddy" and a few deep thrusts later I could feel his cock twitching as he came deep inside me before falling on top of me, kissing me and holding me tightly. We stayed like that for a while until his softening cock fell out of my stretched hole and I felt his cum start to dribble out. George lifted himself and started to suck me and within seconds I was cuming in his mouth. With his mouth full he lent forward and we shared a sloppy kiss.

We laid together, catching our breathe both smiling with pleasure. An hour had passed in what seemed liked minutes. We took turns in the bathroom cleaning up before we re-dressed. Just before we left the room we kissed again with George whispering my ear, "your my boy now". I felt my cock grow and I wanted him again but time was against us. We held hands on the drive back to the station, and we parted ways with a smile and a wink.

As I sat on the train home I could feel cum still leaking from me, I felt like a slut, I loved it.

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By *ich65Man
7 days ago

Chorley

🔥🔥🔥🔥😈

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By *oy2017Man
7 days ago

Frome

Such a nice way to lose one's virginity. Hope they had some good times after.

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By *ornysuckerMan
7 days ago

Portsmouth

Lovely story I do hope there’s more to tell

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