tagMatureLibby & Her Sister

Libby & Her Sister

byRed Hugh©

The advertisement intrigued me. I was not looking for an involvement of the sort that eventuated but I thought what the hell and replied.

I should recap. I'm a middle-aged man living alone after a long and unhappy relationship with a woman who was more interested in money than anything else including my or our happiness. I'm not bitter. I'm simply delighted to be shot of her. Her children and I still get along fine but she is not someone I ever want to see or speak to again. I was cruising the personal columns looking for a woman my own age who was looking for a bit of fun - nothing more. What caught my eye was an advertisement for a 'young girl' looking for a sugar daddy.

I replied for a laugh and went to bed masturbating about the thought of a young woman bouncing on my cock.

The next evening I had a reply. 'Libby' was 19 or so she said and lived in the deep south of the country about 400 miles away. She wasn't really what I wanted in terms of age and distance but she was a nice kid and a relationship based on chat and a few modestly posed photos ensued. I got the sense that all was not well with her and this was confirmed one day when I got a text message from her asking for money. Despite wanting a sugar daddy she had never asked for cash or anything other than my attention.


I got her bank account number and dropped $1000 in that afternoon. There was no reply to my messages that evening and I assumed that that was it. Imagine my surprise when I got a call on my cell phone asking if I could meet Libby at the local airport. It's a long drive from my place up in the hills down to the airport. When I say local I mean two hours drive. I'm pretty isolated and I like it that way. Well I got to the airport and saw Libby who looked awfully young. Alarm bells went off was this girl really as old as she claimed. Moreover she wasn't alone there was another girl with her. Running up and throwing her arms around me she gave me a hug but winced as I responded and squeezed her. Under her dark glasses she was sporting a black eye she would have to explain to me later. She introduced her little sister Angela who was similar in looks to her sister but very slender.

To cut a long story short. The girls lived with their drunken father and upon his discovering that his elder daughter was having photo's taken by her sister and posting them to me he beat them both and threw them out disowning them. Angela was 17 and I had them both on my doorstep so to speak.

They both sported bruises so I thought the first stop would be a doctor. They were both a bit nervous but agreed and so we set off. Libby was okay but Angela had a cracked rib and was in some pain. X-rays, pain killers and a few hundred dollars later we were on our way to my place. I still had no idea what to other than to offer refuge. While e-mail exchanges had been fun the reality left me a little flustered. These girls were younger than my daughters!

I should pause to describe Libby. She was about 5'3" and while not chubby had lovely curves that filled out her worn jeans just beautifully. The visible panty line showed she wore full briefs and the way her medium sized breasts moved I could tell she wore no bra. Her hair was a crop of black curls, her eyes blue and her skin white. Her sister was a gangly carbon copy.

As we approached home I still had no idea what I was going to do. Feed them clothe them and try not to get arrested. I tackled the matter of age with Libby and she flashed her passport which indeed showed she had turned 19 a month or two back. At home we eased Angela out of the car and I showed them the room they would have to share. Libby seemed very quiet so I went to pour a bath for her sister to soak in. When it was ready I called her and she and her sister arrived. Libby said she'd stay and assist Angela and I left to get some early dinner ready.

About an hour later they emerged and I was surprised that Libby hadn't taken the chance to freshen up. Angela was in a robe and towel I'd provided. We had dinner and Angela headed for bed.

It was soon after the first glass of wine that Libby downed that she made a clumsy pass at me. Saying she wanted a bath she asked if I'd be joining her. I was still so surprised at the day's events that I asked her to repat what she'd said. She murmured that she wanted me to join her. I declined as gently as I could and Said that she should think very carefully about asking me to get naked with her because there was no question that it would lead to sex.

She smiled and went off alone to bathe. I was tidying up when I felt her arms circle my waist from behind. She was attired similarly to her sister. Towel on her head and a robe. When I returned the hug she winced again and kissing her on the cheek I suggested she head for bed and I'd see her in the morning. She pouted a little and said okay pressing a small piece of cloth into my hand as she headed off with a giggle. I was left standing at the sink with her panties fresh from a day's wear against her pussy in my hand.

She told me that she wanted to sleep with me but that she was too sore to have me on top of her. I began to wonder just what this girl knew about sex given that as a big man I was used to women being on top of me. There was much too much of the outward appearance of worldliness about her to be true I thought.

I still had her panties in my hand and I guess I just gave into temptation but I took her hand and led her to my bedroom next door to where her sister was sleeping. Making sure the connecting door was locked I shut the door behind us and went to sit on the bed to remove my shoes.

She asked if I didn't like her 'present' I told her I was sure I would but we needed to clear up a lot of stuff. She got up on the bed and sat cross legged, under her robe she had a large t-shirt of mine but obviously no underpants. As she settled I caught a flash of dark curls and a pink cleft beneath. We talked into the night about the day and our situation. Our e-mail exchanges had become very intimate but here we confronted a reality. I was still not convinced by her but unless she bunked with her sister there was nowhere else for her and she was of age and I was horny and ...nothing happened. We slept.

I learnt two things that evening. Libby knew damn all about sex. She'd had one fleeting unsatisfactory encounter and that was it. She was a virgin in all but the technical sense as the boy had come about halfway inside her and she'd had all 'the pain and no gain'.

Her sister was a more interesting problem, she was sure that Angela liked women so bang went any fantasies I had for her 18th birthday party. As such it wasn't a massively complicating factor as my neighbour about a mile away was an attractive lesbian in her early thirties. We were firm friends since she got over her wariness of me. Naturally she'd assumed that I'd like to get into her pants but I'd never pressed the point and one Christmas time when the community got together and she'd got very drunk, I'd found her out the back of the hall relieving herself - except she'd forgotten to drop her jeans. I'd bundled her out of the way and taken her home. On boxing day morning there had been a knock on my door. A somewhat shamefaced and hungover Mary had stood there with a little thankyou gift.

To cut a long story short she was thankful and apologetic. We'd had some hair of the dog to liven up and the conversation had drifted to why neither of us appeared to have any obvious companions. That's when it slipped out. I didn't mind I'd just masturbate about her and another woman in the future.

Anyway a platonic intimacy grew and even a few rumours flew which she was okay about as it deflected those who would otherwise purse their lips. I resolved to talk to Mary about the problem at hand.

Libby woke me playing with my morning hard-on. We really did need to sort out a few things. I let her play but begged off after a while to go and empty my bladder. She followed and watched and then hiked up her t-shirt and relieved herself. Taking off her robe and t-shirt she then headed for the shower. God, she looked inviting with her clothes off.

I made breakfast and her sister emerged to eat with me. Libby wandered out of the bathroom and to breakfast drying her naked form with a big soft towel.

Obviously the sisters were comfortable like this even if my cock began to embarrass me. Angela thank God did not notice. I went off and showered and went over the hill to see Mary. She hooted with laughter at my news and promised to drop by. We made a pretty happy little group as time progressed. Libby and I developed an easy sexual intimacy which was only slightly jarred by her sister's presence. Angela knew what was happening of course but being interested in girls and too young she was not a participant. All it meant was that in my own house I couldn't wander around naked as I was used to when I had it to myself or when bedtime companions were around. I'll tell more about my one on one life with Libby in another story but all this leads up to her sister's birthday.

The girls had very, very different personalities, their sexuality didn't account for all of that. Mary and Angela had become very good friends but like me Mary was strictly hands off despite what we both sensed as a growing bond of affection. The four of us were the only people at Angela's birthday dinner. I hired a helicopter to take us out to an island for a lunch on the beach and we had a fair bit to drink so as we landed back at my place in the early evening we were all a bit tiddly. Libby and I toddled arm in arm inside followed by Mary and Angela. We were all casually dressed with just Angela wearing a skirt.

We had a few more drinks and I suggested Mary bunk for the night as neither of us could drive in our condition. We just kept drinking laughing and generally having a good time without any real aim other than fun. We were soon all very drunk. Libby had been on my knee and between drinks we had been kissing. Suddenly we looked around and no Mary, no Angela.

Libby giggled and said we should go and see what they were up to. We found them outside on a big chair kissing. Mary saw me out of the corner of her eye and Angela sensing something disengaged and looked around. All four of us looked at each other and started giggling. Angela was on Mary's knee and I could see up her skirt to the panties she favoured. She was much more 'girly' than her somewhat tomboyish sister and liked lacey little bits of nonsense to cover her tender areas. On her mound I could see a little panel of lace and then the dark signs of her nether hair.

She made no effort at modesty.

She did ask if Mary could really stay the night and of course I told her "Yes". The real problem from now on was Mary and me. If we got any drunker, as looked likely, things would most likely get naked and silly but fun. Angela solved part of the problem by getting up to go to the toilet and took her sister with her presumably to gossip. I sat down with Mary and we both drew a bit of breath. We looked at each other and a whole pile of unspoken matters passed between us. I could feel the familiar vibration of a lost evening turning to a lost weekend of sexual abandon. I simply said

"Are you okay with what's going to happen?"

And she nodded saying she expected things to get pretty dirty and did I mind. Without voicing my desire to see Mary naked I just told her that if Angela was keen we were very happy with what was obviously going to happen.

Mary kissed me on the cheek and at that moment the girls reappeared. Half jokingly Angela yelled

"Hey you're mine tonight" at Mary.

Mary responded by telling her to get over to her and show her she meant it.

"It's too bloody cold. Come inside to the fire." Was the response.

It really was going to be quite an evening as Libby and I had nowhere else we could go the invitation was obvious. Mary was on her feet somewhat unsteadily and went back inside with Libby and me following. The fire was well stoked and we took up the two sofas as two very friendly couples. What might have happened if we were more sober I'll never really know but Libby and I began to act as if we were alone. We kissed deeply and intimately and while still having our clothes on it was clear as Libby straddled me with her back to the others that she was rubbing herself against me.

I was brought back to reality by a little cry opposite us. We both looked around and Anglea was sitting astride Mary with her skirt hitched up and the string of her panties pushed aside. She was gently riding Mary's fingers. Her head burried in Mary's shoulder and Mary smiling at us both. Nothing was left to the imagination. I could see Angela's parted buttocks and the little pink hole into which two of Mary's damp fingers were slowly pumping. Libby tended her nether regions regularly with a scissors not really needing to use a razor. Angela needed both in my opinion. Libby had the curves and Angela was willowy, her parted legs showed everything and the dark matted curls completely covered her slit and hole making the pink of her inside all the more apparent. Her little buttocks clenched and unclenched as she humped for the first time on another's hands.

Libby got off me and sat around to watch. She reached between my legs and rubbed my very visible lump. Soon that wasn't enough as her sister began to really hump and grunt, Libby reached under her own waste band and began to masturbate. God only knows how I kept from soiling my pants.

Mary did an odd thing. As Angela came on her fingers and sobbed into her shoulder Mary pouted her lips at me and quite clearly blew me a kiss. We were very very good friends maybe even loved each other but we knew that we were not for each other -her preferences being a major stumbling block. I was puzzled.

Through the pleasant haze of booze Libby unzipped me. It seemed there was going to be a reciprocal show and my cock was to be the star. I no longer cared who saw what as long as we were all friends in the morning. Down Libby went swallowing my cock as she had learned to do in the months of our shared intimacies. Angela didn't watch but simply unbuttoning Mary's blouse began to suckle on her unbound breasts. So as I watched this scene my teenage lover sucked my cock. Thank God for booze and a few years on the clock. Despite being on intimate platonic terms with Mary it had been impossible not to fantasise about her and my dreams had not done her justice.

Mary was a beautifully built redhead with the blue eyes and freckles to go with it. Her breasts were those of a woman in her thirties round and firn but with the hint of soft comfort one finds in women who are no longer girls. Her nipples were a pale brownish pink and appeared hard as diamonds. I could only guess at what was in her pants. I knew she had to be ginger but the question was whether or not she favoured any particular hairstyle. She was as I often told her a sad loss to mankind.

She would come over for a drink form time to time tell me about her affairs and we'd swap stories chew the fat sometimes she'd even snuggle up but she was a girl's girl and we both agreed that there was no hope. Once or twice after we'd drifted off to sleep together on the sofa she'd wake and tease me about my hard-on. I'd simply tell her as soon as she was gone I'd take care of it and we'd laugh it off. She once confided that she was flattered that she got me hard and felt guilty about my predicaments. Tonight she saw it in the flesh, throbbing before her.

I sent a load of my seed down Libby's throat as Angela watched. She was fascinated more than interested I suspect but I noticed an odd look in Mary's eye.

Angela's knickers were round her ankles and she had displayed her most intimate parts and moments to all of us. Mary's beautiful breasts hung in the deep "V" of her open blouse. My cock was being washed by Libby as she sucked my seed out of me for all she was worth.

I had no idea where we went from here. Between the sofas was a big area with softish rugs on it. Mary threw a few cushions down onto the floor and took Angela down with her. Completely uninhibited she began to make love to her in front of me. What surprised me was Libby's reaction. As her sister lay back and spread her legs hooking them over Mary's shoulders. Libby got down and began to undress Mary. She stroked her softly but not to the point of fondling. Firstly, off came the rest of the blouse and then as Mary knelt licking at Angela's virginal nest of pleasure Libby unbuttoned her jeans and pulled the zip down. She eased the pants over Mary's hips and bottom and exposed her panties. Mary's shoes were long gone so with a bit of gymnastics her jeans were off one leg at a time without her tongue ever leaving Angela's pink dripping open secret.

Mary's choice of panties surprised me. On her well proportioned rear sat the sweetest little pair of pink silk panties with delicate lace trim and as far as I could see a transparent lace front panel. The gusset was silken and it may have been my eyes playing tricks but it seemed moist. I would have expected the boyish cottons much favoured by athletic young women. Not so! I couldn't wait to see beneath them but Libby got up and began to disrobe indicating that I should do the same and join her. As my cock was already out it seemed a sensible thing to do. Libby lay down beside her sister and looking at me pulled her legs back and open simply saying

"Do Me" - our shorthand for my licking her.

So here we were, old friends Mary and I doing two teenage sisters on my living room rug. Life could be worse.

My cock was semi hard as I put myself between Libby's thighs. As I looked up I saw her watch her sister and extend her hand to hold hers. It was a sweet gesture. Mary's hair was all over Angela's crotch as she ate her virgin lover into a frenzy. My cock swung at half mast as I went to work on Libby.

Both girls came at the same time and their respective lovers sat back to admire their handiwork. My cock continued to fill and I knew that Mary had had no relief.

Mary was wetting her panties and I was obviously aroused. Libby was frankly drunk and so was her sister. Libby suggested I fuck Angela but I knew she liked girls and I was pretty sure sober she wouldn't have consented. The booze really hit Libby and she couldn't do anything but lie back and sigh. I even thought she might fall asleep. Mary looked longingly at Angela and sighed at the semi-comatose body she had just made oral love to.

"So it's just we old-timers" she giggled.

"Yes, but ...."

And she interrupted me.

"Well we're friends and we could leave the sleeping beauties here and have a bath and some more wine and frankly I need to relax and get some relief. So let's go play with ourselves."

I know better than to delay when an attractive lesbian offers to masturbate in front of me.

I got up and went to get another bottle and run a bath. Mary tucked a blanket over the girls who looked so innocent as they slumbered.

I uncorked the bottle poured us both a glass and sat back to wait for Mary.

She appeared at the door smiled and walked over, dropped her panties and got in opposite me. She seemed to have an idea and reached for her silken understatements.

"Where are my manners!"

She smiled offering them to me, the clear implication be that I sniff them as I pleasured myself.

I thanked her with a grin.

"I wish I could offer more. I do love you but I haven't had a man since I was very young and I'm too out of practice and it's twenty-two years since...... you do the maths..." she trailed off sank her glass in one gulp and lunged at me.

Of course I cuddled her and kissed her, my cock pulsed against her and she fondled it slightly awkwardly.

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byRed Hugh© 1 comments/ 98288 views/ 3 favorites

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