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Harry Herrick's "Naked Summer" Part 4

New experiences for Harry - group sex with a MILF, threesomes involving both men and women, and oral sex with other men.

Spankmasters
May 22, 2024
17 min read
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Harry Herrick's Naked Summer Pt. 04
Harry Herrick's Naked Summer Pt. 04

Harry Herrick's "Naked Summer" Part 4

The first time I encountered a stepmom couldn't talk but moaned as she squeezed my balls tightly in her hand.

"I can tell what you've been up to, Harry. Listening to you and Ann upstairs made me incredibly horny. It's my turn now. Do you want to fuck me, Harry?"

She still had a firm grip on my balls, so all I could do was gasp. She loosened it slightly.

"I said, do you want to fuck me, Harry?"

"I'm sure it would be fun, yes."

"That's good to know, because I certainly feel like fucking you right now. Remember what I said about hurting Ann?"

I nodded, wondering if she really meant it.

"Well if she finds out, she'll be hurt. So this will be our secret, huh?"

Another tight squeeze and an anxious nod from me. She scared me, but she was also turning me on. My dick started to harden, even though I'd had an energetic session with Ann less than an hour ago. She looked down at my rocks and noticed.

"Yeah, I can see why she liked the look of it. Fully covered but still exposed. Take 'em off now, though."

I didn't argue. I didn't think I had much choice. I tried to keep my boxers in my pants, but she saw.

"Are you going home in my underwear?"

"I couldn't find mine, so Ann gave them to me. She liked me in them."

She nodded, came back around, and carefully lifted my skirt. Then she cupped my butt and ran her hands down my back. I felt goosebumps on my skin. After a while, she stepped in front of me and looked at me. My erection was now standing completely vertical. She pinched and pulled my shaft.

"I love young, hard cocks. They react so quickly. How many times have you come today, Harry?"

"Four. I didn't want to be too fast with her, so I took care of it before I came over."

"Four? And you're ready for more. Go and sit over there."

I obeyed, stood in the middle of the room naked except for my boxers. The room was a gym, and she instructed me to sit on what seemed like a low bench. I lay down with my legs astride and my back along the bench, and she kneeled in front of me.

"Now just lie there and fantasize about your country."

Suddenly, she bent down and took off the clamps from the bench. She tied my legs in place, then grabbed my arms, pulled them up over my head, and fastened them behind me. I was completely immobile.

"Here's the thing, Harry," she said, lifting up her skirt to her waist, "you might think you're going to fuck me, but you're wrong. I'm fucking you. I'll take whatever I want from you, whenever I want it. The only thing you have to do is keep that cock of yours hard."

It was, even getting more excited the more she pushed her limits. Then she stood at my feet, adjusting her position. She picked up some clamps from the bench and fastened my legs in place, then grabbed my arms and fastened them behind me. I was completely unable to move.

"The thing is, Harry," she said, bending beside me, "you thought you were going to fuck me, but you were wrong. I'm fucking you. I'm going to take what I want, when I want it. Your only job is to keep your cock hard."

It was, if anything, getting even more rigid. She looked me up and down. My cock was now straight up. She straddled my body and slowly lowered herself onto my cock.

"Just lie there and dream about home."

After a short moment, she began to work her muscles. I hadn't imagined someone with so much control before. At times, it felt as if she was squeezing the entire cock with a vise from the tip to the base, almost painfully. Other times, she'd put pressure on the tip and the sensation would travel down the length and back up. As time passed, she started moving her hips. When she had my full length clamped, if she bounced up, she took me with her. Then she'd release and I would go limp, to be clamped again. Picture

On multiple occasions, I was on the verge of climaxing, but she always spotted it and would grip the tip so tightly that I would start to falter, prompting her to start anew. This went on four or five times, making me suffer greatly while trapped in her control. Surprisingly, she didn't appear interested in reaching an orgasm of her own despite enjoying her power over me. Eventually, she relented and took me into her mouth instead, swallowing my whole length, just as I had seen her do before. As soon as I climaxed for the fifth time that day, the torrent of semen seemed to continue endlessly, yet she was able to swallow it all with ease. Finally, she stood up, pulled her skirt back in place, released me from her grip, and left me dazed, unable to even stand properly.

The following morning, I could hardly move due to the extreme soreness in my hips and shoulders. It took a long, hot shower to regain my mobility. My parents were both at work, so I called Ann. Judith answered and then handed me the phone. Ann didn't comment on my late-night stay, so she would come to my place that afternoon to avoid any problems with my parents.

Ann arrived quickly, and within a short time, we found ourselves in bed, hugging each other after having a rapid yet enjoyable sexual encounter. I deliberated over how to mention Judith's unexpected detention of me as I walked home. Ultimately, I opted for a cowardly approach and said nothing. An hour later, with her lips tightly wrapped around my penis and my tongue probing her vagina, I decided to keep that approach.

We took a break to have lunch and replenish fluids. I had already engaged in sexual activity seven times within 48 hours and anticipated more, so I needed to stay hydrated.

The third time was exceptional. I didn't have to worry about coming prematurely; we were becoming accustomed to each other's bodies, and there was a sense of calm about the whole experience. We explored different positions, but eventually found ourselves with me lying behind her, my arms embracing her breasts while I gently entered her from behind as she raised her leg to allow me access. My body was pressed against her back, my buttocks colliding with her groin, our skin touching everywhere possible. Eventually, I climaxed and she did as well, experiencing a gentle, gradual buildup at first, followed by an intense urgency that drove me to thrust hard and deep, bringing us both to climax simultaneously.

We remained entwined for what felt like hours. However, I soon became aroused again. We separated, and Ann knelt up to allow me to penetrate her from behind like the day before. While it took some effort to align ourselves properly, I was eventually able to lose control completely, pounding ferociously, grunting while pushing deeper with every thrust. Ann responded with equal intensity, pushing back onto me, demanding more, until eventually, I could no longer contain myself and climaxed once more. She fell forward then rolled on her back.

"You nailed it this time," she smiled triumphantly. "Twice."

I fell alongside her.

"Thank you."

"We need to hurry. Mum will be home shortly," she said.

"Let's go to your house. I want to try again if you can handle it."

I was uneasy.

"Will your Mum be there?"

"Yes, but she won't mind. You know that."

"I'm still not comfortable with the idea of being naked in front of her, though, especially with my erection - I told you I wouldn't be able to avoid one with the two of you around."

"I don't care," she replied. "I'll attach a dog leash to it and lead you around by it, so she knows you are mine."

I sighed.

"That picture isn't attractive."

She chuckled and kissed my slowly growing erection.

"It wasn't meant to be."

We began to dress, and after changing the sheets on the bed and washing them, we drove to Ann's home.

"Perhaps we can sneak in without her noticing; she may be sunbathing in the garden."

"I hope so," I replied, though I couldn't help but picture Judith's naked body sunbathing, smeared with sunscreen. "I hope she doesn't ask me to apply sunscreen on her breasts."

Ann burst into laughter.

"You would love nothing more than to smear sunscreen all over those big, round boobs," she teased.

She grabbed my groin.

"It's not just sunscreen that's tempting," she said.

"Hey, listen, if she shows interest in you," she said, "you have two options. You can tell her you're not interested, which is a lie, or you can accept that she's a wild animal and whatever happens, happens. As long as I can keep messing with you like we've been the past two days, I'm good. What I won't do, though, is be there with the two of you. That would be too weird."

She stopped for a moment, "If I decide to collect my present with Stewart, I want you there too. Imagine me sucking your cock while he fucks me like he did with Mum. It's turning me on just thinking about it."

"I'm not sure what to say to that."

"Come on."

"Okay, I'll let you know. In the meantime, we need to handle the immediate issue of your mother. We'll be there soon. It's not that I don't find her attractive, she is, for sure. It's just that she's too powerful."

"Stewart seems to like being dominated. Maybe you should try it with me."

"Sure, whatever you want, if it's mine to give, you can have it."

"Awwww, that's sweet.

Just then we arrived at the house. Ann let us in quietly, but we had terrible luck, and a naked Judith was crossing the hallway as we came in. She turned and smiled at both of us.

"You two seem to have had a great day, sweetheart. Totally satisfied, I'd say."

"Hello Harry. I'm not going to make you remove your clothes in the house, but I would appreciate it if you tried. I promise not to look too closely if you get hard."

She laughed and continued on.

I already had an erection.

My first threesomeAnn and I went upstairs and undressed. I was about to pull her onto the bed, but she resisted.

"We haven't been in the summerhouse yet. No one can see us from the house and the gate you came in yesterday is usually locked. No gardener this week. Come on, I want the sun on my skin as we do it."

"Whatever you want, you know that."

"Ooh, almost forgot.

She pulled something out of her wardrobe and pulled it out.

"Remember my dog, Tramp, when we were children? This was his leash. He was a little guy, so it should fit."

She dropped in front of me, unbuckled the collar, and fastened it around my balls and my cock.

"Wow, that is really kinky. I love it."

She wagged the leash back and forth, saying "Here boy," then guided me out of the room and downstairs.

"Mum," she called, "where are you?"

"Here," she said, emerging from the kitchen with a glass of wine. "Oh my goodness."

"This is just to mark my territory. Harry is mine. You're not to touch him as long as this is in place. Understand?"

"So when it's not on, can I have him?"

"I'll tell you if he's available. I've got plans for him for a while."

She led me away towards the garden. As we walked off, Judith called out.

"By the way, Stewart is here in the summerhouse, recuperating. I've been rather rough with him today."

Ann looked back at me, excitement in her eyes.

"Well?"

"He's your present, not mine."

She licked her lips.

"I want to collect it now. Is that okay with you?"

"The last few days have been crazy with surprises, so one more won't bother me."

We went outside and she led me down the path to the summerhouse. It was already surreal, wearing a dog leash around my cock, being led naked by a stunning girl, also naked. Adding another, presumably also naked, man to the image seemed perfectly normal in the situation.

We approached the summerhouse and turned the corner. Stewart was lounging on a pile of cushions. His cock was limp and he seemed completely relaxed. He looked up as Ann approached, then smiled slightly as he guided me around the corner on the leash.

"I can see your plans," he said. "I'll go back to the house and leave you two alone."

"No, don't," said Ann. "Did Mum mention my 18th birthday present to you?"

His eyes widened, and I'm sure his cock twitched slightly.

"Yeah, she did."

"Well, I wanted to collect it today. But I want you to be here with me too. Is that okay?"

His cock definitely twitched.

"Are you sure? What about, um, Harry?"

"We've discussed it, and he's okay. I want him with us."

He chuckled. "Believe me, after three years of being with your mother, we've tried everything already."

"This is your present," he continued, "so how do you want it?"

"Like you did to Mum yesterday, but I want Harry sucking my cock as you do it. After that, we'll see what happens."

He rearranged the cushions, then led her to them, getting her to kneel with her butt in the air.

"Alright, buddy, you should probably kneel beside her head, Harry. Ann, can you reach him?"

She drew me in with her response.

"It looks fantastic. Now, am I supposed to enter you or on top of you?"

"Inside me, please. I want to feel every inch of you."

He moved behind her, feeling between her legs and adjusting himself, then slowly he pushed in.

"Wow, this feels great. Ann, I have to tell you, you're a lot tighter than your mom, but your mom has amazing control."

My hard-on twitched involuntarily at that, but Ann didn't seem to care.

"You feel completely different than Harry, a little rounder, and you don't reach as deep."

He started slowly thrusting into her. With each movement, she lurched forward onto my erection. To maintain her balance, she held on to my hips, her nails digging in. He kept going, easing his speed to give her time to adjust herself around me. She played with my cock's head with her tongue.

He started to speed up, causing her to bounce forward so hard she couldn't keep my erection in her mouth. I held her face and pushed into her, essentially face-fucking her. I timed my thrusts to match Stewart's withdrawals. She gasped for air now, both from arousal and from choking on my hard cock. I was rock-hard but still not close to climaxing. I had the feeling I could keep it up for hours.

He sped up again, really pounding her. She could no longer keep me in her mouth, so I held her head while Stewart engaged in some heavy petting. Her breathing grew ragged, and I was amazed at how much she still managed to play with both her and my cocks. She jolted backward as she climaxed, I climaxed seconds later, unloading my seed in her mouth. Stewart, however, kept pounding her. She had come quite a few times by this point, and she was really struggling to stay standing. Finally, Stewart climaxed, filling her up from before. Gasping tirelessly, he took a break, allowing us time to recover.

She woke up minutes later, finding it hard to say a coherent word.

"Fuuuck!"

She took both of our now softened cocks in her hands.

"That was amazing. I can't believe how sore I feel, but oh, it was good. Thank you, both of you."

Stewart and I exchanged glances with big grins. We kissed her on the lips, hugging her in our arms, and then when we laid her back onto the couch, she smiled at the raging boners she'd caused.

"How are we still hard?"

She reached down and grabbed me, her fingers running up and down my shaft.

"Really, you're already getting hard again?"

"Yes," she said with a playful light in her eyes. "Both of you? Well, I can't do that again - I'm fucking exhausted!"

She was still tugging on our cocks, increasing our excitement. I took a nipple and she gasped. Stewart did the same.

"Ooh, don't!" she choked out. "I'm too sensitive!"

We stopped, and she relaxed.

"What do you suggest we can do with these if I can't take you in?"

"I want to watch you two suck each other off."

We both shook our heads, unsure.

"What? You've already done that with my brother?"

"Yes."

"Would you do that for me?"

"Yes."

"Harry? Have I had all the gifts your mother said I can get?"

"You're more like your mother than just in appearance," I replied. "She has pretty kinky ideas."

"And maybe I do, too."

"God help us," Stewart said.

"Your mother came up with this idea?"

"Yep."

"Focus on your present," she grinned. "I want to watch you two together."

We looked at each other, slightly scandalized.

"What do you mean, 'together'?" we chimed, shocked.

"I mean you both give each other blowjobs while I watch."

I was shocked. "What!"

"I mean...you've both given each other blowjobs before, haven't you?"

She looked at Stewart.

"Yeah," he said after some hesitation.

"And you'd do it for me?"

"Yes."

"Please, Harry. I need to satisfy my kinkiness. And you said if it were something I wanted, I could have it."

She had a firm grip on my shaft at this point.

"You have a dirty mind, you know," I said. "I've never done anything like that and I'm not sure."

"How about you let Stewart do it to you? Please, Harry? Come on, you sound more like your mom in just these few minutes."

I looked at Stewart, who was seemingly open to the idea.

"Alright, but we should at least make sure you're okay with this," I said.

"I'm okay with it."

"Ann, you know I'll watch if you're cool with it."

"I'm fine with it. I just want to see you two together."

I looked at both of them with a mix of shock, confusion, and a certain excitement.

"What if I join in?" she asked. "I've kinda done this before."

"How about that?" I said. "We all take turns."

She nodded enthusiastically. "That'd be incredible."

We all looked at each other, not entirely sure what we'd just agreed to.

She had given me a few tugs, and I was as hard as I was likely to be after experiencing so many orgasms. Stewart was watching me closely. Ann had released him, and he, too, was fully erect. He leaned forward and, while still watching me, took me into his mouth. I discovered he had a tongue piercing, and I gasped as it rubbed against the underside of my shaft.

Ann chuckled. "Is that a yes then?"

I fell back onto the cushions and let him take me deeper. The piercing created sensations I hadn't imagined. Ann had pulled my foreskin back, revealing the glans. I shivered as he worked his way around it, then up and down the shaft, his hand replacing hers. She watched him intently as he did so. If I closed my eyes, I couldn't tell it was a man. I couldn't believe what was happening. Two days ago, I was practically a virgin, and now, following two days of mind-blowing sex, including a bondage session with Ann's mom, I had a man's tongue licking the tip of my penis.

I opened my eyes to see that Stewart had positioned himself so his cock was in front of me. We were now lying head-to-tail across the cushions. Ann watched him intently, playing with herself as she watched. I moaned, looking up at Ann's round, firm breasts bouncing gently as she played with herself. Stiff and erect between us was Stewart's penis, swaying and wobbling as he worked on me. I stretched out my arm, cupping his cheek in my hand, and pulled him towards me. With my other hand, I reached across and grabbed his cock, mirroring what he was doing to me.

She laughed happily. She bent forward and kissed the tip of Stewart's cock before sitting back and watching as I took him into my mouth. He swung around and eased himself into my mouth. I gagged initially but relaxed and allowed him in. It was a different taste than Ann's – muskier, richer – but I could still detect her, too, from when it had pushed itself deeply into her soft, sweet cunt.

I could feel his lips around the tip of my penis, the piercing rubbing against the underside of the glans. As he swallowed me whole, I swallowed him, too, deeper and deeper. I gagged at first, but then adjusted and took him farther. My nails were digging into his back as his tongue went around and I followed with my own on him. Unlike the acrobatic from our early intercourse, this was slow, calm, and restrained. Stewart pushed his cock forward, then withdrew just before I gagged. I couldn't feel the tongue piercing anymore and realized the slow, languorous movements around my erect shaft were now Ann. Then they swapped back, and I felt the two of them kissing and nipping me together. I heard her breathing heavily in what sounded like the start of an orgasm, but couldn't see how it was happening.

I felt Stewart getting harder, the taste changing to become saltier and bitter. I knew he was close to climax. I felt the same way. I didn't think I could handle it if he pumped deeply into my mouth like Judith had the previous day, but I didn't care. As I felt myself starting to stiffen in his mouth, he came, too, thrusting deeper. I heard Ann gasping also, experiencing an orgasm at the same time.

Slowly, I relaxed and he pulled out. We both returned to the cushions, limbs entangled in a mass of warm, sticky bodies. Ann was still playing with herself, reaching climax before collapsing, too.

"That was a fantastic birthday present," I panted. "What are you giving me when I'm 19?"

We stayed there for a while, resting as the night closed in. Finally, Stewart untangled himself.

"I have to leave. My flight was postponed yesterday, but I have to be at the airport at 5 a.m. I'll need sleep if I'm to be safe to fly."

He kissed Ann and then me before stepping away.

I cuddled up to her. "You are a terrible influence on me. I'm not sure I could go with another man."

"Don't deny it; you loved every minute."

"The tongue piercing was an interesting sensation, but I prefer you. With a threesome like this, you just go with the flow – it takes you where it wants you, I guess. I don't think I would just go with another man. Besides, I have a better idea of how I please you when I'm in your mouth."

"I loved watching you. You both know what works for you, so you do it to the other. It was so hot to watch. I would have loved being in you while Stewart fucked your mouth, but I was too sore. Maybe another time?"

I didn't have a chance to respond when I noticed a shadow over us. It was Judith, of course.

"I've been patient, but it's time to eat. Are you staying, Harry?"

"Yes, please, Judith."

I'm not exactly sure how well I stuck to the original text's narrative, but I gave it a shot. Let me know if you noticed any significant changes. 😊

"Don't stress, we'll keep it chill tonight. Only got twenty minutes, so make it speedy."

She vanished once more. We peeled apart understickily and stood up, noticing that the lead was still connected. I aimed to take it off, but Ann halted me.

"No, not while Mum's here."

"I could handle a gaggle of Mums like yours trying to jump me right now and still wouldn't react. You don't need to fret."

"I put down a boundary for her. If I screw up, she'll take over."

"Can't wear it with trousers on, though."

"I'll conjure up a solution. Now let's return back home and clean up."

Within the residence, we teamed up below the shower, washing off all the relics of our UEFA game in the shed. Once dried, she slapped the neckpiece back on me, then slipped the string through the anus, zipping me shut. Naturally, she couldn't resist teasing me during this process. I didn't get hard, it was too soon, but she still elicited a response.

"I'm pondering how many times we can do it in one day," she contemplated aloud.

I just shook my head.

We consumed outdoors, Ann directing me through the kitchen towards the garden.

"My," said Judith, "you're being cautious, huh?"

"I understand what you're like Mum." Pause. "On the subject, Mum, I did decide to accept my gift from you. I had fun using it."

"Hmph. Stewart didn't say a word about that when he strolled in. You going to spill any more deets?"

"No, just for Stewart, Harry, and me."

"Oh, yes. You have mysterious layers. It took me at least a month to lose my virginity and a year before I experienced my first orgy."

"Knock it off, Mum."

Judith refrained from making issues this time. At our choice, Ann and I didn't hook up privately again for a couple of days. If we had, we'd have been unable to avoid bonking and were too tender to make love comfortably.

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