Harry Herrick's Naked Summer Pt. 01

A version of this has been posted before, but I took it down for an extensive rewrite.

Harry is a bit of a hapless hero, one to whom things happen rather than the other way around. He's easily distracted, especially by a good looking woman. Women seem drawn to him, so he gets a lot of distraction! 'Naked Summer' covers the time between his leaving school and all his friends spreading across the country to got to Unversity. Like most 19 year old males, he is as horny as hell so spends the summer getting as much sex as he can. There is a lot of sex in this story. some explicit, some less so. Harry is wanting to try everything and pretty much succeeds. Everything is in it -- first time, older woman, threesomes (MMF and MFF), a hint of incest (not acted upon), anal sex, oral sex, voyeurism. The threesomes include MM, and FF sex as well as the obvious.

Later stories will cover his first year working, and his time in a most unusual job... (No spoilers, but watch this space...)

My first time

I've never had a problem finding sexual partners. I started early, when I was still at school. It was then too that I developed my taste for older women. I really got going though a little bit later. It was mid July, my 'A' levels were over and I was done with school. I was hanging around with my friend Ann in her garden. We had been friends since we were about 8 or 9 years old. Her Dad was long gone. There had been some scandal at the school where he taught and he had disappeared from view when she was only about five. All the time I knew her, she lived with her mother in a huge house only a few streets over from me. The garden was huge too, especially for two 9 year old kids.

Even at 9 she had an 'I don't give a shit' attitude, which I was immediately attracted to. Most of the scrapes we got into in those early years were her idea, but I always seemed to catch the blame. Her pretty smile and big green eyes usually managed to give the impression of innocence without actually having to lie. She got away with a lot over the years with that smile of hers.

Despite all the usual problems of puberty we stayed friends. Her attitude to life meant she didn't get caught up in the usual angst of teenage girls. She was a great athlete too, representing the school in both athletics and football, which gave her some standing with the teenage boys independent of her being drop dead gorgeous.

We had snogged a bit over the years, but somehow it had never gone past that to dating. Neither of us had ever had proper sex. Well, technically I had, once. That was with a recently divorced friend of my mothers at a barbecue party soon after my 18th. She was drunk and started groping me, then dragged me back into the house and jumped me. I didn't know how to react, so I let her make all the running. I came very quickly, so it wasn't very satisfactory for either of us. When I came she whimpered in frustration, then pushed me away and fell asleep on the bed. I rearranged her clothing as best I could then left her to sleep it off. I told Ann about it, without saying who the woman was. Beyond that I had never got past a couple of clumsy hand jobs. Ann's experience was I think even less, although she was never short of boys trying to get into her knickers.

Now though, things were changing. She was off to University in September and we would be separated for the first time in years. I wasn't entirely sure if University was for me so I had decided to take a year out first. We were sitting in the garden talking about what lay ahead when she dropped the bombshell.

"I'm off to Cambridge in September. You'll be off working. We won't see each other for long periods. That's going to be really odd and I'll miss you, but I want to make the most of my time away from Mum's beady eyes and that means sex. I'm a virgin as you know, but I don't want to lose my virginity in some drunken fumble after a party. I want to do it carefully and deliberately with someone I trust, someone who won't send me home with my knickers in my pocket once they've got what they wanted. I'm not going to go through university closeted away.

She took a deep breath.

"Harry, will you be my first? I trust you, we get on well and you have never tried to take advantage of our closeness. In fact you have never shown any sign that you even find me attractive. I know I am, so I guess I'm not your type. Neither of us have ever been jealous have we, when we've gone out with other people? Oh god, I'm rambling on, I was just going to come out with it."

I didn't quite know how to respond. My first thought was of course, 'hell, yes!' When my brain caught up with my cock, though I realised there was a real possibility of ruining our friendship by bringing sex into it. She saw me hesitate.

"I'm sorry Harry, I've ruined things haven't I? You don't fancy me at all do you? That's why we've never gone out together."

She would have gone on but I stopped her.

"Don't be silly. I hesitated because I don't want us to stop being friends and bringing sex into it will change how we are with each other. If something goes wrong, it could ruin everything. On the other hand I've always thought you were beautiful and that hasn't stopped us being friends."

She blushed at that. I don't think I had ever mentioned her beauty.

"Thank you Harry. You are quite the hunk yourself. My friends are always asking why we've never seriously got together. I always say the same as you. Anyway, you still haven't answered me."

"Are you sure you don't want to find someone who knows what they are doing. I've told you of my solitary experience."

"No. I want someone I know I can trust. We can experiment together, it will be more fun that way. So, will you or not?"

"Of course I will. It was never in doubt. I just wanted you to be sure. I can't imagine anything would ever really come between us."

She gave a deep sigh.

"Thank God for that. I think if you had turned me down, that would have damaged our friendship even more than the risk from us fucking."

"Have you looked in a mirror? No one in their right mind would turn down an offer like that from someone who looks like you. I know you are more than your looks but Ann, you are a very beautiful young woman."

She blushed again.

"Look, next week Mum's going to be away for a couple of days. She's going to see a friend of hers, a pilot, who's only here for a couple of days before he flies out again. When she's away we can have the run of the house and garden. Come over on Thursday morning and come in the side gate. We can use the summerhouse if it's a nice day. If it works out, maybe we can keep doing it until September!"

Ann lived in a big house with an enormous garden, almost a park. There was a summerhouse at the bottom, overlooking a tiny stream, where as kids we had often paddled. It was a beautiful spot.

"Don't you have a gardener though?"

"He isn't coming next week. He's gone to see his daughter up in Edinburgh. She's expecting a baby."

I relaxed. I would be nervous enough without worrying about being caught by him.

As arranged I slipped into the garden though the side gate. I was already stiff with anticipation as I closed and locked it again behind me. I started forward towards the summerhouse. I couldn't see inside, but the doors were folded back and I could hear the unmistakeable sounds of very noisy and energetic sex. I moved around to get a better angle on the open doors, keeping myself concealed by the hedge that screened the side gate. I could see two naked figures just inside. At first I thought one of them was Ann, although I could hardly believe it was, given why I was here. I'd never seen Ann naked of course, but the smooth tanned body with long auburn hair certainly looked like her.

She was spread out face down on a pile of cushions, her backside elevated, the man behind her. All I could see was a long muscular body hammering away at the woman in front of him. He was clearly taking no prisoners but from the noises she was making she was clearly enjoying it. I stepped back out of sight.

I knew this couldn't be Ann, so I guessed it was her mother, Judith. I'd met her many times of course, but although very beautiful in her own right, she always came across as quite mumsy. I had certainly never pictured her in this situation before. I heard her cry out again as he continued smacking hard into her cheeks, the sound echoing around the garden. I could hardly walk in and ask to see Ann, so I started backing away towards the gate. Then I felt a cool hand on my arm. My heart in my mouth I turned to see her, finger to her lips.

"I'm sorry," she whispered. "I didn't know Mum was going to be home today."

She looked flushed and embarrassed. Not surprising I suppose if you suddenly find your mother having very energetic open air sex and obviously enjoying it. I looked back. He had withdrawn from her but was still kneeling. I could see his naked figure and as he turned slightly his erect penis swung gently. Judith turned to face him, then bent forward and began gently sucking and nibbling on his still hard and erect shaft. Her naked breasts were standing out proudly with no trace of sag as, hands cupped around his buttocks, she worked her lips around the exposed head of his penis, playfully licking it like an ice cream, her eyes looking up at him. I felt myself go hard as I watched.

Judith paused, laughing, then took him again into her mouth, to my amazement swallowing him deeper and deeper until his whole shaft was in, her lips pressed against his skin. He looked skywards, shuddering with pleasure as her lips wrapped tight around him, she pulled out, then back, out then back. I watched mesmerised as she alternately sucked and bit at him.

She redoubled her efforts, biting him hard, drawing him deeply into her mouth. He cried out but not in pain, then his back arched and he began thrusting back at her. I could see that he was coming -- pumping himself into her mouth, the muscles in his ass tensed. She held on tight, not letting him withdraw, sucking him down as he thrust forward then back. He sighed, a long deep sigh and I saw his body relax, the muscles softening as he spasmed one more time, then collapsed forward, holding her to him, gasping for breath.

She finally released his cock, and as he sat back on his heels, I could see it slowly softening and subsiding, the tip glistening slightly, semen stringing from it. She smiled, then reached out to touch the moist head of his cock with her fingers, before putting them to her lips, licking each in turn.

My erection was becoming almost painful as I watched them. I looked at Ann but she seemed oblivious to me. Her eyes were fixed on her mother and the man she was with. I made to pull her away, but she shook her head and continued to stare. She seemed to be as aroused as I was. Suddenly, all I could think of was doing the same with her. I imagined her slim body naked in front of me, her lips wrapped around my own erect shaft. I could see every detail -- her engorged lips as they gently caught me up, the incredible ease with which my rigid shaft slid between her lips so that they kissed my belly as she swallowed me, then pumping into her as she swallowed every drop. I was breathing hard as the fantasy image almost took over, then Ann's hand pulled on my arm again, pulling me away deeper into the shrubbery.

Once out of sight, she dropped to her knees, desperately fumbling at my belt, pulling at the zip, then yanking down my trousers and boxers in one swift movement. My cock bobbed up as she did it, banging against her cheek. She grabbed it, then with one swift motion, pulled me into her mouth. She tried hard to do as her mother had, but gagged as I went deeper. She sucked at me hungrily, biting and nipping me, her nails scratching at my back as she pulled me tightly into her face. I was almost ready to come within seconds, but tried to hang on. I began thrusting back, face fucking her, my hands behind her head, holding it in place. She slapped at my back urgently and I realised she was running out of air. I eased off and she gasped for breath before trying once again to take me all.

I was still doing my best to prolong things when I heard a voice behind me.

"Like mother like daughter I see."