7 comments/ 33021 views/ 30 favorites Dog Walking Days By: Knotty_Boy It was the summer after my eighteenth birthday. Three years of university lay ahead, and I needed some extra cash to help see me through my student life. A job with a local building firm had been lined up through a friend of a friend of my dad's, and at six foot two and with a strong muscular physique, I was certainly cut out for carrying and fetching building supplies. The week before, however, one of the firm's most recent builds had disappeared into a fifteen foot sink hole. A freak accident no doubt, but one that had still resulted in a sudden cancellation of upcoming projects by concerned clients, and so the job fell through at the last minute, and I was left with no work over the next six weeks. I'd scoured all the classifieds in the local paper and the cards in the newsagents window. Nothing jumped out as particularly appropriate. I did notice however, quite a few ads asking for someone to walk dogs. I collected the phone numbers as I went and by the end of the day had called round and arranged to take four dogs out walking the next day. I had nothing else planned, it would get me forty quid I wouldn't otherwise have had plus I'd get four hours of walking in the fresh air on a sunny summer's day. And if it went well, I'd pop a card in those same newsagents' windows offering my services. It wasn't a fortune, but forty or fifty pounds each day, cash-in-hand, was a lot better than nothing. The next morning I was up early, as my first customer, a Mrs Mendoza, wanted her dog Mitzi, a Yorkshire Terrier, taken out at eight. She lived about a mile away from my parents, so I cycled over in the sunshine and knocked on the door at five to eight. Mrs Mendoza was an attractive, if rather offhand, woman in, I guessed, her late thirties. She was on the phone as she answered the door, and barely broke off from the conversation to hand Mitzi over to me. I had done a little research and knew there was a park about fifteen minutes walk away and when I suggested that I take Mitzi there for her walk, she just nodded and thrust the lead into my hand. At the park, I noticed lots of other dogs were off their leads. I realized that I hadn't had the conversation with Mrs Mendoza as to whether or not Mitzi was okay off her lead here. Better safe than sorry I thought and settled for a couple of circuits of the park with Mitzi on her lead and then home, thinking 'this is easy money'. The park was basically populated by joggers and dog walkers at this time in the morning. So I passed the time by ogling a few tight butts bouncing by in lycra shorts, and made a mental note that walking dogs in parks later in the day when the sunbathers were out could be an extremely rewarding way to get paid. All of a sudden my horny teenage musings were rudely interrupted by a small noisy dog, off its lead, jumping up at Mitzi. There were no prizes for guessing what was on its mind, as it jumped up behind Mitzi and started humping away. Shouting at the dog to get away, and pushing at it with my foot, I did my best to prevent any actual penetration taking place. "I'm sorry! But it's okay, he's totally harmless. He's been done!!" I heard a girl's voice shouting. I looked up and saw the most gorgeous girl, about my age, with dark shoulder length hair, big brown eyes, and fantastically firm but nicely bouncy boobs, running towards me. Panting, she grabbed hold of the noisy dog, and introduced her as Jenny. Apparently Stan, as the dog (a Jack Russell apparently) was called, had been neutered several months ago, but still liked to hump dogs. What's more, Stan and Mitzi weren't total strangers, Jenny's family living not too far from Mrs Mendoza's house, and the families knowing each other, so the two dogs regularly crossed paths. We got chatting and Jenny told me that the reason Mrs Mendoza needed help with dog walking was that her husband had walked out on her the previous week. She'd had a few affairs and wasn't discreet enough about them apparently, and he'd finally had enough. They had shared dog walking duties, Mr Mendoza doing the 8 am shift, and as I had already witnessed, she clearly had too much to do to already to walk Mitzi at that time as well. Jenny and I seemed to get on famously, and we just chatted non-stop. So much so in fact that before I knew it, it was almost nine, and I had to walk Mitzi back as fast as her little legs would carry her so as not to be late on my first booking. Before I left, Jenny said it had been great fun chatting, and that she would get her mum to put in a good word for me, and to tell Mrs Mendoza how great I had been with Mitzi. She said hopefully she'd see me again tomorrow morning, and I noticed that she had looked over her shoulder back at me after we said goodbye. Of course, the reason I had noticed this was I was doing exactly the same, checking out her ass, which was just about the cutest I'd ever seen. As I walked back with Mitzi, I just thought about Jenny, how beautiful she was, how well we'd got on, and how desperately I'd love to fuck her. Dropping Mitzi back home, I took a closer look at her owner, now that I knew what I did about her and the clearly passionate nature that lay beneath that brusque exterior. She'd had a chance to do her hair and make up, and I upgraded her from attractive to hot, definitely a milf. She had longish jet black hair, big sexy eyes and full red lips. She was still bloody rude, though. We chatted very briefly and agreed that I would take Mitzi for a walk every day for the rest of the week. I didn't even mind her rudeness as it would mean I'd get to see Jenny again. -x-x-x-x-x- My next booking that day was a Mrs Laing, at noon. At ten to twelve I was cycling along a street lined by lots of very large houses, and number forty seven, the address I was visiting, was bigger than most. I cycled down the gravel drive and leaned my bike against a tall tree, then walked into the porch and pressed the door bell. A stunning woman in her early forties or thereabouts opened the door and introduced herself as Vanessa. She took me through to the living room and offered me a cold drink. While she disappeared into the kitchen to get me a lemonade, I had a quick look at some of the many photographs around the walls and on the mantlepiece. There were some of Vanessa as she looked now, with a chap who looked quite a bit older than her, a posh City type, always in striped shirts and braces. There were lots of others too from when she was younger, including the odd swimsuit shot. My guess was she was an ex-model who had married some older guy for his cash. She came back into the room, handed me the drink and motioned for me to sit next to her on the sofa. She asked me about my dog walking experience, how long I'd been doing it, how many dogs I walked, that sort of thing. She seemed to be sizing me up, I guess you don't want to be handing over your beloved pet to just anyone. Well, Mrs Mendoza obviously had no problem doing that, but someone like Vanessa (as she insisted on being called) was clearly a different kind of person. She also explained that it might just be the one walk. She had a neighbour who normally took Bobby (a lively King Charles Spaniel running excitedly around our feet) for midday walkies with her own dog, but the neighbour was on holiday this week. She could probably do the other days this week herself but had an important delivery due sometime today so had to stay in. Anyway, after I had told her a bit about me, like where in town I lived, what my parents did for a living, and about walking Mitzi this morning (leaving out the bit about lusting over Jenny!), she seemed happy enough with me, so I finished off my drink and followed her through a massive kitchen and out into the garden through some french windows. She showed me out through a garden gate and told me to come back that way too as she might well be in the garden on such a sunny day. -x-x-x-x-x- The walk with Bobby was pretty uneventful. After the excitement of bumping into Jenny, spending an hour chatting and stealing glances at her round tits and firm tanned thighs, the next hour was humdrum, but pleasant enough for paid work. We walked, on Vanessa's suggestion, along a nearby disused railway line, between rows of blackberry bushes, stopping every now and then to allow Bobby to sniff another dog's behind, of course. Unfortunately all their owners were pensioners. On the half hour we turned around and headed back. As instructed, when we arrived back at number forty seven, I went around the side of the house, and through the back gate. I hadn't noticed the first time quite how huge the garden was, I guessed at least half an acre, with high walls and lots of tall, mature trees. The french windows that led into the kitchen were open, and I took Bobby in and let him off his leash. He had a lap at his water bowl and headed straight for his bed where he curled up and closed his eyes. I called out into the house for Vanessa but no reply came back. I waited a minute then walked out into the garden and called again. "Over here. I'm over here." It seemed to be coming from a raised terrace down the garden to the left. I walked in the direction of the voice and saw some sun parasols and tables. I made my way up the steps of the terrace and there was Vanessa, lying on her front on a sunbed, in just a tiny white thong bikini bottom. Her body was lithe and toned, quite incredible for a woman her age, and I reckoned confirmed my guess about her once having been a model. "Er...we're back..." I stuttered, not too sure where to look, "Bobby's all curled up in his bed. He had lots of fun, I think." "Jolly good! Thank you so much. Just as well you took Bobby out, that delivery turned up just after you left. Now how much do I owe you," she said, looking over her shoulder at me. I couldn't see where her eyes were looking exactly as she had these large sunglasses on, but I hoped to hell she wasn't looking at the front of my shorts. Just a few moments looking at her, naked but for that thin piece of fabric running up between her beautifully round, tanned buttocks had me hard within seconds, and I was sure my cock must be clearly visible through my shorts. "Ten pounds," I said in a rather croaky voice. "Oh dear," she said as she opened her purse and peered inside it, "I could have sworn I had a tenner in here, but I've just got twenties." I was stumped. It was my first day doing this, it hadn't occurred to me that I might need change, so I had no cash at all on me, and this was likely to be a one-off job, otherwise I'd have said 'just pay me next time'. Maybe she was trying it on, seeing if I'd say 'don't bother' just because you look so fucking gorgeous lying there with virtually nothing on. "Hmmm...I guess I'll just have to give you a twenty then, seeing as it's my mistake." She pulled one out of her purse and handed it to me. "But, you know what, if you don't mind awfully, could I ask you to do one tiny little chore for that extra tenner? Would you mind rubbing some lotion on my back? I know it's a bit cheeky of me, but I've just turned over and I don't want to get burned." I could have sworn she was staring straight at my cock now as she peeked over the top of her sunglasses. She handed me some lotion and I knelt down nervously next to her and squirted some into my hands before spreading it gently onto her shoulders, massaging it in carefully, my fingers working it in to her soft skin, across her shoulder blades and up the sides of her neck. "Mmmm...thank you...you're really good at this. Make sure you spread it all over." As I worked my way down her back, my hands spread out and down her sides. They brushed briefly against her breasts where they pushed out a little at the sides, from being pressed against the sunbed, and she wiggled a little as I did so, her buttocks seeming to clench slightly. I reached her lower back and she jumped and giggled as I became a little bolder and squirted some lotion directly into the hollow of her back before spreading it outwards slowly with my fingertips, working it across her back, right up to the top of her great ass. My cock felt like it was going to rip through my shorts any moment. "Could you do backs of my legs too, sweetie? You're doing such a good job," she murmured. So I moved down to her legs, starting with her calves and working my way up, alternating from right to left leg as I went. As I reached her thighs, she parted her legs a little, I guess to make it easier for me to cream the insides of her thighs, but it also gave me a close up view of her pussy, barely covered by that skimpy thong, and I could see that her panties crotch was quite damp, a patch of wetness spreading outwards from her pussy lips. I reached her ass again and stopped. I couldn''t take eyes off that taut, round butt. "Hey, c'mon, finish the job. I don't want a burnt bum!" she said, playfully raising her ass slightly and jiggling it a little. Taking a deep breath, I squirted some more lotion on my hands and placed them gingerly on her buttocks. She let out a long, quiet moan. I started creaming her ass cheeks, and again she raised her ass a little, pushing against my massaging hands. I squirted more lotion directly onto her ass. No giggling this time, just moaning and pushing her ass up. There was no real need for any more lotion, but it felt so good touching her ass, so I kept on massaging. My fingers snaked between her buttocks, under what bikini material there was, easing them apart and spreading some lotion in there too, along her ass crack and down, my hand slipped over her smooth pussy lips. She didn't flinch or stop moaning, just kept pushing herself against me. She was all greasy and slippery now between her legs, and my fingers just slipped inside her. I was expecting her to spin around at any moment and start screaming at me, calling me a dirty little pervert. But she just spread her legs wider for me, giving me better access to her wet cunt. My fingers slid in and out of her, and her pussy muscles gripped onto them as they fucked her "Fuck me. Fuck me now, honey. I want that big cock of yours inside me!!" I couldn't believe my ears, but I wasn't going to wait for her to ask again. I pulled my shorts and pants off and climbed up on top of her. My knob pressed against her slit, and I eased myself forward and it slipped straight in. After spending the morning lusting over Jenny, it felt so good to have my cock immersed deep inside a hot, tight cunt. She was grabbing at the sides of the sunbeds, moaning loudly now into the rolled-up towel she had been using as a cushion. I grabbed her hips and started fucking her tight, slippery pussy with long firm strokes, my cock withdrawing almost all the way so just my knob was inside her, before piling back deep inside her, my hands slapping on her ass cheeks as I got faster and faster. She was clawing at the sides of the sun lounger now and screaming as I felt her cum spilling out all over my cock and as I felt her cunt muscles tightening around my cock, gripping on it like a hungry vice, I felt my balls tightening and seconds later I was spurting all my hot jizz inside her, spraying the walls of her pussy. I pulled out, and pulled my shorts back on, struggling to get them over my still hard cock. I knew that she had wanted me to fuck her but it was probably a heat of the moment thing and I guessed she'd be feeling a bit embarrassed right now about having got so carried away. Far from it however. She turned onto her side and propped her head on one arm, a huge smile on her face. "Mmmm. That was just what I needed. That delivery was so much more satisfying than the one earlier! Thank you so much, sweetheart. May I call you again when I need...I mean when Bobby needs taking for a walk?" I told her yes of course, it would be a pleasure, then explained that I had another appointment to get to, and left. -x-x-x-x-x- The rest of the afternoon went by in a blur to be honest. I hadn't been a virgin before my encounter with Vanessa, but I wasn't exactly what you'd call experienced either. Two girlfriends and fairly conventional sex in the bedroom had been my lot. Nothing as impulsive and erotic as the outdoor-sex-with-a-total-stranger I had just had with Vanessa. It had been animalistic, so visceral, and I had cum more intensely than ever before. More to the point, it had happened only a few hours after I met the gorgeous Jenny, who had dominated my thoughts that day right up until I laid my eyes on Vanessa in that thong. The feelings I had for Jenny were normal, healthy, teenage feelings. Boyfriend-girlfriend summer romance kind of feelings. Yet now, between our first meeting and our next, I had shot my load into the hot tight pussy of a woman more than twice my age whom I might never see again. An experienced woman who knew what she was doing and had blatantly seduced me. At the final moment, just as I had exploded inside Vanessa, it had been Jenny's face I had seen, her cute ass my balls were slapping against as my cock drove in. But would sex with Jenny, a girl my own age and level of experience, be as exciting in reality? My mind was in a whirl. My next booking was with another older woman, a Mrs Rawlings. She may or may not have harboured lascivious feelings towards me but it was pretty irrelevant. The reason she needed a dog walker was that she was so overweight she was incapable of walking more than a few hundred yards without getting out of breath. Her husband was able to walk Archie, their Bull Terrier, in the morning but didn't get back until late and Archie really needed a walk in the afternoon too. Archie's walk went without incidence and was just as I had expected dog walking would be, no surprise encounters with beautiful girls or outdoor sex with strangers! The last booking of the day too was pretty normal. Mrs Taylor was in her late seventies, pretty much an invalid and suffering from the early stages of dementia, according to her son, who had phoned me to arrange the booking. He wouldn't be there to meet me, being out of town at the moment, but Lily, Mrs Taylor's carer and home help was there throughout the day and would be happy to introduce me to Ruby, the Golden Retriever I was to walk. It was another big house on another posh street. Way too big for an elderly woman to be living in alone, which I guessed she did, assuming her grown up son had his own life. Maybe she had lived there most of her life though, and it would be too much of a wrench to leave now. It was Lily who answered the door. She was a very pretty Thai or maybe Filipino woman, dressed in a work tunic and slacks, I'd say mid twenties, maybe a little older. She was tiny, no more than five feet tall, and slim, but lovely and bright and chatty. Lily took me to the kitchen to make me a cold drink and to show me Ruby, who was sleeping in her bed. Ruby's walk was very different from the other dogs I'd walked that day. Like Mrs Taylor, she was clearly getting on in years herself, and was far less active, which suited me fine after a very busy first day of dog walking. We plodded along around the block, a little uphill one way and downhill on the way back. We got back home a little early but she still crawled thankfully back into bed and let out a huge sigh. Lily was busying herself in the living room but popped in to see how things had gone, and give me my money. I said I'd see her again tomorrow and headed off. That night in bed I experienced such a weird mix of feelings. A feeling of pride, in that I had maybe created a little summer holiday business for myself, hoping to get more bookings. A sense of elation at my unbelievable encounter with Vanessa. Anticipation, as I looked forward to seeing Jenny again, hoping we would get on as well as we had today and wondering if we did, should I ask her out on a date? And a little guilt - for some reason I felt I had been unfaithful to Jenny even though we'd done nothing more than chat. I drifted off to sleep expecting some very strange dreams indeed. Dog Walking Days -x-x-x-x-x- Five to eight sharp again at Mrs Mendoza's. She looked like she'd been working out in her home gym (the house was easily big enough to have one), as she answered the door in tight leggings and a loose vest top over a sports type bra. Her hair was tied back in a ponytail and she seemed quite breathless. Maybe she'd been putting a hunky young personal trainer through his paces? She led the way through to the kitchen and told me she might be out when I got back with Mitzi, and if so, that I was to give the dog her food. She caught herself as she realized she was probably asking me a bit of a favour so looked over her shoulder and flashed me a very efficient and businesslike 'thank you' smile. As she did so she probably caught me staring at her shapely ass in those leggings. Not quite as small as Jenny's, or Vanessa's even, but it was a really nice round shape, and she wiggled it perfectly in that tightly stretched fabric. I was imagining what she looked like on the step machine, wondering what her ass would look like without the leggings. And as she caught me staring, a woman like her probably knew every one of the dirty thoughts going through my head. If she did catch me, she didn't seem to mind, and just took it in her controlled stride, handed me keys and told me that she hadn't checked Mitzi's food cupboard, but if it was bare, there was more food in the utility room, down the hall from the kitchen. And off I went, dragging little Mitzi through the streets in a hurry towards the park. As soon as I was through the park gates I scanned the horizon for Jenny. I kicked myself for not having agreed a meeting place, or getting her mobile phone number. I criss-crossed the park for ten minutes, but couldn't spot her anywhere. Maybe she wasn't coming after all. Then I remembered that I was being paid to look after Mitzi and started to pay her some attention for the first time today. Mrs Mendoza had said it was fine to let her off her lead in the park, and I found a stick she seemed to love chasing. Ten minutes passed, then fifteen, as I kept checking the time. Jenny wasn't coming, it seemed. "Sorry!...I'm so sorry!...I got held up! Stan hasn't been well." She was running towards me, and she looked even better than she had yesterday. I couldn't help smiling, and my cock couldn't help twitching, when I saw what she was wearing. It was sunny, but still only half past eight in the morning, and she had on a pair of white denim cut-off shorts, and they were seriously short! On top she wore a checked shirt, the ends of which she had tied together, leaving her soft firm midriff exposed, a cute belly button piercing glinting in the sunlight. The shirt had several buttons undone, and I could see the edges of a black push-up bra that made her cleavage look out of this world. She had on high heeled wedge sandals, and all in all her outfit was far racier than was needed for an early morning dog walk!! I was delighted as she was surely making this effort for my benefit. We didn't have long together today, as she was so late. But we sat on a bench as the two dogs ran and played together I suggested we meet in this spot in future, explaining that I had walked up and down looking for her. She seemed delighted to hear this and put her hand on my leg as she said again how sorry she was for being late. I got her phone number too, so we could message each other if we were going to be late or our plans had to change and we couldn't make it. Considering how little time we had together, it was time well spent, and as we said goodbye, she lent in to give me a peck on the cheek. -x-x-x-x-x- I had three other bookings that day. Same as yesterday I had the breathless, overweight Mrs Rawlings and the elderly Mrs Taylor in the afternoon, but later this morning I had a new customer, a Mrs Coleman. I had noticed that just about all of my customers so far had been women living in large houses in upmarket streets, who were presumably well used to paying other people to do things for them, even walking their own pets. My next customer that day was quite different altogether though. Mrs Coleman lived in a normal semi detached house on an exceedingly normal street. She answered the door on crutches and it was obvious that she'd had an accident or operation on her left foot, as it was in a cast. She showed me into her living room to meet Trixie, a very cute Collie. As Mrs Coleman eased herself into her armchair, I couldn't help but notice her incredible cleavage. She was wearing a blouse with the top few buttons undone, and as she leaned forward to sit down slowl, I was able to see right down the front of it. Her huge milky white orbs hung together inside her blouse, squeezed together by a substantial but elegantly lacy black bra. They were suspended there for me to marvel at for quite a few seconds, as she evidently found it difficult to lower herself back with her injury. I suspect I failed to avert my gaze quickly enough, as though she didn't say anything, the moment she sat down and looked up at me, she looked over the tops of her glasses with a mock stern expression. She told me to sit down, and stop calling her Mrs Coleman, her name was Jilly. As was becoming quite normal now, I realised (after my atypical introduction to the dog walking business with Mrs Mendoza's offhand and disinterested manner), we had a little ten minute chat, just long enough I guess for Jilly to reassure herself that her precious Trixie would be in safe hands. She explained that some damn fool too old to drive had reversed over her foot in a supermarket car park, and that she wouldn't be able to take Trixie out for several weeks, something she was clearly quite upset about. If the first walk went okay, and me and Trixie hit it off, then she'd be wanting me to pop over every day for about a month, depending on how her recovery went. Armed with Trixie's favourite doggy treats, I set off with the bouncy little dog, following a careful sketched out route that Jilly had given me, together with a list of the other dogs we were likely to encounter, and a note as to who was friend (hang around and let them sniff each other's butts, etc), and who was foe (in particular two bigger, aggressive dogs who were to be avoided). The walk passed without incident, the two big dogs thankfully failing to make an appearance, and I chatted briefly to the owners of a few of Trixie's little friends as they nuzzled and yapped at each other. Jilly had given me a front door key to save her hobbling all the way from the back garden where she was planning on reading a book in the sunshine. I led Trixie through the house and out of the kitchen door into the garden where I unleashed her. She ran up to where Jilly was sitting, licked her owner's legs a few times, then headed off down the garden for a wrestling session with her favourite toy. Jilly heaved herself up out of the patio chair she was in and welcomed me back, asking how it had all gone. I noticed she had swapped the blouse for a dark blue vest top, which was struggling to contain those massive breasts of hers. I could see them better now, both the cleavage I had glimpsed briefly before, and their full, round shape, like two large gala melons. I had no idea about bra sizes, but I'm guessing they must have been E's or F's, or even G's. For the second time that afternoon, I think I got caught ogling her voluptuous breasts. Jilly smiled and said her purse was in the kitchen. Once in the kitchen, however, she let out a low groan of frustration. "Damn. I've left the blasted purse in my handbag upstairs," she said, "I try not to navigate those stairs more than a couple of times a day with this bloody leg." I told her not to worry, that if she was happy with me walking Trixie again tomorrow, then she could pay me then. "No, no. That's not how I like to do things. Never a borrower or a lender be, that's a very important principle I live by. You have done a good job and deserve to be paid. And paid you will be." I tried to convince her that it was really no problem at all, but she remained determined to pay me. "No, just wait a second while I summon up the energy to get up those stairs...unless...?" She was looking at me over the tops of those glasses again, only this time with quite a mischievous grin on her face. With that look and her shoulder length brown hair with a slight streak of grey, she reminded me of a sexy headmistress, thinking up some inappropriate method of punishment for one of her pupils. My cock twitched and thickened in my shorts. "Unless...how shall I put it?...unless we could come to another suitable arrangement that would satisfy both parties...that might be acceptable, yes?" Her grin broadened, and she sank down into a hardback kitchen chair, obviously easier to get onto than the armchair. She propped the crutches up against the wall and, right before my eyes, she put a hand under each huge round breast, lifting them very slightly as if weighing them. She looked down at them, then up at me, again peering over those glasses. My cock was straining at my shorts now. "Now I've noticed that you seem quite taken by my big boobs young man," that sexy school ma'am smile again, "so how about I pay you for Trixie's walk today with a really nice tit fuck? Would you like to empty all that cum you have in those balls all over my big tits? Mmmm?" Another twitch in my shorts, and a throb as a good dollop of pre-cum soaked into my pants. I stood there with my mouth open. I didn't utter a sound, nothing. I didn't need to. She could see my eyes transfixed on her breasts, and the burgeoning front of my shorts. Then she hooked a thumb under one strap of her vest top and eased it down and over her arm where it hung loose. She did the same with the other strap. Her vest top hung on her chest like a boob tube, then she eased it slowly down, over her breasts, until it was around her waist. Only that black lacy bra covered her tits now. I could see the dark pink edges of what must be huge areola peeking out from under the lacy cups. Again she put her hands under her breasts and this time jiggled them around a little for me, and ran her thumbs over her nipples. God how I wanted it to be my hands doing that. "Well, I think it's your turn in this little game of 'I'll show you mine'", she purred, "Why don't you slip those shorts down so I can get a better look at what I'm going to be squeezing in here." She rang a finger along the length of her ample cleavage. My shorts were down in seconds, I stood there with my cock standing up like a flagpole, stretching my boxers. She looked at me and raised an eyebrow. The boxers followed my shorts to my ankles and my cock sprang out, the knob glistening with sticky pre-cum. Both eyebrows were raised now, together with an appreciative smile. Then, slowly, so achingly slowly, she eased a bra strap down just as she had done with the vest top. The lace cup fell forward slightly, revealing a few more millimetres of that enticing areola, and she ran a fingernail around its circumference, just under the lace. My cock was oozing so much pre-cum now it was spilling over and hanging in a long sticky string. I grabbed hold of my cock and started to rub my knob. "Ah ah ah!" Smiling, she shook her head and wagged a finger. "Hands off that big cock of yours now, young man. You will leave that to me please!" I did as she said, just hoping that rule wouldn't apply to me handling her breasts. The other bra strap came over the shoulder, I swear even slower than the first. Fingernails tracing around both nipples now, still mostly hidden from view. Then one of those same fingernails beckoned me closer. Shorts around my ankles, I shuffled towards her and she took my cock in her right hand, wanking me slowly. Then with her left hand she eased the bra cup down over her huge left breast, exposing it entirely. The nipple she revealed was even more beautiful than I had anticipated, the areola a good two inches in diameter, with a small but wonderfully thick bud in the middle, an even darker pink, brown almost. She took my cock and pressed the knob against that nipple, rubbing it in circles around the areola, nudging it up against the bud, covering it all in shiny slippery pre-cum. Her nipple stiffened and grew under the attention, and I imagined taking that fully hard nipple in my mouth and sucking for all I was worth. But Jilly had other ideas. She pulled down her right bra cup and gave her other nipple the same treatment, moaning as that nipple too grew to its full size. Still keeping hold of my throbbing cock, she deftly unclipped her bra at the front with one hand, slid the straps off her arms and threw it to the floor. Staring me straight in the eyes, she cupped her heavy breasts, pushing them together, squeezing on her nipples with her fingers. "Now I want you to cover these in your hot sticky cum, young man. I want cum on both of my nipples so I can lick it off," and with that she lifted her right breast up to her mouth and licked slowly on her nipple. Letting go, she let her breasts hang totally free for the first time. She swung them gently, just enough to make them wobble and bounce a little. They were beautifully round and hung less than an inch apart from each other, so it actually took very little to press them snugly together. And that soft warm valley was where throbbing cock was heading right now! Jilly took my dick and, urging me to move forward again, pressed it gently into her cleavage and closed her soft breasts around. Then she dribbled a long line of saliva down between them to lubricate my cock, and she invited me to do the same. Between us we managed to coat those soft fleshy pillows with enough saliva to make them as slippery as a slide at a water park. "Right, now take my big tits in your hands, squeeze them together and fuck them nice and hard for me. Fuck them until you feel that hot cum welling up inside your heavy balls!" she instructed me. I didn't need telling twice. I grabbed hold of those huge breasts, my hands replacing hers, and pulled my cock back and down, then thrust it back up again. The feel of her soft flesh pressing in from all sides on my throbbing member was unbelievable, and seeing my knob appear up from deep within her cleavage, all slick and slimy from the spit and my copious pre-cum, was almost enough to make me cum right there and then. She put her hands on my hips to steady me. "Take it easy darling, slow down just a little, you'll last longer and it'll feel so much better when you finally shoot your load all over them," she whispered. I could see she was enjoying this as much as I was, she was looking down in between her tits, watching my cock fucking them. Every now and then she would dribble some more spit down to keep things sliding along nicely. And she kept looking up at me, smiling, urging me to keep this nice steady pace going so we could both enjoy it for as long as possible. Though I had spent many hours fantasizing about having my cock between a lovely big pair of breasts like Jilly's, it had never occurred to me that a woman would enjoy this so much. Yet here she was, loving every minute of it. I was trying my best to hold back, but even at the slower pace, the sensations were just too intense on my poor throbbing cock, the image of my cock slipping in and out too much to bear. Jilly must have sensed I was approaching orgasm, for as soon as the first jet of hot sticky white cum shot up and hit her in her throat, she whipped my cock out from between her tits with her hand, and aimed my gushing knob expertly at her nipples. I watched as one load after another of thick white goo landed on her left breast, almost covering her lovely big nipple altogether. "Now then young man, I want every last drop of that beautiful cum, don't you hold any of it back from me will you?" She said this in that mock stern voice of the sexy headmistress, and as she spoke she started to squeeze my shaft tightly as she wanked me, milking the entire contents of my balls onto her. Pointing my still spurting cock at her right breast, she managed to cover it with almost as much sticky goo as she had on her left one. Satisfied that I was fully spent, she released her grip on my cock, but not before licking the last drop of cum oozing out of the eye, and planting a soft kiss on my now hyper sensitive knob. Smiling the broadest smile I had seen from her, she used her fingertips to gently massage some of the sticky cum into her nipples. She scooped up a thick string of cum that was starting to dribble down her right breast and licked her fingers clean of it. Then she pressed her cum-covered tits together, and looked down when she let them go to see her cleavage criss-crossed with thin sticky white ribbons. She giggled as she ran her fingers through the ribbons, collecting more on her fingers for her to taste. "So much cum in those balls of yours young man, so much scrumptious, delicious cum. Now, I did promise, didn't I?" and with that she lifted her left breast to her mouth and started licking her nipple clean. "Mmmm...soooo tasty... I just love to lick my big titties clean of hot cum." Keeping her eyes on mine all the time, she then took her nipple fully in her mouth and sucked hard on it, sucking it clean. I just watched in a trance as she licked both of her titties clean. By the time she had finished there was hardly a trace of my cum left anywhere to be seen. She sat back and stretched, arching her back and spreading her arms, so those incredible breasts rose, stretched taut on her chest. "Mmmm... that was most enjoyable...most enjoyable. I can see I'm going to enjoy Trixie's walkies a lot more than I thought I was going to. Shall we say same time tomorrow?" -x-x-x-x-x- The afternoon again passed, thankfully, without too much incident. Mrs Rawlings wheezed her way to the door to deliver Archie to me, and then back again to pick him up. Lily welcomed me at Mrs Taylor's, just as bright and breezy again, and gave me a key for the back door. She had spoken to Mrs Taylor's son on the phone and told him I seemed totally trustworthy, and they agreed it was easier if I could let myself back in, as she often popped out on errands. Sure enough, Lily wasn't around on my return, so I let myself in, but Mrs Taylor was sitting in the living room. I introduced myself but she seemed totally confused, and appeared to think that I was her son, which was a bit difficult. She kept nagging at me to do something about the back fence. In the end I played along with it and said I would deal with it. I just hoped Lily would be there again in future. I received a text message from Jenny at about six, saying she'd be there at eight on the dot the next day and apologising again for being late. My cock got hard thinking about her in those tight little shorts, which was amazing given my balls had been so comprehensively drained earlier in the day. Then about twenty minutes later I had another text. From Vanessa. Saying that 'Bobby was starting to feel a little frisky again' and when could we arrange another walk to calm him down? I was so confused. Jenny seemed keen on me, but I wasn't 100% sure how she felt, and these older women seemed intent on throwing themselves at me, just so horny for cock. And what they had to offer, their experience and sexual know-how, was just incredible. For the second night in a row I went to sleep feeling so very excited and yet a little troubled. -x-x-x-x-x- I woke up with the most incredible hard on. What did today hold in store for me? Another early morning flirtation with Jenny no doubt. Would Jilly be hankering to empty my cock all over her incredible tits again? And what about the stunning Vanessa? She was after a repeat performance already it seemed. I hadn't replied to her text yet. I had decided to see how things went with Jenny this morning before I got back to her. I cycled down to Mrs Mendoza's feeling happy and horny. Even her normal offhand and bossy demeanour couldn't upset me. No gym gear this morning, she seemed in business bitch mode already, make up all done and wearing a blouse, mini skirt and heels. She did look damn hot, I had to admit, but I had other women on my mind. Two others who definitely wanted my cum, and another who hopefully did. Dog Walking Days I got to the park, sat on the bench and waited. Jenny hadn't texted to say she'd be late, but she was clearly going to be. I watched as Mitzi happily chased the stick I was throwing somewhat half heartedly. She was also barking enthusiastically at a rather scary looking dog, quite a bit bigger than Mitzi, who was also off its lead. I was trying to work out whose dog it was, but no obvious candidate stood out. "Hi, sorry again," Jenny panted as she trotted up. She didn't seem in a particular hurry and hadn't made the same sort of effort with her appearance as yesterday. Just baggy jogging trousers and a loose t-shirt. It occurred to me that her first words whenever we had met had been some sort of apology. In the distance Mitzi was running around in circles with this big wolf hound dog, and I was starting to feel apprehensive. I said 'Hi' to Jenny and explained I needed to get Mitzi back. She had undone Stan's lead just before she reached the bench and he had hared off towards the other two dogs. By the time I reached Mitzi, she and the hound were snarling rather worryingly at each other, with Stan running in circles around them, yapping. I didn't like the look of things so waded in. I grabbed hold of Mitzi, shielding her from the scary hound dog. Thankfully it wasn't some mad rabid stray, and had some semblance of obedience as I shouted at it to 'stay!' and to 'leave!', but in the process, managed to inflict a fair bit of damage on one of my legs with its claws. I picked Mitzi up and carried her back towards the bench, Jenny running up alongside me having reclaimed Stan. The big dog ran off chasing after some other dogs, I still couldn't see any sign of an owner though. I sat down on the bench and, having tethered Mitzi to the leg of it with her lead, started to inspect the damage to my leg. It was pretty superficial but still stung quite a bit. Mainly scratches, thankfully no sign of broken skin or blood pouring out. "Oh poor you! Let me have a look!" Jenny cried as she saw my leg. She ran her fingers gently over my knee and pulled my legs apart to get a better view. Her fingers tracing around the area of the wound, whilst her other hand stayed on my thigh. "You were so brave, saving little Mitzi. Are you sure you're okay?" she cooed. The hand on my calves was touching my skin gently, checking for damage. The hand on my thigh was moving too, however. I had sustained no damage up there at all, and her eyes were focusing on my lower leg. Within moments her fingers exploring my thigh seemed to have found what they were looking for, as they ran lightly over the outline of my cock, then settled there, staying quite still as it thickened and stretched under my shorts. "Is there anything I can do to help?" she asked, still peering at my leg, but her hand resting on my ever-hardening cock. I was sure I could feel her fingers moving ever so slightly on it, squeezing it almost imperceptibly. My head was spinning. Did she know what she was up to, stroking my erection like that? Surely she did. She was crouched down, ostensibly tending to my injured leg but doing nothing to it in reality. I wasn't going to complain, of course I wasn't, but was she just teasing me? What was I meant to do? Thrust my groin at her, grab her hand in my own and push it against my hard cock? And what if I did but was misreading the situation? She'd jump up in shock and run off, screaming at me for groping her after less than two hours of time spent with her. I had made up my mind not to be such a wimp, to place my hand on top of hers, when she stood up, her fingers on my cock pulling away slowly, fingernails dragging along the shaft. "I think you need to get that looked at, just in case, sweetie. Get home and get some antiseptic cream on it at least. I've got to go now. See you tomorrow. Mwah!" Just an air kiss this time? Not even a peck on the cheek? After sitting there for ages with her hand on my cock. What the hell was going on? But the "see you tomorrow" too? So at least I hadn't done anything wrong. Maybe the girl just liked teasing. As long as it led to something I guessed there was nothing wrong with that. But if it wasn't for my exploits with Vanessa and Jilly, my balls would be seriously ready to explode by now after the last few days. Lucky I was getting them drained my these horny as hell milfs!! -x-x-x-x-x- Not unexpectedly, Mrs Mendoza was on the phone when I got back with Mitzi. She told the person on the phone to hold on, and then asked me again to feed Mitzi, as she needed to finish this call. So I went to get Mitzi's food from her normal cupboard in the kitchen, but it was bare. Of course, from yesterday's brief conversation, I knew her back up store of food was in the utility room. I found it just down the hall, and the utility room itself was as big as some people's kitchens! This is where the washing machine, dryer and chest freezer all lived, as well as several large cupboards housing groceries and presumably various supplies for the cleaners to use. I had expected the room to be pristine, like the rest of the house, but today at least it was in a bit of a mess, with a couple of large piles of clean laundry lying on the worktop, presumably ready to be taken upstairs and put away. I grabbed a bag of dry dog food and made to leave, but as I passed by the piles of laundry I couldn't help but notice that a lot of it was lingerie. Hell, looking closer, it all seemed to be lingerie! Putting the bag down I picked up something small and black and lacy from the top of a pile. Oh my God, it was the skimpiest, sexiest pair of panties I think I'd ever seen, so delicately lacy as to be see through. I held them up and pictured them on Mrs Mendoza. My cock grew an inch or more in my pants. The next thing on the pile was a sheer black teddy, and under that some sort of tiny black and purple corset, with suspenders dangling down. On the top of the next pile was a white pair of silk french knickers, under those was something made from red fishnet, I held that piece up, trying to guess what it was. It wasn't just tights or stockings, but it was so tiny, I stood there trying to imagine that stretched across her body in some way, my cock now aching, so I reached down to give it a quick rub. "What the he'll do you think you're doing! Put those down this instant!" Mrs Mendoza was screaming at me through the doorway. Her phone call had obviously finished! In shock, I dropped the red fishnet garment. Instinctively, I attempted to bend down to pick it up but winced as that sudden movement put undue pressure on my rock hard erection. I managed to pick it up with difficulty, but my reaction to the pain had clearly drawn Mrs Mendoza's attention to my groin, my shorts failing to conceal my jutting out cock. "Right, go and wait for me in the living room. I need to think what I'm going to do with you. I should probably call your parents or something," she barked at me. I went meekly into the living room, hugely embarrassed at the thought of being caught red handed rifling through her piles of scanties. But at the same time I just couldn't stop thinking about how many items of sexy lingerie there were. Dozens of different pieces, all different styles and materials. My cock was just refusing to soften, despite the situation I found myself in. Would she really call my parents? She knew my surname and where I lived so they would be easy enough to contact. But that little red fishnet thing, must have been a body stocking, God she would look incredible in that! "So, you little pervert, what are we going to do with you?" She appeared at the doorway. Holy Fuck! She had on that corset. It covered her stomach but stopped short of her breasts, so they sat proudly high on her chest, full but pert, her nipples hard, pointing upwards. The corset suspenders were attached to a pair of wide-mesh fishnet stockings, and over those she had on some black leather thigh length boots. She wore no panties, and despite everything else that was on show, I found myself staring at the small neatly trimmed patch of hair on her pussy. It was framed perfectly by the corset, stockings and boots. She strode up to me, and her hand shot to my hard cock, dragging her fingernails along its length, causing me to flinch slightly as they reached my knob and ran rather cruelly over it. To think, less than an hour earlier, Jenny's fingernails had travelled the exact same path. Only this time I suspected there was no teasing going on. And I was right. "Take these off!" She tugged at my shorts. I dutifully stepped out of my shorts but kept my boxers on. "And those. Take everything off!" she barked. I did as I was told and stripped naked, and stood there, arms by my side. She walked slowly around me, as if inspecting me as a specimen at a livestock auction. A finger trailed over my shoulder, down my back, over my buttocks, and around to my groin, before her hand took my cock in its grip. Standing back in front of me now, her other hand cupped and cradled by hanging balls. She wasn't gentle in the way she handled me, but God it felt good. "Hmmm... yes... yes I think you'll do," she said, before sitting down in an armchair and resting each leg on an arm, spreading herself wide. Then she said, "Now, panty-sniffing boy, get down here and lick me." I'd had very little experience of cunnilingus up until that point, but I was keen to try it. I got down on my knees in between her legs and, placing a hand on each of her soft inner thighs, just above her stocking tops, I started to lick at her pussy. "Stop!" Her hands reached down and held my head. I was clearly getting it badly wrong. "Slowly...and just use the tip of your tongue. You're meant to be tasting a rare delicacy, not licking your dinner plate clean of gravy!" I followed her instructions, licking her with lighter, more delicate strokes of my tongue. It seemed to be doing the trick as she started to moan appreciatively, and then reached down to hold her wet sex open for me with both hands spreading her labia. "Stick your tongue in as far as it will go," she said in a remarkably brusque tone considering how intimate we were being. I slid my tongue between her pink swollen lips, inhaling her sweet aroma and taste as I did so. "Mmmm... that feels good...now...fuck me with that tongue." I thrust my tongue in and out as fast as I could. Her panting and moaning increased and I was getting no more instructions from her, so, at the risk of being told off if I got it wrong again, I decided to try a few different things myself. I could see her shiny pink clit peeking out from under its hood, and gave that a few flicks of my tongue. She jumped and gasped when I did that, but didn't complain, which I took to be a good sign. I slipped a finger into her wet folds as I continued to lick at her clit. This combination really seemed to hit the spot and so I continued, thrusting my fingers in deeper and faster and flicking her clit more vigorously with my tongue. She was screaming now and suddenly her thighs clamped shut around my head, and I felt warm juices flowing out of her onto my hand. She stayed like that for a moment, with her legs together, my head wedged between them, then relaxed them. "Not bad. You're a quick learner. Now lie back." Still the very matter-of-fact tone of voice. I lay back on the floor and she knelt over me, straddling my thighs, her hands playing with my cock, rubbing my knob against the pussy lips I had just recently been fingering. She edged forward, lifted herself slightly and then sank down on my shaft. I looked up at her face and watched as she closed her eyes, and a small but clearly discernible smile appeared. She rested her hands on my chest and began to grind and gyrate her hips slowly. I watched as her breasts, pressed together now by her arms, bobbed up and down as her ass slapped gently against my thighs. She was riding me, using my cock to pleasure herself with little or no thought to what effect it was having on me. Except, I suspected, that she expected me to refrain from shooting my load until she had had her fun. She had cum once already but she clearly required more. For my part I was quite content to lie back and watch her fuck me like this, my only responsibilities being to enjoy it and not to cum. She seemed lost in a world of her own as she moved herself up and down my cock, and given the nature of our relationship, if you could call it that, I was happy to let her get on with it. I noticed her picking up the pace of her pussy moving up and down on me, her breathing was getting heavier, and her fingers were digging into my chest. Sure enough, a few moments later her hands left my chest altogether, clamped on to her breasts and started pulling hard on her nipples, really stretching and twisting them. Her back arched, she sat back and just pressed her pelvis down as hard as she could as she let out a long, low moan, sounding almost as if she was in pain. She clambered off me, spun round on her knees, and rested her arms on the sofa, her ass in the air. "Fuck me now. Fuck me as hard as you can," she murmured. It was as if I was simply her servant, here to do her bidding. Which of course I did. I jumped up behind her, eased my cock between those plump, pouting pussy lips, my hips driving it in as far as it would go, then grabbed hold of her full hips, and started pumping in an out of her. I admit that I was thinking of Jenny now, thinking of how much I'd love to fuck that little tease. Fuck her so fucking hard! "Harder!" she demanded, and I happily drove in even more forcefully. "Yes!...that's it...that!...ohhh...THAT!!" she screamed at me, her voice muffled somewhat by the seat cushion her face was buried in. I knew I couldn't keep this up much longer, my cock was about to explode. Luckily, that seemed just what she wanted. She raised her head and threw it back, crying "Fill me!!...fill me with your cum!!...shoot it all inside my hungry wet cunt noowwww!!" I needed no further encouragement. My cock let fly stream after stream of spunk inside her, and I just kept pumping hard into her until the spasms of my ejaculating cock subsided altogether. I fell back on the carpet and my cock slipped out of her. We both stayed where we were for a while, her kneeling against the sofa, her head buried once again between her arms, me lying exhausted on the floor, watching as my sticky white emission oozed slowly from pussy, welling up into a little pool at the opening before it overflowed and started to drop down on to the carpet. "I hope you're not just lying there watching your cum making a mess of my new carpet. You've only just got yourself back into my good books." Was there a hint of very dry humour in her voice, a little bit of playfulness? Or was she just being her normal bossy self? I didn't wait to find out. I went to grab something to clean that carpet with. -x-x-x-x-x- I literally stumbled out of Mrs Mendoza's. I had fucked her in the most unimaginably sexy way, quite possibly the best sex I had ever had in my young life, and, it suddenly struck me, I had no idea what her first name was. We weren't really on first name terms!! Still, she had seemed pleased with my performance. She'd had another business call almost immediately after we'd finished (of course she did!), so had ushered me out the back door pretty smartish, but she had given me a long passionate kiss as she did so. I couldn't help thinking about working my way through that pile of sexy lingerie with her. What's more, I now had to work out what to do about Jilly. I was due to walk Trixie in a few hours and at the end of that walk she might, quite understandably, be expecting me to allow her to perform fellatio on me or tit fuck me. I don't think I had anything left to give to be honest. And then there was Vanessa. Two days ago I'd have given my right arm to see her again. Now, well I still hadn't gotten around to replying to her text, there was so much going on. As it was, Jilly had a friend over for coffee when I returned Trixie back home, so I was spared having to make excuses, but she saw me to the door, and somehow, crutches or no crutches, managed to surreptitiously squeeze firmly on my cock whilst giving me a cheeky wink and saying "See you same time tomorrow." Mrs Rawlings and her mobility problems were beginning to be a welcome relief in the middle of a traumatic day! A simple, straightforward dog walking contract. I could do with a few more of those. I would have felt the same about Mrs Taylor had it not been for the distressing conversations I had to have with her when Lily wasn't around. This afternoon was another of those days, and while I could sneak in and out pretty easily to pick Ruby up, I felt duty bound to let someone know that she was back home, and so ensued a thoroughly confusing ten minutes as she asked me questions about her grandchildren. I texted Vanessa that evening, telling her I would love to help with 'Bobby's friskiness' and asked her when would be most convenient for her. I'd left it a while to get back but made a suitable excuse about being frantically busy with bookings, which wasn't a total lie!! I texted Jenny too, and was delighted that she replied almost instantly, saying she hoped my leg was better and that she was looking forward to seeing me again. A second text a few minutes later was a close-up selfie, just her lips, puckered in an exaggerated kiss, with the message "4 ur poor leg baby x". Another night drifting off to sleep a very confused but happy boy! -x-x-x-x-x- But Jenny didn't turn up at all the next morning. I sat on the bench that had, all too briefly, become "our spot" for near enough the full forty minutes that I spent in the park, getting up towards the end as I shook myself out of the sulk I was in to do what I was being paid to do and exercise Mitzi. Well at least if Jenny didn't want me, I reasoned, I had at least two sexy women lusting after my cock. Life could be a lot worse. Mrs Mendoza had been on the phone when I arrived to pick Mitzi up, and was on the phone too when I returned. She motioned for me to do Mitzi's food. This time there was plenty of food in the cupboard, so no trip to the utility room. Today wasn't going well. I popped my head round the door to the living room where she was busy talking about 'the critical importance of maintaining the schedule of Phase Two of the project plan' or some such nonsense. I indicated that I was off. Rather than the dismissive wave of the hand I had become used to, however, she beckoned me in, but touched her finger to her lips, telling me to stay quiet. She was wearing a businesslike outfit, jacket and skirt and heels. She pulled up her skirt to reveal hold-up stockings and a tiny pair of panties, then hooked a finger into the thong waistband of her panties and slid them down and over her thighs, talking business babble into the phone all the while. The panties fell to the floor, she stepped out of them, smoothed down her skirt, picked her panties up, and handed them to me. She thrust her tongue in my mouth and squeezed my cock, all of which lasted a few seconds of silence from her on the phone, before she resumed busting some poor bastard's balls. A quick smile and she shooed me away, me carrying her panties with me. I had a quick sniff of the panties before slipping them in my pocket. They smelled wonderfully of her sweet pussy, the gusset damp against my nose. Not for the first time this week I was utterly confused as to the meaning of a woman's actions. Was this a farewell with a fitting memento, or a little something to keep me going until next time she needed me? I was beginning not to care too much. It seemed to be coming easily enough from one direction or another, and all of it was the most mind blowing sex, so I was learning to go with the flow.