Pretty Little Summer Dresses 10 Years Later

Hi all – Bob here! So, I've been married to Dawn for just under nine years now. Sorry you didn't get invited to the wedding but, as you can imagine, it was a bit of a wild affair – or at least that's what I'm told – I drank far too much and remember nothing between the speeches and waking in the morning with my arm around Dawn's waist and my cock between her thighs. Keeping my eyes shut, I moved my hand up to explore her bare breasts and gently pinch her nipples while slowly starting to rub my cock against her pussy, she moaned and then Dawn's voice from behind me said "Save some of that for me stud." As I opened my eyes, I realised I was looking at the back of Jess's head – my married life had started as it was intended to continue!

So, we got the nice big house and we are still in touch with Jess and Ashley. The house we bought has a granny annex and, as we have no use for it, we currently rent it to Emily – very handy for when we want an additional playmate. Taylor married an Irishman and moved to Dublin; we keep in touch but don't see her very often, though I hear that she still takes dogs for walks in the park! I am pleased to say that Niamh qualified as an accountant and has set up her own practice. As a little gamble I made on a start-up company paid off handsomely, I no longer need to work but I have retained a few clients, such as Gerry, just to give me something to do. I recommended Niamh to most of my clients, so her little practice is developing nicely and she comes around occasionally to express her gratitude – need I say more? Amazingly, she has even got Carol onside – apparently as long as Carol gets to eat Niamh's pussy once in a while she is, literally, a pussy cat! Amanda is a regular visitor and Madison is still very close friends with Shannon; the two of them attend the same local college on a fashion design course. After we married, Dawn started up her own interior design business, just locally at first but as her reputation grew, she deals with clients throughout the extended area. Most of her work is done from home but she occasionally has to visit places to get a feel for them before submitting her designs.

This coming weekend is one of those that Dawn will be leaving me to my own devices. The place she is travelling to is a bit remote and she is staying there for two nights, Friday and Saturday, returning on the Sunday.

Dawn has always discussed her concerns about Shannon with me, as Shannon has grown up. Her latest concern is that Shannon is all work and no play, with not even the remotest sign of a boyfriend in sight – she is now twenty years old and Dawn is desperate for her to learn to enjoy sex at a young age and not have to wait as long as Dawn did. In fact, Dawn has suggested to me that I try to seduce Shannon over the coming weekend, while she is off the scene. Dawn believes that, with my experience, I can introduce Shannon to the pleasures that she is missing. Naturally, I gladly accepted the task – Shannon has a body to die for and the thought of breaking in that virgin pussy is enough to wake Junior from his deepest sleep!

Friday morning at breakfast, as Dawn is getting ready to leave us, Shannon asks if Madison can stay that night. Dawn and I exchange looks but neither of us can come up with a reason to say no, so we agree for Madison to stop over. Plan foiled!

After Shannon and I have waved Dawn goodbye, we return to the kitchen. Shannon sat down opposite me with a concerned look on her face.

"Something troubling you, Shannon?" I asked.

She looked at me a bit sheepishly before saying, "There's something I need to ask you. I don't really know how to put it."

"You can ask me anything Shannon. If it's something you don't want your mum to know, I promise I won't tell but I can't help you unless you spill the beans," I responded.

"It's not really about me," she started, "You see, Madison has had a crush on you ever since that first holiday at the villa. I thought as we got older it would wear off, but as she has developed into a woman it just seems to have become an even bigger desire. Even worse than that, I think I love Madison, but I don't think she's gay or even bi, she only seems to have eyes for you."

I looked across the table, into those fierce blue eyes that burned a hole in my heart; tears were forming as I watched and I got up from the table to give Shannon a cuddle. She threw her arms around me and sobbed her little heart out as I stroked her hair. "If only you knew what I and your mother had planned for you this weekend," I thought.

I wiped the tears from her cheek as Shannon continued to tell me her tale of woe. She had actually asked for Madison to stay this weekend in the knowledge that her mum would be away, so that I could seduce Madison. This girl was willing to sacrifice her love so that Madison could get over her childhood crush. She hadn't mentioned it while Dawn was around as she was worried how she would react.

"Your mother is not the problem in this equation," I said to her, "she will be fine about it. I am more than happy to make Madison's dreams come true but I do need to check with Amanda first. She is a close friend of ours and I don't want to be bedding her daughter without her consent."

"Madison doesn't what her mum to know," said Shannon, in a slightly alarmed voice, "She thinks her mum would disapprove and it could cause all kinds of trouble between them."

"Shannon," I said, "there is no way this is happening without Amanda's say so. If she says no, I will ask her to not mention a word of it to Madison – hopefully, she will respect the fact that I have asked her permission first and keep our little secret. Now, off you go to college, I have an important phone call to make."

As soon as Shannon was out the door, I rang Amanda and told her of my discussion with Shannon. Amanda told me that she was aware of Madison's teenage crush on me but not that it was still on-going – she finished up by saying that Madison could not have a better teacher in the bedroom. I also informed her, in the strictest confidence, about Shannon's declaration of love for Madison which seemed to come as no surprise to her at all. She advised me that she could see it in Shannon's eyes whenever Shannon and Madison were together in Amanda's presence.

When I had put the phone down on Amanda, I dialled Dawn's mobile. She was still driving but was on hands-free.

"Hello," she said, "missing me already or have you burnt the house down."

Dawn listened intently as I recounted Shannon's chat with me to her. I also told her that I had Amanda's blessing to bed her daughter. Dawn went quiet for a moment and I thought I had incorrectly anticipated her reaction. It transpired that she was thinking of the effect on Shannon of all this.

"Bob," she said, "once you've given Madison the benefit of your experience, why not try to suggest to her that, before she commits herself to a heterosexual relationship, she should explore her sexuality and dabble with a lesbian relationship. Hopefully, that will be a good opportunity to introduce Shannon into the bedroom."

I agreed to try to follow through with Dawn's idea and we ended the call. What can I say, the day dragged! Nothing took my interest, either among the few odd jobs I had for work nor anything I could find on the box. My mind was fixated on the weekend and more importantly the night ahead. I decided to cook something myself rather than order takeaway and opted for poached salmon with a salad. I nipped to the supermarket and bought what I needed, whistling as I went round the aisles.

When the girls arrived, Shannon acted normally but I paid particular attention to Madison as she entered the door. I caught her looking at me when she thought I wasn't paying attention, it made me smile to see her eyeing me up. As I took her coat, I took in her attire; she was wearing a plain white tank-top combined with a mid-thigh mini-skirt, which showed off her legs perfectly. A pair of high heels completed the ensemble and, if I didn't know that it was me that was going to get lucky, I would have been dead jealous of the youth of today.

Shannon and Madison went through to the lounge while I went to the kitchen, returning with three glasses of wine. As I entered the room, I couldn't help my eyes wandering up the length of Madison's legs, to the hem of her skirt. The way she was sitting with her thighs slightly apart allowed me a glimpse of what I believed were a pair of white knickers.

"Oh, I don't usually drink," said Madison, as I offered her a glass.

"Oh come on Mad," said Shannon, "it's the start of the weekend – let's wind-down."

I noticed Shannon wink at Madison as she spoke and Madison glanced at me before her eyes travelled down to my crotch. It was all I could do to restrain myself from stroking Junior through my trousers, I was so turned on.

I chose to sit on the seat opposite Madison so that my eyes could continue to feast on her legs as I sipped at my wine. Shannon was sipping hers as well but Madison was taking gulps – if she wasn't careful she would be pie-eyed before dinner and that was no good to anyone. We chatted about how their day had been, briefly covered why Dawn was absent for the weekend which gave me the opportunity to drop in how lonely I would be in bed. The "discreet" nudge that Shannon gave Madison could probably have been seen from outer space, but I pretended not to notice. I did, however, notice the big smile and hot flush that passed over Madison's face. I went to the kitchen to replenish our glasses but gave Madison a watered-down glass this time; I wanted her to remember the night that lay ahead. We chatted some more before going through to the dining room for dinner.

At the table, I sat Shannon and Madison opposite each other and sat next to Madison. With the food served, I placed my napkin on my lap and moved my hand across to Madison's thigh, giving it a quick gentle squeeze, before returning my hand to the table. From the look on Shannon's face, she had seen everything – a small smile appeared on her face which quickly disappeared. Madison looked sideways at me and gave me a big smile; her hands dropped to her lap and she hitched her skirt up even shorter. Now I could clearly see the crotch of her panties; my gaze transfixed.

"You alright Bob," asked Shannon, a smirk appearing on her face.

My attention was brought back to the meal and I managed to finish my food, snatching glances at Madison's thighs and the target for my affections later. Madison was clearly aware of the effect she was having on me, her hands occasionally dropping to her lap and running her fingers along her thighs towards her knickers. I couldn't wait for the meal to be over!

When we had finished, Shannon suggested we watch a chick flick together. Normally that would have been my cue to go to my den but I fancied sitting in the semi-dark with Madison tonight, hoping that a little touchy feely might occur. Shannon chose to put on "Friends with Benefits" and sat down at one end of the couch with Madison next to her. I placed myself next to Madison, pressed tight up against her and dimmed the lights. Shannon concentrated on the film as I put my arm around Madison, putting my mouth up against her ear.

I had a little nibble on her ear, before whispering, "Would you like to share my bed tonight?"

I watched as her thighs visibly squeezed together; she gave a quick nod "Yes", glancing in Shannon's direction to check whether she had seen or heard anything. One hand was now around Madison, gently caressing the side of her breast through her thin top, the other was resting on the top of her thigh, a mere couple of inches away from her mound, gently stroking her skin. When the film came too the bedroom scene, Madison parted her thighs and my hand slipped in between. Her knickers were already wet and my finger caressing her gap only made them wetter.

I whispered in her ear, "Follow me," and got up, walking towards the stairs.

She glanced at Shannon, whose gaze was fixed to the screen, and got up and followed me. I watched as she walked towards me and saw Shannon glance in our direction and wink at me. I took Madison's hand in mine and led her up the stairs, squeezing her fingers with mine. Once we entered the bedroom, I said to her, "Are you sure you want to do this?"

She placed her arms around my neck and gave me a kiss full on the lips. My tongue licked against her lips until she parted them and then invaded her mouth, claiming its territory. She tasted sweet, like strawberries, and I wanted more. My hands took hold of the sides of her tank top and pulled it slowly up her body and over her head. I took a step back to admire the view; her breasts were encased in a white lace push-up bra, the tops of her breasts spilling out of the top of the cups. I bent down and kissed each breast tenderly, before reaching behind her back and unclasping her bra. I let it fall to the floor and took each breast in my hand in turn, sucking on the nipples and delighting in their response. Madison was moaning as my tongue lapped at her breasts, her hands pulling my head towards her. My hands moved to her skirt and I undid two buttons, followed by the zip. She moved her hips sensually as her skirt slipped down her thighs; my gaze captured by the little white panties with the wet patch. I knelt down on the floor and placed my lips up against her pussy, applying a little pressure as I kissed her there. Her moans were becoming louder and louder as I licked her panties before pulling the crotch to one side and attacking her bare flesh. She gasped and a stream of juice flowed from her into my eager mouth.

I rose up from the floor and guided Maddy to the bed, where she got on the bed on her hands and knees; the view of her arse was a picture and I ripped my clothes off as fast as I could, before clambering on the bed beside her. I lay on my side next to her and kissed her lips as my left hand massaged her breasts. She started to moan again as I continued to explore her body; her tongue was exploring my mouth but she had still made no move to touch my cock. It occurred to me that she might not know what to do so I took her hand and placed it around Junior, clasping her fingers closed. Her eyes grew wide as she felt it for the first time and I then started to move her hand up and down my shaft. As some pre-cum appeared on the tip, I moved a couple of her fingers to it and helped her to smear it over my knob. I then took her fingers and presented them to her mouth; she looked at me quizzically but opened her mouth as I probed her lips with her own fingers.

"Lick them," I said.

She licked the pre-cum off of her fingers and then returned them to my cock for more.

"You could always cut out the middle man," I suggested.

She looked at me with a puzzled expression on her face. I rose onto my knees and presented my cock to her mouth. She looked into my eyes as she stuck her tongue out and licked the latest drop of pre-cum from the tip. I pushed forward with my cock and she got the message, opening her mouth and accepting my cock as I pressed forward. As she engulfed my cock, I massaged her breasts before dropping my hand in between her thighs and stroking her pussy. She spread her thighs further apart, allowing me all the access I needed. I inserted a finger into her virgin pussy, slowly finger fucking her, before adding a second finger. Her pussy was wet but still tight and I couldn't wait to get my cock inside her. I extracted it from her mouth and climbed on top of her, my cock was at the entrance to heaven and I had to look down between her legs before I completed her initiation. It was such a hot view; a twenty-year-old virgin pussy with my cock at the gates, ready to invade and conquer. Junior twitched while waiting.

"Maddy," I said, "are you really still a virgin?"

She nodded. "Been saving myself for this moment," she purred.

"It is going to hurt at first – just be aware of that – but pretty soon it should start to feel heavenly," I told her.

I slowly pushed my tip into her, feeling the resistance of her hymen. That part of the female anatomy had to be given by a man – it's like "Hi men – welcome to my vagina!" As I pushed harder, I could see the look of concentration on Maddy's face, she was biting her bottom lip and a tear was forming in the corner of her eye. I brushed her cheek as I broke through and she gave out a little yelp of pain. Once I had broken through, I rested for a while allowing her young pussy to get used to its first invader. I then started to push further into her.

"It feels so big," she said.

"And you, my lovely girl, feel so deliciously tight," I responded.

After feeding her pussy my full length I rested again, enjoying the feeling of a tight young pussy. The last pussy I can remember being this tight was Niamh's, all those years ago. Madison was different; I had watched her grow up, watched her body develop into womanhood, lusted after her tits for a few years now and here I was, ready to fill her with my seed. That thought brought me to a sudden realisation – no protection!

"Maddy," I asked, almost in a panic, "are you on contraception?"

"Yes, daddy," she responded, "You don't mind if I call you daddy, do you? Mummy made me go on the pill as soon as I turned 14 – she said you can never be too careful."

"Oh Maddy – that is such a turn-on – you calling me daddy. Do you wish you were doing this with your own dad?"

"I never really knew him," she answered, panting as I began to move inside her, "I've always imagined you being my daddy and taking me to your villa and playing with me. Whenever I masturbate, it is always with you in my mind and how this would feel!"

I was withdrawing my cock and pushing it back in very slowly, I could tell Maddy was getting used to having it inside her – a smile crept across her face.

"This feels better than I ever imagined," she said.

Knowing that she was now used to the size of me inside her, I picked up the pace, pounding into her sweet pussy as I looked down on her face. Her eyes gazed into mine as she spread her thighs further apart, if I looked between her legs I could see my cock pistoning in and out of her – it was too much for me and I shot my first load (hopefully of many) into her young pussy. I collapsed on top of her and kissed her cheek.

"That was amazing," said Madison, reaching her hand down and feeling my cock still inside her. I pulled out and rolled over as she pushed a couple of fingers into her newly christened pussy, watching as her fingers explored inside her. When she pulled them out, they were coated in cum and she examined them.

"Put them in your mouth," I suggested.

She slowly, almost teasingly, moved her fingers towards her mouth, but instead of putting them in, she poked her tongue out and licked the length of them, her eyes staring at me as she did. I groaned and offered her my cock, groaning more as she lowered her mouth and opened her lips. The feel of her hot mouth and tongue cleaning my cock of our combined juices was fantastic. When she had finished, I lay her back on the bed and suckled on her tits enjoying the feeling of the soft tit-flesh in my mouth. She moaned softly, as my tongue continued to coat her boobs, my left hand reaching between her thighs and feeling the wet exiting her lips. I poked a couple of fingers into her pussy, coating them with my cum and bringing them up to her mouth. She lapped at them hungrily; she was proving to be everything I had hoped for.

I was just about to turn her over and get her into doggy position when there was a knock on the door. I quickly turned over as Shannon walked in.

"Just came in to say goodnight," she said, smiling at us both.

"Thanks so much for arranging this," said Maddy, "You helped my dream come true. If there's ever anything I can do for you, just ask."