So, my man, Callum, has a well-documented desire to watch me get cock, but a holiday to the Costa's gave him more than he’d been expecting. Me too, incidentally, but let me paint the picture for you... Â
We had a week in the sun alone together, after a very long and challenging year. We’d been relaxing for a few days, doing the usual touristy things, and had taken a hint of colour from the sun. One night, we opted for a bar in the party area as I fancied a couple of cocktails. We’d had a light dinner before and were feeling chilled, sat at a table on the edge of the bar’s terrace, watching the world go by. Well, watching the clientele get younger and more drunk to be totally accurate. Â
Deciding to have one more “for the road”, my man went off to the bar to order. He must’ve visited the gents, or there was a delay at the bar or something, as he was gone a good five minutes. And I’d attracted the attention of a small group of lads. There were maybe five guys, probably between nineteen and twenty-two years old.
From what I could hear, they were merry but not totally drunk yet and seemed to be decided who was going to be the one to try their luck at chatting me up. Although I was old enough to be their mother, I didn’t look it, so I ignored them and continued people watching. Â
Next thing I know, there’s a young lad slipping into the chair beside me. Raising one eyebrow, I asked if he was ok. He looked like he wanted to vomit! I’d estimate he was the youngest of the group, around five-feet-eight-inches, dark closely cropped hair but piercing blue eyes. Athletic build, which lent to the image of youth. Â
“My name is Josh. I’m here to save you from boredom and weird-looking drunk guys who think they can sweep you off your feet,” he blurted out. Â
“Oh really, that’s very sweet of you Josh. How did you win this position tonight?” I asked. Â
“What do you mean?” he stammered. Â
“I heard you and your friends earlier. It’s ok, you can be honest with me.” Â
“They dared me,” he whispered shamefaced. “We’ve been here for almost a week and they’ve all hooked up, so they’ve been teasing me. I saw you when you arrived and thought you were gorgeous.” Â
“What is the basis of the dare Josh?” Callum said from behind me. He told me later, that he’d seen Josh be physically pushed to come over, so had given the lad a few minutes. Â
“They dared me to chat you up and leave with you,” Josh said to me, as though I had asked the question. The poor lad had turned white. Â
“I’ve been on a lads' holiday, it’s ok. Let me get you a drink and we’ll see if we can help you out,” my man offered. Â
Chatting over a drink, it transpired that Josh had a girlfriend in the past, but his friends were convinced he was a virgin still. They had been teasing him the whole holiday and nothing he said would get them to leave him alone. So, he’d agreed to the dare. And we agreed to help him. Â
I left the men to chat whilst I made use of the facilities and returned to find a now-familiar look on my man’s face. Josh had gone to relieve himself, so Callum quickly filled me in. Josh had one previous girlfriend, as he’d said, and they had enjoyed a simple sex life while together as were both virgins before. Josh had admitted, with a little prompting no doubt, that he found me very alluring, so Callum had the idea of a little education.
Knowing that I like the dark hair and blue eye combo and that I rarely refuse my man’s requests, he’d made the indecent suggestion to our young friend. Considering the length of time Josh was taking in the bathroom, we wondered if he’d run, but after a while, Josh returned to our table, looking as scared as he did the first time he sat beside me. Â
“Josh, you don’t have to do anything you don’t want to do,” I tried to comfort him. “You are an attractive lad, and I would be happy to help broaden your horizons, but only if that’s what you want.” Â
“I think you’re a gorgeous woman. I’m not sure whether this is a wind-up, but if it’s not and I wimped out, I’d always wonder and kick myself.” Josh gulped some air. Â
“Callum occasionally likes to watch me fuck another guy, and we have taught one lad a few lessons before. There are a few rules we stick to, but the main one is everyone is comfortable or nothing happens. Callum stays, there’s no mouth to mouth kissing, no means no, and whatever happens stays between us, ” I explained. “We’re going to head off after this drink. Do you want to walk with us and think about it en route?” Â
With a nod, we all finished our drinks and set off. Â
Arriving at our hotel, Josh dithered for a moment, then seemed to square his shoulders and straightened his spine. With another nod, he opened the door for me. Â
In our room, Callum got some water for us as I waved Josh into a chair. Dropping my bag on the dressing table, I ditched my heels. Gesturing to Josh’s lap, I asked, “May I?” Â
He looked unsure, so I just settled myself in his lap. “You can touch me if you like. I only bite if you ask nicely.” My comment fell flat, he just looked more nervous. I kissed his jaw and nibbled his neck. I put one of his hands on my knee, the other on my bum. Still, he was scared to move. Â