Testing relationship boundaries

I wanted to share a short story of mine that happened a little while back.

I’m no writer so I apologies now for the grammar, spelling and the rather amateur story telling skills.

It’s a tame story compared to some others on here, but this is a memory I still think about today.

While the facts and the outcome of this story are completely true, the who said he said she said bits are slightly spiced up.

As I said, it happened a while back. I was a young 23 who had recently started a relationship with a stunning 21 year old girl (let’s call her Lisa). Lisa had looks any man would lust for.

Standing at 5.8ft, slim, firm and very fit. Her skin was blemish free from top to bottom. A golden tan with lots of curly brown hair. Her body was in perfect portion, a bubble ass, firm breasts and long slim legs.

From the moment we first met the chemistry was hot.
She dressed to trill. Short skirts and buttoned blouses was her thing and every night out with Lisa was a trill.

We quickly found out we shared some of the same vices.... we liked to be daring and a little kinky at times.

The more we drank the bolder we both were and this night was going to be no different.

Lisa wasn’t into wearing a bra on nights out if she didn’t really have too. Her blouses would always be unbuttoned to teasing levels and her short skirts always got her the desired attention.

After a few months of seeing each other we decided to book a weekend away to the coast. The hotel was a small independent boutique style hotel. It’s the sort of hotel where the receptionist was also the barman.
When we checked in I noticed the receptionist checking Lisa out and she played along with some playful flirting back.
He was slightly older than us but I could tell he was enjoying the flirting game.

We got to our room, had a quick shower and a change of clothes. We headed out for a nice meal and a few bottles of wine.

The drinks soon had the desired effect on Lisa and our conversation quickly turned a lot more flirtatious. I was soon daring Lisa to undo a few more buttons on her blouse and flash a little more thigh. The waiter got a good view but not quite the show I wanted.

Once we finished our meal we headed back to the hotel for a quick night cap then back up to our room.

When we got back to the hotel our receptionist was now the barman. I could see the look in his face.... His eyes were clearly undressing Lisa. Lisa was equally enjoying the attention. She had undone a further button on her blouse and was clearly wanting the barman to see a little more.

A few more on the house drinks later and a few quick glimpses, but still way to shy to be showing anything more, we decided to head back to our room.

We were both feeling the affects of the drinks by now and both feeling incredibly horny. We didn’t want the night to end.

We started talking about the flirting and how she tried to flash her tits to the barman.
I asked her how far she would dare take it? Lisa’s response was to say ‘dare me’!
WoW was all I could think of saying.
How about I call down and ask him to bring more drinks to our room and catch you topless?
Is that it? Lisa said.
Ok, I said, how about you take all your clothes off and he sees you naked?
Hmmm... Not sure about that, but I will go naked under a sheet covering my pussy and I will pretend to be asleep passed out.
Ok... I said but I will play with your tits in front of him.
You know playing with my tits drives me crazy, was Lisa’s response. That’s the dare.... and if you like it; I’ll let him play with your tits while you’re pretending to be asleep.

A few drunken giggles later....Lisa finally accepted the dare only because she thought I would back out.

I tried calling down to the bar but no one was answering. We almost gave up but I said I would go down and order a few more drinks.
I quickly got dressed and headed to the bar.
I ordered some drinks and asked for a few more to be brought up.
The barman said no problem but he was now off duty and his colleague will now be bring the drinks up.

I headed back to our room to tell Lisa.
However, a sudden thought passed through my mind.

Don’t tell her it won’t be the barman coming with our drinks.

I got back to our room and told Lisa it would be about 5 minutes and the drinks will be here.

We were both feeling horny again and I’m sure Lisa was expecting me to stop her going through with the dare.

Lisa was already naked and her pussy was already looking amazing and wet. Lisa didn’t like hair and preferred the smooth look.
I covered her with a sheet, making sure one side of her body was partially visible to see.
I told her to keep her eyes closed and not to open them.
I told her she needed to convince him that she was asleep passed out.

Ok... no problem! Was her reply. Again, thinking I would pull out of the dare.

My heart was pounding so hard.... when suddenly there was a knock on the door....

A quick look at Lisa and she smiled and said do it....

I opened the door expecting to see a young man but to my shock. There was this rather ugly, old balding over weight man. He had the look of someone who had never seen a naked woman (what ever look that is), but I’m sure you get what I’m saying.

Do I stop this.... I thought, but instead I just said come in.

As he walked in he placed the drinks on the side table and turned to be greeted by Lisa very much pretending to be passed out on the bed.
The look on his face was priceless....

I moved to the bed and while thanking the old guy, I placed my hands under the sheets and started playing with her tits. I knew this would drive her wild. I slowly started pulling down the sheet. Lisa continued to play her part but I could see her nipples harden and with that her tits came into view. The old guy stood frozen to the spot.

I could tell Lisa was enjoying this and so I continued with one hand playing with her tits while slowly lowering the sheet with the other hand, stopping just above her pussy.

This is where I thought I would give the old boy the biggest frill of his life. I motioned him to come over to the side of the bed and nodded to him to touch her tits. His eyes widened and the look on his face was that of a naughty school boy. First one hand, then the second hand.

Lisa still had no idea it wasn’t her barman she flirted with earlier.
However, Lisa was visibly enjoying the touch of two men playing with her tits.

I wanted more....... so i slowly lowered the sheet to expose her pussy.

The old boys face was again priceless and was now clearly getting very excited and as I lowered my hand to play with Lisa’s pussy. She allowed her legs to spread for a better view. Still Lisa continued to keep her eyes closed and I thought why not....
I signalled for him to play with her pussy.

I watched for a good 10 mins while Lisa got a good fingering by this old boy.

I was just thinking about how far to push this when Lisa moved her hips and opened her eyes. He got spooked and pulled out, looked at me and then back at Lisa, before making a quick exit.

Lisa looked at me when she heard the door close.

So.... she said. I told you playing with my tits drives me crazy.

WoW...... you saw him! You knew!

We both had big smiles on our faces....

This opened a whole new world for me and Lisa. It lead to more dares and crazier nights out.

I have more daring adventures with Lisa to share..... all are real experiences but with a little extra spice. Our oversea holiday was the wildest. It crossed so many more relationship boundaries...... on so many occasions.

Hope you enjoyed this fond memory of mine....

I’ll share more memories of my time with Lisa if you like this one......

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