grendel54321's Blog

Here’s another in the sequence of stories about Caro and my encounters with her friends.

My brother David recently re-married. At the wedding, I had noticed his attractive step-daughter July, but thought little of it until a few months later when David asked me to look after her while he and his new wife went away for a long weekend.

July arrived wearing an almost see-through white halter top, a tiny skirt, and spike heels. My daughter Helen soon had July installed in a guest bedroom.

“You know she’s a virgin, don’t you?” Helen said later when we were alone.

July was slim, with small boobs, long dark hair and green eyes, just my type. I laughed. “No. Hadn’t given her a thought.”

Helen looked dubious. “Caro told me how you initiated her sister Kristy,” she said. “We want to initiate July as well.”

I was instantly erect and my daughter laughed when she noticed.

She shook her head slowly. “You’re incorrigible. I can see you want to fuck her.”

With the excuse of settling July in, I quickly arranged for Caro and her current boy-toy James to come over, and Helen summoned her boyfriend Tom.

Late that evening, we decided on a game of truth or dare.

“Let’s make it interesting,” Caro said. “If you skip, you must remove an item of clothing. Once naked, you have to answer truthfully or do the dare.”

We all agreed and the game started tamely enough, though we were all reduced to underwear. Except Caro. She was very quickly completely naked as she deliberately passed on every round. July looked fabulous in a white bra and skimpy white panties. My cock was already getting hard in anticipation.

The questions and dares got more risque as the evening wore on and he game progressed.

“What’s the naughtiest thing you’ve done?” I asked Caro.

“I had sex with two guys,” she said. “Just once but it was fun.” She paused. “I want to do it again.”

I hadn’t known that and started to ask the obvious question. “Did they-”

Caro shushed me. “Ask me later,” she said. “It’s my turn and I like that question.”

She turned to July. “And you? What’s the naughtiest thing you’ve done?”

July blushed prettily. “Nothing really. I’ve kissed my boyfriend and I’ve felt his cock. He’s fingered me a bit.”

After that it became downright dirty.

“What is you favourite sex toy?” Caro asked.

July blushed and opened her mouth, but didn’t say anything.

“I’ve only got one dildo,” she said eventually. “I bought it online and was terrified my dad would open the package.”

“Have you every cheated on your boyfriend?” Helen asked Caro.

Caro laughed. “Yes, all the time.”

I was amused that her boyfriend James looked shocked. How little he knew Caro.

“My turn,” Caro said. “I dare you to cheat on your boyfriend.” She said, looking pointedly at Helen.

Helen hung her head briefly. “I’ve never done that,” she said. After a short paused she added “To Tom.”

Helen stood and pulled off her panties, leaving her in just a bra and revealing her shaved pussy. She glanced briefly at her boyfriend Tom, who looked outraged.

“Don’t I have a say in this?” he said.

“No,” Helen said. “The rules are the rules.”

She looked James up and down, walked over to him and held out her hand. “Come on then,” she said. “Don’t be shy.”

James looked nervously at Caro beside him.

Caro laughed. “Go on, have fun,” she said. “We’ll keep playing and you can join back in when you’re finished.”

Caro turned to Helen, grinning. “Don’t be too long, I have more questions for you both.”

Helen giggled, picked up her glass, took James by the hand, and led him towards the stairs.

Which left just four of us.

“Have you ever given a blow-job?” Tom asked July.

July blushed and shook her head. “No,” she said softly, glancing around at the obvious bulges in the blokes underpants. “I haven’t, doesn’t it taste weird?”

“Not really. You should try it, I dare you,” Caro said. She grinned. “But not Tom. At least not the first time.”

She turned July to face me. “Go on, suck him.” Caro said. “You agreed.”

July stared at my crotch where my huge erection was obvious. She licked her lips. “I’m want to, but I’m not sure I can” she said.

“It’s easy,” Caro said. “Look, I’ll show you.”

July watched wide-eyed as Caro knelt in font of me, pulled down my undies, and slowly took my huge cock in her mouth, inhaling almost my whole length. She bobbed her head for a couple of strokes, gobbling noisily.

“See, it’s easy,” Caro said. “Come on, you try.”

July came and knelt next to Caro, her eyes glued to my huge erection, glistening with Caro’s spit. When she didn’t move Caro guided her hand towards my cock.

Suddenly July pulled her hand back. “It’s too big,” she said, still with her eyes glued to it. “But I can at least try,” she continued after a long pause.

Caro took her hand again, and this time July didn’t resist as she guided it back to my cock.

July wrapped her hand around it, her fingers not making it all the way around. After a few moments, she started tentatively wanking me. She didn’t stop when Caro undid her white bra, revealing her perfect breasts, and leaving her almost naked, wearing just her lacy white panties. As July continued slowly wanking me, I reached forward and tweaked her hard nipples.

Caro sighed. “Oh for god’s sake,” she said. “Take it in your mouth.”

July wrinkled her nose and shook her head but continued wanking me gently, then she stopped, closed her eyes, and opened her mouth, Caro slowly guided her head forward onto my cock.

When her lips touched my hard cock, July jerked back and shook her head. She opened her eyes, blushing furiously now she could see my hard cock dangling in front of her face.

July muttered something inaudible, and shook her head again. She closed her eyes, leaned forward, and with the tip of her tongue, licked the drop of pre-cum off my cock.

She wrinkled her nose and spat, but she opened her mouth wide and leaned closer, until the tip of my cock was in her mouth. She slowly closed her lips around me and I felt her teeth lightly graze my cock.

“Careful, don’t bite me,” I said. Her lips were now barely touching me. “Now bob your head backwards and forwards.”

Soon, she was slowly sucking me, still with her eyes closed, taking about half my length with each stroke.

“See, I told you you’d like it,” Caro said.

July tried to speak, but all we heard was mumbling. She opened her eyes, and seeing my cock buried in her mouth, she jerked her head back off my cock and giggled. “Sorry, I almost bit you.”

She slowly wrapped her lips back around my cock, this time with her blue eyes wide open and staring up at me.

Caro knelt beside her, and watched critically. “How much can you take?” she asked. “He’s huge and I can’t quite manage the whole thing.

July came up briefly for air. She laughed. “Bet I can take it all.”

She took me in her mouth again, pushing her head slowly forward onto my cock, not stopping until her lips met my pubes and she could go no further. I felt her cough but she held herself still, looking up at me, with my cock embedded down her throat, for a few seconds, then slowly sucked me for a few slow, complete strokes.

She pulled back, spit dribbling down her chin. “I win,” she said brightly. “What’s my prize?”

Caro put her hand around my cock, and started slowly wanking me. She looked at July. “It’s your go,” she said. “Truth or dare?”

July looked at Caro’s hand wanking my cock and up at me. “You two have sex, don’t you?” She asked.

Caro and I laughed.

“All the time,” we said in chorus.

July nodded.

“My turn,” I said. I turned to Tom. “Have you ever eaten pussy?”

He hadn’t. In return he asked a tame question, easily fielded by Caro.

“I dare you to eat me,” Caro said to Tom.

Caro sat on the sofa and lay back, her legs wide with her hands behind her knees. “Come on, Tom,” Caro said. “You know you want to.”

I grinned as the bulge in his undies was obvious.

Tom knelt between her legs and started tonguing Caro’s shaved pussy.

July was clearly aroused, reaching into her panties to finger herself as she watched. Caro wasn’t impressed with Tom’s performance and started giving him instructions.

“No, not like that … yes, better.”

She continued a steady stream of commands, then sighed. “This may take a while,” she said. She turned her head towards me. “Go on, show July how it’s supposed to be done.”

“Is it okay if I do that?” I asked July, who looked nervous.

“Yes,” she said quietly, eyes still glued on Tom eating Caro.

“Don’t worry,” I reassured her, reaching out to feel her nipples then stroking her gently. I slowly took off her knickers, revealing her hairy but trimmed pussy.

“Sit beside Caro,” I said.

July dutifully obeyed. I parted her legs and knelt between them. I felt her jump when my fingers touched her pussy.

“It’s okay,” I said.

I stroked her gently, running a finger along her crack until she stopped shivering. I gently parted her lips and touched her clit with my tongue. I felt her hand on my head. I thought she was going to push me away, but it just rested there. Soon she was moaning softly.

I looked up briefly. Next to us, Caro was now kneeling in front of Tom and sucking his cock.

“Don’t stop,” July whispered, her eyes closed.

I started tonguing July again, then gently inserted a finger, very slowly, into her dripping pussy. I felt her other hand over mine, as the first knuckle disappeared inside. She was very tight. Soon I was gently fingering her as my tongue worked her clit. I added a second finger and started fingering her faster. She moaned loudly and I felt her shudder as she came.

I lifted my head from July’s pussy. Caro and Tom had progressed. She was kneeling astride him, riding him enthusiastically on the floor next to me. July was watching them intently.

“I want to do that,” July said suddenly as Caro started to moan.

“Are you sure?” I said.

July nodded. “Yes.” Her eyes never left the couple fucking on the carpet next to us.

I lay on my back on the carpet, my huge erection waving in the air. “Kneel astride me,” I said.

July tore her gaze from Caro and Tom and looked at me. She stared at my huge erection then shook her head.

“I’m sure it’s too big, it won’t fit,” she said, eyes still fixed on my cock. She looked up at me. “It won’t hurt will it?”

I shook my head. “No, I’ll be gentle.”

I held out a hand towards her. July stood up and with her eyes glued once more to my enormous hard-on, she walked forward with one foot either side of me and stopped directly over my cock. I grinned.

“Step back a little. I want you to suck me first.”

She took a step back then knelt awkwardly, apologising when her hand brushed my cock. She looked at me then wrapped a hand around my hard cock, and started to suck me, still looking at me.

“Stop,” I said after a minute or so, “it’s time. Are you ready?”

July lifted her head off my wet cock and looked nervously towards me and nodded jerkily. She looked terrified.

“Come towards me,” I said.

She shuffled forwards, jumping when my cock brushed past her pussy.

I reached up with one hand and pulled her face down to kiss her deeply. While we kissed, I rubbed my hard cock against her pussy with my other hand.

“Now sit back onto me,” I said.

July closed her eyes and slowly sat back. I guided my cock into her. She was very tight, but dripping wet and my huge cock started to slide slowly but easily into her. She stopped moving when just my tip was inside.

“How does that feel?” I asked.

She opened her eyes to look nervously at me. “I can feel you stretching me, you’re much bigger than my dildo,” she said. “It’s not fully in yet, is it?”

I shook my head. Her eyes widened and she groaned as I pushed myself deeper. I withdrew slightly and pushed again until I was balls-deep in her tight pussy. July’s eyes were still wide and she was breathing fast.

“Relax,” I said. “It’s in now.”

I let her just sit astride me for a while with my cock buried balls-deep in her pussy.

“It feels … okay,” she said, sounding surprised. She drew a deep breath and then wiggled her arse.

I started to very slowly fuck her, at first just withdrawing slightly, but gradually making longer strokes. July started to smile and soon was pushing back onto my cock with each stroke. She moaned softly as I started to speed up and rammed my cock harder into her.

I heard the door open and saw James and Helen walk in, hand-in-hand. Both were naked, James still had a huge erection, and Helen had cum on her face. From the corner of my eye, I saw Helen videoing Tom, who was now fucking Caro doggy-style. But I had other things on my mind.

I continued to pound into July who was now very loud, and her tight pussy was very wet around my cock.

“You should fuck her doggy-style,” Helen said critically, her camera now trained on us. “I know you like that.”

I looked up at July who was now moaning loudly as I rammed my enormous cock into her dripping pussy. She was about to cum again. I shook my head.

“Soon.”

Sure enough, I felt July shudder as she came again. I paused with my cock deep inside her.

“Do you want to try doggy,” I said.

July grinned. “Oh god, yes.”

She lifted herself off my cock and got into position, her arse high in the air.

I positioned myself behind her, hands around her hips, and started fucking her from behind. Slowly at first, with long deep strokes, but getting gradually faster until my balls were slapping against her each time I pulled her hard back onto my cock. She quickly reached climax again, which drove me over the edge and I came deep inside her.

I continued to fuck her slowly for a few long lazy strokes, my cum oozing out of her pussy around my cock. When I pulled out, July turned, still on her knees, and blushed furiously when she saw my cum-covered cock, still hard in front of her.

“I guess I’m not a virgin anymore,” she said.

I grinned. “Definitely not. I dare you to suck it clean,” I said.

July grinned and took my cock into her mouth briefly. She swallowed.

Let’s go for a shower,” I said to July. I pulled her to her feet and we went to clean up. As we left, I grinned when I saw my daughter Helen had switched her camera back to Caro, who had fulfilled her wish for sex with two guys again: she had Tom’s dick in her arse and was sucking James.

That night July slept with me and we fucked sporadically. The rest of the weekend, July was voracious, and she demanded all the blokes fuck her in turn.

Finally the weekend was over and David collected July.

“Did you miss me?” David asked.

July shook her head. “To tell the truth, no, not for an instant. I hope you had as much fun I did.”