It all started a year ago when my step-sister and I decided to go on holiday together. Actually, we didn’t decide. I still reckon I was tricked into it, not that I’m complaining.
Best start at the beginning, though our set-up is pretty conventional. My Mum and step-Dad got together several years ago after respective divorces. Each brought a child, a boy (me) and a girl, into the marriage. At the time we were both approaching our teens. After a little initial awkwardness we both got on pretty good and as far as we were concerned we were like a real brother and sister. I got married about 10 years ago to a long-standing school friend or childhood sweetheart, I guess you could say. We were both 25 at the time and the relationship produced 2 kids, a boy and a girl. My wife was (and is) a good woman and pretty adventurous in bed, but, during the marriage we just got into a rut, which led to us arguing a lot. It was over the usual reasons, not enough money and various other family things. So in the end we just split up, went our own ways and got divorced, with both our kids living with their mum. Occasionally she calls in when her new guy, a long distance trucker is away just to get an itch scratched that he can’t seem to reach.
Anyway, let me introduce myself. My name is Sean, I’m 35, just under 6 foot and my middle-aged spread is beginning to show, probably because I am no longer eating that healthily since the wife left. I go out a couple or three times a week with my mates down to the pub or club and just have a good time in general.
Now on to my step-sister; well, she is also married and, I believed, very happily. Her husband is a good bloke who comes out with me at least a couple of times a month and we get on well.
Her name is Penny. She’s 32 and 5’ 2”, short blonde hair and 36C boobs, (I know this because her husband Phil let it fall when he was drunk one day and a little out of control of his mouth). She likes a laugh but is quite conservative with her hubby around; we are close, as in friendly, these days, but not so close as to be seeing each other daily.
This story begins when I was at home one morning looking at some holiday brochures. There was a knock at my door and when I answered it there was my step-sister, Penny.
“Hi! How are you?” she said brightly.
“Fine. Come in,” I replied with a grin at seeing her.
So Penny came in and I ushered her into the living room. She started thumbing through the holiday brochures while I went to the kitchen to make us both a drink.
“Thinking of going on holiday then?” she asked when I took her a cup of coffee,
“Sure am, Sis.”
“So, who are you going with?” she asked.
“Probably on my own,” I replied.
“Oh, that’s a bit sad; you really should find someone to go with you. It’ll be more fun.”
“Like who?” I asked. “All my mates are married and their wives won’t like the idea at all.”
“Well, I could go with you...”
“You must be joking, Sis. Why would I want my step-sister to go on holiday with me?” I laughed, thinking it had to be a joke.
“I was only saying. Keep your shirt on, Sean,” she replied, clearly a bit put out nevertheless.
“Sorry, Pen,” I answered earnestly as she really did look annoyed.
After an hour in which she went over what her daughter, Kirsty, wanted for her birthday Penny left to pick up her youngest from school, which left me at home alone again and some peace. We do get on, Penny and I, but I also like my peace. But I did feel ashamed at how I’d put my own step-sister down about her going away with me. But really, why would I want to go on holiday with my own step-sister anyway? The main point of going from my point of view was to get laid a lot with a variety of different women; sharing a room with my step-sister would limit my options immensely. Christ, the last time we went away was with our parents when we were both kids.
So a couple of weeks went by and I spent the time trying to see if any of my mates were available to go on holiday with me. Trouble is, all my mates are married, so their wives are not prepared to let them go with one of their single mates (and for very good reasons if I was being honest).
I was then invited to my step-sisters BBQ one Saturday afternoon. The occasion was Kirsty’s birthday. I got a taxi to her house, knocked at her door and was let in by my 14-year-old niece.
“Hi, Uncle Sean,” Kirsty greeted me as she was functioning as the welcoming committee.
“Hello, cheeky, and happy birthday,” came my reply as I handed over the delicate bracelet she’d been hinting at. ‘She’s going to be an absolute stunner when she gets older,’ I thought to myself, appraising her developing figure.
“Sean, glad you’re here,” shouted Penny from the back-garden as Kirsty thanked me for the gift then ran off to show her mates. “Go and put your beers in the fridge,” Penny added, which I did and took one of Phil’s (Penny’s husband) cold beers and went to join the rest in the garden.
Soon the beer was flowing and we were all having a good time. Phil was doing all the cooking, Penny was playing the good hostess to the other guests and the kids were mostly behaving in the background. About 10pm most people were starting to go home which just left Penny, Phil and myself, Kirsty having gone with one of her friends for a sleepover.
“So, who’s going on holiday with you then, Sean?” asked Penny.
“No one yet, Sis,” I replied.
“Why not?” asked Phil.
“Well, none of the lads are allowed to go with this single man. I don’t think their wives trust me not to lead them astray,” I said with a laugh. “Want to come, Phil, or will my step-sister not allow you as well?”
“Sorry, Sean, work commitments, but would have loved to go with you,” he replied with a grin. “All those bikini-clad women,” he finished with a leer.
“I told you, Sean, I would go with you,” Penny added. “Phil would not mind me going, would you, Phil?”
“No. Penny can go with you, Sean. I trust the both of you,” Phil nodded. “Though she might cramp your style.”
“No I won’t ... much,” she giggled.
So with all the drinking and having a good time it was agreed that Penny could come away on holiday with me, despite my better judgement.
The months went by; I booked the flights and hotel. The day came for Penny and I to go on holiday together and, after many hours flight and transfer to our hotel, we finally got to our room.
The hotel was quiet and not too crowded with people or kids which was pretty much why I chose it and Penny was pleased with our room, which had your usual bath, shower and two single beds as well as a pretty good view.
“So, are we ready to explore the area?” I asked as I quickly unpacked my case and Penny dealt with hers.
“Sure. Let me change first though, Sean,” she replied and vanished into the bathroom.
We went out to explore the area around our hotel and found some shops where we could get our water and food and just took in the sights.
During all this Penny was wearing a tight and quite short cream top which exposed her midriff and she did not appear to be wearing a bra, as far as I could tell. She was also wearing a pair of high-cut shorts, and I must admit she did have a nice pair of legs. All those years of going to a gym had definitely worked for my step-sister; I could not see an ounce of spare fat on her.
We eventually ended up back in our room to get ready for an evening out on the town. I showered first and got ready, followed by Penny.
“Penny, I’ll wait for you down stairs in the bar,” I called through to her in the shower.
“OK Sean, see you there.”
Downstairs, I eyed up a couple of the female guests, but had to admit, neither were a patch on Penny, not that that would normally stop me, but with Penny with me, it really wasn’t an option, which was the main reason I’d been reluctant to bring her. She was a definite cramp on my style. Eventually, after my second bottle of beer, Penny turned up wearing a simply stunning outfit, tight pink top, which was also off her shoulder and showed off her still perky boobs, along with a very short black skirt, which made her legs look great.
“Penny, you look simply gorgeous,” I complimented her with a slight gulp as I knew I was with the most gorgeous woman in the hotel complex.
“Thanks, Sean. I hope I look OK,” she replied with a slight blush.
Well, the evening went really well, we had a good meal and just chatted about our family and things we used to do when we were younger. I did have to be careful, my eyes were constantly drawn to Penny’s boobs and not her face, but I don’t think she noticed, or minded. Nor was I bothered about not being drunk and on the prowl for an easy lay either. If anything it was fun as we lightly flirted with each other, avoiding anything over the top.
The next morning we decided to spend the day down at the beach just relaxing. I found us a couple of sun beds and, after a swim; I took my top off and lay down. Penny had just paddled, so as not to mess up her hair, she said. She then took her top off to reveal a perfect pair of still perky boobs held in a bikini top and then bent down to take her shorts off to show me her bikini bottoms, making me almost groan in suppressed lust at an absolutely divine rear end. Penny then got on her sunbed and lay on her stomach.
“Sean, will you do me a favour and put some cream on my back? I don’t fancy looking like a lobster,” she requested and then untied her bikini straps. I took a handful of lotion had started to rub it all over my step-sister’s back, glimpsing a side view of her boobs as I did so, whilst concentrating heavily on suppressing my burgeoning erection.
After about half an hour Penny looked over at me and said, “Sean, I feel embarrassed to ask you this, but do you mind if I go topless? I know I’m your step-sister but would it bother you?”
“Penny, if you want to go topless then be my guest. You might be my step-sister but you’re also a beautiful woman with a bloody good figure so why not show it off,” I told her with a slight swallow.
With that she rolled over on to her back, sat up and dropped her bikini top to show the world her boobs. Boy, they did not disappoint as the sudden amount of drool in my mouth was telling me.
And this is how the holiday continued. Penny always going topless, me putting lotion on her back (which she also did for me) and looking really, really good when we went out in the evening. And yes, for all she’s my step-sister, I was seriously tempted at times as it had been a while and she was sort of flaunting it a bit when we were out and putting a cramp on my intentions to get laid as often as possible with as many women as possible.
Our holiday was coming to the end of our first week. Nothing had happened between Penny and myself. I was of the opinion she’d just scream and run a mile if I did try anything, tempted as I was at times and suspecting she knew the effect she was having on me, although she didn’t let on. Indeed, all there was, was me just getting horny with seeing my step-sister topless, having never seen her boobs before. What with all the sun and beer, it was having a definite effect on me. But with Penny I just was not sure if she knew or not and I was becoming increasingly frustrated sexually. I was resorting to shaking hands with myself in the bathroom each night and yes, Penny was the woman my lurid imagination was fantasising over.
On this day though, the time had come for our evening out and Penny looked fantastic as usual. We went to a bar after our meal and when we were settled in a corner with our drinks Penny said to me, “Sean, thanks for letting me come away with you. I’ve really enjoyed myself.”
“Penny, it’s been my pleasure to have you accompany me and I must admit I’ve enjoyed seeing you topless,” I replied, a bit embarrassed with my last comment as it was the beer talking.
“Sean! Have you been looking at my tits?” she asked laughing.
“Well, they’re quite perky aren’t they?” I chuckled.
“36C Sean, and I’m glad you like them. It’s the first time that I’ve ever been topless. Phil would never let me do it. Like he never lets me do lots of things,” she sighed.
“Like what?” I asked.
“Well, he always moans if I go out with my friends and other things.”
“But why would he moan about you going out with your friends?” I asked in puzzled tones.
“Well, I suppose it’s because I dress a bit too tarty for Phil’s likes. I do enjoy showing a bit of cleavage, but I don’t get my tits out for the lads, if you know what I mean?” she replied, looking slightly flushed.
As there seemed nothing I could add to the conversation, I bought us both another drink and we soon decided to make our way back to the hotel. This time a slightly downcast Penny wanted to hold my hand, to which I did not object. I very much enjoyed having my hand held by a damned good-looking women, even if she was my step-sister.
We finally got back to our hotel, stopped to have one more drink in the hotel bar and then slowly made our way to our room, both of us having drunk a little more than usual.
“Sean, another drink?” she asked somewhat nervously when got to our room.
“Sure Sis, why not,” I replied. “So, what is it with you and Phil?” I asked, tackling the subject that was apparently bothering her head whilst holding a nice cold beer in my hand.
“Well, it is all about sex ... I want to try things, but Phil is such a cold fish. He never wants to experiment or try anything different,” she told me.
Hearing this from my own step-sister made me get really horny, some of it from the drink but I was also a bit embarrassed that Penny would ever say things like this. Perhaps it was all the beer we had drunk that evening, though I had a feeling she had been working up to this all night.
“What things are these then, Sis?” I asked carefully.
“Sean, when you were married did you and Yvonne (my ex) enjoy sex?”
“Yes, we did Penny, and we did all sorts of things. That was never one of our problems,” I replied with a slight grin.
“Sean, can I cuddle up to you? If you don’t mind?” she asked and came over to me as I stretched out my arms and put them around my step-sister and gave her a what I hoped she thought was a brotherly cuddle, seeing a single tear run down her face.
Penny looked me in the eyes and said, “Sean, you’re a good man. Why have you not found a good woman for yourself?”
“Tonight I have a very good woman in my hands,” I replied taking a chance as I squeezed her tight and then, almost without thinking, I kissed my step-sister on her cheek.
Penny looked at me slightly in wonder and then turned slightly to kiss me on my lips, causing me to open my mouth and slide my tongue into her mouth, which met with no resistance at all. Both our tongues entwined as one. We finally stopped after a few minutes, both of us slightly flushed but clearly very aroused too as we both knew this was going to go a lot further than propriety would normally allow.
“You kiss good, Sean,” she said, panting slightly.
“Not bad yourself, Sis,” I told her, giving her a tight squeeze.
Penny kissed me again, but this time slid her hand onto my cock and gently squeezed it, taking its measure, as it were.
“You sure about this, Sis?” I said, giving her an opportunity to back out if necessary, though hoping she wouldn’t.