Harry Herric and the Milfs

Jill, the Milf

Then, things changed again. My job at the estate agents wasn't in selling of course. I put up and took down the For Sale boards, I went out to properties to take photographs and prepare floor plans, but had little contact with clients beyond that. One day I went out to measure up a house we had taken on. When I got there, I recognised the woman who was selling. She had a daughter who I had fucked once. I would have been happy to keep fucking her, but it was only a week or so before she went off to university, so never had the chance.

Her mother was probably in her mid 40s, conservatively dressed. When I arrived, she let me in and went back to her phone call. She was angry with whoever was on the other end. Suddenly she erupted, screaming abuse down the phone, then slamming it down and bursting into tears. I wasn't sure what to do, but couldn't ignore a woman in tears, so went to check she was OK.

"No, I'm not," she spat. "My useless husband decided, last year, that he wanted to trade me in for a younger model. It turned out he'd been shagging this woman at work for two years and she wanted him to move in with her. That's why I'm selling. I don't need a house this size on my own. When Penny comes home it won't be for long. Now he's apparently split up with her and wants to come back. Fat chance. Why do men of a certain age try to get their youth back by shagging younger women? Women don't do that, although, maybe we should."

She looked me up and down.

"I know you, don't I. You took Penny out once. You probably shagged her too, if the stories about you are right. Good for her."

I could hear her brain racing.

"I remember now. You were shagging Ann Wilson and her mother Judith, as well. I can't blame you. They are both hot stuff, although Judith has settled down now I hear."

There wasn't much I could say to that, so I said nothing.

She looked at me appraisingly.

"All the stories I hear about you suggest you are a bit of hot stuff yourself. You seem to have the knack of giving women a lot of pleasure."

She paused.

"I'm going to be blunt with you. I haven't had a decent shag in years. Even before he decided to move on to a younger model he wasn't very good at it. God knows what she sees in him. I know I don't compare in looks to Judith or Ann, but I'm still in good shape. How about a quick shag now?"

By now she had me pinned against the cupboards in the kitchen. To be honest I wasn't averse to the idea, but I had a schedule and it would be noticed if I was very late. I was also a bit nervous about fucking someone already so stressed out and perhaps not exercising her best judgment.

"Look, I don't think that would be a good idea at the moment. You are stressed out and I don't want to take the risk of you changing your mind halfway through."

She pulled back, her face crumpling.

"It's OK, you don't have to let me down gently. You don't fancy it with an old bag like me."

"No, that's not it. I just don't want to take the risk of being accused of rape or something if you were to change your mind. If you still think the same when you have cooled down, you can ring me at the agency."

After assuring her I meant what I said, she let me get on with my work. That didn't stop me checking her out when I got the chance. I could see she moved well, even elegantly. She seemed to have a good figure, although the loose fitting blouse she was wearing made that hard to tell. Her skirt though was tight across a nice, firm, backside.

Abby, the yummy mummy

If that wasn't enough, at another job the next day, I had the same problem. This woman, she told me to call her Abby, Mrs made her feel ancient, was not much older than me, perhaps mid-20s. She was pretty with huge breasts. I thought she'd had a boob job until I saw a tiny baby in a crib. She had obviously been crying with red-rimmed eyes. She carried on sobbing as I went round the house measuring up. I couldn't stand it in the end, and went to ask her if there was anything I could do.

Unfortunately that sent her over the edge and she completely broke down, sending her baby off too.

"She needs feeding," she said and without any warning she pulled up her shirt and put the baby to her breast. The child eventually stopped sucking and began to cry again.

"It's OK little one," she cooed, "just give me time to swap over."

With that she pulled out the other breast and the child contentedly settled down again.

I'd seen women breast feeding before, but usually they took pains to cover up. Abby just ignored me. At last the baby was content and fell asleep almost immediately she was put back in the crib. Unselfconsciously, Abby tucked her breasts away again and pulled down her shirt.

"Bill can't stand to watch me do that. He thinks it's gross. I think watching him chew his food with his mouth open when he slouches in front of the TV is gross, but he still does it. He thinks these are gross, too" and she hefted them in her hands. "Do you think so? I don't. I like having big tits for a change."

She was still holding them and despite myself, I was beginning to stir. I tried to divert her.

"Have you got a new house in mind Mrs, I mean Abby." Unfortunately that triggered another flood of tears.

"I'm moving back with Mum," she squalled. "The little shit says I've let myself go and he's found himself some scrawny bitch. I'm not fat am I?"

Seeing her so desperately unhappy, I put my arms around her and hugged her.

"No Abby, you are far from fat. He's a fool."

She snuggled deeper into my arms. She wasn't fat, but her ample boobs were pressing into me. By now my response was obvious. She looked up at me, smiling, her eyes still wet.

"I can see I don't repulse you. It's nice to be held. Bill's the one going to seed you know. He's got a beer belly already. He probably hasn't seen his own cock in years except in the mirror."

"You know it feels wonderful when I feed the baby. It's bordering on the erotic. I offered him a taste once. He acted as if I was giving him the contents of her nappy. He stopped fucking me once I started showing and he hasn't been near me since. You would like to taste them wouldn't you. I want you to."

That almost pushed me over the edge. I stepped back and held her shoulders.

"Abby. Stop and think. Of course I'm not repulsed by you. You are a beautiful sexy woman. But you are upset, your husband has dumped you with a tiny baby and you are moving back in with your mother. You don't want to do anything that might complicate your situation any more than it is. You don't want to give him ammunition, and I certainly don't want to be that ammunition."

She smiled then, for the first time, but it was not a nice smile.

"You needn't worry about that. My grandmother owns the house. I'm moving back to live with Mum so she can help me with the baby once I go back to work. Granny is letting it for now and putting any profits into a trust for the baby."

She backed off and stepped out of her skirt. Very quickly she was naked, holding her swollen breasts in her hands. Then, taking my hand she led me through into her bedroom.

"I'm not ready to have anyone else inside me yet. I would let you come in my mouth, but that doesn't feel right while I'm breast feeding. You can finger fuck me though. In fact if you were to do that at the same time as you suck these, it would be heaven. Then when I'm done you can come all over them. Do you want to do that Harry?"

I didn't argue. It was stupid, and I was taking advantage of her distress, but by now I was past caring. I ripped off my shirt, dropped my trousers and extricated my aching cock from my boxers. Despite what she had just said she took me deep into her mouth, before she licked the already drooling end.

She laid back on the bed, lifting and opening her legs to me. Without delay, I buried my face between her thighs, tasting her arousal. She was already wet. With tongue and fingers, I started to play with her cunt. She came quickly. She cried out in surprise, then again as another one rolled over her. I kissed my way up her body, one hand still between her thighs, the other gently squeezing a nipple.

I took the other nipple between my lips, sucking gently. She sighed with pleasure, then as I redoubled my efforts down below she became louder. Suddenly I tasted it, her milk dripping into my mouth. Greedily, I sucked at her. Gently she moved my head to the other one, saying "Don't forget baby."

I sucked on her again and her back arched as my fingers found her clitoris and she moaned. Again the milk flowed into my mouth. I swallowed and reluctantly released her nipple. I licked along the fold on the underside of her breast, I remembered Judith in particular loved me kissing her there. I was still finger fucking her and she continued to come, one after another, not strong, but never giving her the chance to completely come down before the next one hit.

Finally, she gasped, "Please, stop."

"I want you in me Harry, somehow."

She rolled over and lifted her bum in the air.

"Do it this way. Please, I want you deep inside me."

"Are you sure?"

"No, Bill liked it, but I'm not keen. I just want to feel you inside me."

Gently I rolled her back.

"If you don't like it, don't do it. Just suck me for a bit."

She didn't need encouragement, and swallowed me in. She gagged as she tried to take my full length, before I put her hand around the base.

"I'll tell you when I'm close."

I gasped as she took my scrotum into her mouth, then licked along my full length, before taking me in again. She was getting me deeper with each bob of her head and as she did I came closer to coming.

"Now, I'm coming," I cried out desperately. She didn't stop though and I started to unload in her mouth. She pulled away, letting it drip out onto her as I pumped the rest across her swollen breasts. She took me back between her lips, biting the tip gently. I thought I was spent, but as she touched the super-sensitive end, I managed one last spurt on her tongue. She stuck it out at me to show it coated with my come before taking it back in and swallowing.

"I've got something of you inside me now," she said, lying back on the bed and massaging my come into her body. "Now I'm going to lie like this and remember it all. You made me come more this afternoon, than Bill did in our entire time together. In a few months time, when I'm ready, I want you to come back and do it properly. I want to have that cock inside me and to wrap my legs around you and keep you with me for ever."

"That's quite a testimonial."

She laughed delightedly.

"Is there something in your come that makes me happy? Or is it how you put in me that's lightened my mood? I feel so much better."

I gently kissed her.

"Abby, I still have to measure up the house."

"As long as you do it dressed like that, I don't mind. I'll just lie here and watch."

I indulged her, in fact it was quite a turn on, so much so that by the time I'd finished she was able to give me a hand job, while I dumped another load onto her chest.

"I know you have to go now, but thank you Harry. Just remember, I'm coming back for more in a couple of months."

Annabel returns, Ellen is jealous

I made the mistake of telling Angie about my encounter, although not all the details. She told Ellen, who was seriously pissed with me. I was thrown, she had never objected to me fucking Angie. Indeed Angie was a regular in her bed too. On top of that, she was always telling me I should be with girls my own age. I had read that as giving me some freedom. I was wrong though. She acted as if her anger was because Abby was married, but it seemed more than that.

The next few weeks were relatively quiet. I didn't want to upset Ellen, so I restricted my sexual activity in general to her. I did finger fuck Angie one night when the place was empty. She was getting on well with Gerry, but kept coming back to me for what she called a 'top-up'. Apparently he was getting better, but she was also getting more demanding and he couldn't always keep up with her.

Then my quiet spell was over. Jill, the woman who's husband had left her for a younger model, rang me at the office.

"I'm not angry or upset now," she said. "Come over tonight."

Of course I did. When I got there, she almost dragged me into the house, before she was all over me,

"Harry, I'm not looking for finesse tonight, nor tenderness. All I want from you tonight is raw sex. I want to feel as if I'm so desirable you can't wait, you can't control yourself. I want to be used, so use me."

I've never been turned on by pretend 'dirty talk', but this was no pretence. My body knew it, even if my mind resisted the idea. I had an erection before I'd finished undressing, but her openness, her vulnerability as she told me what she wanted, soon turned that into a raging throbbing hard on, that threatened to overpower me, let alone her. She looked at it in fascination as I walked towards her, pushing her backwards onto the bed.

I lifted her legs up, and over my shoulders, lifting up her wet and ready cunt. I drove into her without waiting. I was relentless, pounding at her. I was past any concern for her, all I could feel was my cock, still hard as I fucked her, harder and harder. I was looking into her eyes, and could see them glazing over with the intensity, the ferociousness of what I was doing. I don't know if she came or not, it never occurred to me to care. Suddenly I came, pumping out what felt like huge quantities of semen. I stayed hard though and so kept pounding. The sensation now was almost painful, but I couldn't stop. Finally I had to and rolled off her, exhausted.

Once I recovered, I became concerned for how roughly I had treated her, even though that was what she had said she wanted. I leant on one elbow to check her. Her eyes were closed and she was breathing hard. I touched her cheek and her eyes flickered open.

"Fuck me, Harry, how do your girlfriends cope with that? It felt as if I was going to burst."

"I'm not always so aggressive."

"I'm not complaining, but my heart is pounding and I'm sure I went blind at one point. Harry, that was a phenomenal fuck. If I never have another cock in me, I'll remember this one."

"Next time I'll be much gentler."

"Next time! My husband never got near a tenth of that and it took him a week to recover."

"Give me an hour or so and we'll see."

She laughed. "Optimist!", but I was pretty close. It didn't hurt, that she then brought herself off by humping against my thigh then spent ages exploring my body with her hands and lips. I don't think there was a part of me she didn't caress, from my face to my feet. If you've never had your big toe sucked as if it was your cock, I can highly recommend it. In fact it seemed to provide the last bit of stimulus I needed to make me fully erect again.

"You get on top of me this time," I said, "then you can control the pace."

She climbed onto me, sitting astride, cowgirl fashion and started. I like that position, because I could see so much, my cock appearing and disappearing as she bounced enthusiastically, her breasts, bouncing and bobbing around in their own rhythm, the changes in her facial expression as she fucked me and started to come, which she did several times. Normally on my second go, I can last for ages, but she was determined to get me off as quickly as she could. When I came it seemed to go on for ever though and I could see everything leaking back down. Finally, exhausted, she collapsed across me. I wrapped my arms around her and held her in place, keeping myself inside her as long as I could.

She rested her chin on my chest, looking up at me.

"There's still a bit of go in this old gal, eh"

I kissed the top of her head.

"From what I've seen a woman's age doesn't mean relevant when it comes to a good fuck."

"I think Judith is a bit of an exception though, don't you think?"

"These last few months, most of the women I've been with have been older than me. I got propositioned by one a while back who must have been close to 60."

"From the way you put it, you turned her down though."

"Only because she was drunk and like you when you were angry, I didn't want her changing her mind."

She propped herself on her elbows and looked at me in surprise.

"You're what, 20, and you are telling me you would have fucked a woman almost 40 years older."

"She was a good looking woman, still with a great body and she was honest about what she was after from me, so yes, probably."

"Are all 20 year olds like you?"

"I don't think I'm typical."

"Shame, most of Penny's old boyfriends are still around."

"I'm not saying they would turn you down, but you would probably get talked about a lot. I don't talk about the women I fuck."

"Good for you. Now, can you manage another one do you think?"

I finally left her about 2.30 in the morning. I finally had to admit defeat, but she still wouldn't let me go until I had made her come with my tongue and fingers. I didn't tell Angie or Ellen this time, just said I'd got drunk with a couple of friends and fallen asleep on their sofa. I don't know if they believed me, or just chose to act as if they did.

I expected Jill, like Abby to be back for more in the future, but in the end, everything changed in ways I could never have anticipated. I was working behind the bar at the cafe, when Annabel walked in, with another woman about her age. She saw me and her face split into a wide grin.

"Well, of all the gin joints in all the world, I had to walk into yours. Is this the new job you told me about?"

"One of them. I also work round the corner for Tailor and Whyte, the Estate Agency."

"Sara, this is the young man I told you about."

I was given a very predatory once over by Sara. She was tall, almost as tall as me, with a shock of grey curly hair. She was wearing very tight trousers which showed off an amazing arse, with a sleeveless top, cut very low. Her arms were smooth and well defined. All in all despite her age she was a real head-turner. I saw a smile flicker across Annabel's face when she saw me giving her friend the once-over. Sara saw it too, but seemed to take it as her due.

Annabel intrigued me. I'd always though of Judith and Ellen as exceptions among older women, a list to which I had recently added Jill. To be fair, this was still a limited sample. Annabel wasn't overtly sexual like Judith, or indeed like her friend Sara, but she obviously still had sexual appetites. She had been very open about what she wanted from me when we last met, which always got me going. Too many of the young women I was meeting were playing coy, rather than admitting to their sexual appetite.

"So, Harry," said Sara, "how did you come to be working here. From what Annabel tells me you are aiming to go to University."

"I wasn't sure what I wanted to study. I'm still torn between art and engineering. I know the owner here, and she offered me a part time job, to top up what I earn at the estate agency. That would be OK if I was living at home, but not when I have to rent."

"So you have some nights off" said Sara. I recognised the look she was giving me as she spoke. This was a woman who knew exactly what she wanted, and at the moment it seemed to be me. I could see an amused look on Annabel's face as we talked. Ellen and Angie were watching though and Ellen especially, looked upset and angry.

As I served them over the evening, I found I liked Annabel, Sara, not so much. Like Judith and Ann, Annabel was outspoken but not self-centred. She made no effort to disguise her age, although with a good figure and clear skin she looked remarkably attractive. Her hands were the only sign.

"You know I'm a three times Grandma now. My youngest daughter, she's about your age, 20. My eldest sun has two boys and my middle son has a little girl. She's the youngest, about 5. My daughter was coming back with me but in the end she stayed in the States because her Dad is paying her college fees."