Hot Summer Night Ch. 18

Julia smiled and said, "OK. Get up on the bed on your back and we will go in order." Olivia did as instructed. Julia climbed up between her legs with the small dildo and made like she was the guy about to fuck her. She put the dildo up to her pussy like it was a guy's cock and moved her knees between Olivia's spread legs. Julia pulled her knees up and Olivia could see that made it easier to spread her legs. Julia moved the dildo to the entrance of Olivia's pussy and pushed it into her.

Olivia's face contorted. She was in a lot of pain. Julia said, "You are a virgin I assume." Olivia nodded. Julia continued, "OK. I am not going to push into you because you are going to feel that pain until your hymen is broken. There may be some blood and probably a lot of discomfort the first time which our plan says will happen this afternoon unless to choose to break it yourself with this big dildo. It's up to you." OK?"

Julia continued, "OK. This is the so-called missionary position. Many men only use this position because it puts them in command. Now. I am going to lie on my back with the cock in the air and you are going to straddle my hips and sit down on it and push it into your pussy. She did as instructed and moved her wet pussy down on the dildo. She cringed when the small dildo enter her.

"OK. The next position is you on your hands and knees and the cock is pushed in from behind you." They did this and Olivia cringed again when the dildo entered her pussy. Julia said, "Now if you want to take the initiative you can push back against his cock or you can stay still while he flexes his hips into you.

Olivia said, "Ok. I think I have it. I wasn't even sure where the cock was supposed to go. Front or back."

Julia laughed and said, "Well. I might confuse you but a cock goes up your ass very nicely and the feeling is amazing. But, let's not go there today. OK?" Julia got up off the floor and said, "Now for the rest of the time until game time you need to practice with your mouth giving blowjob and especially putting this large dildo in your pussy. It will hurt badly but you will find the location of your hymen. Once that is broken you are no longer a virgin you will be a woman. It's called 'losing your cherry'. Go back to your room and practice. OK?"

Olivia stood up and pulled her clothes on while Julia put both Dildos in a bag and handed it to her. Olivia teared-up as she hugged Julia and then Carrie and went out the door bag in hand. When the door was closed Julia looked at Carrie and they launched themselves at each other and fell on the floor where they were standing. Instantly they were in a '69' position with their tongues working the other's pussy.

Neither lasted very long before they were both having massive orgasms. Carrie was about to crush Julia's head between her thigh as she vibrated and then pulsed. Both pussies were throbbing on the other's tongue.

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It was nearly 11:30 before Carrie and Julia walked up to my chair in smoking hot bikinis, promptly stripped them off and stood before me. I was still asleep. Carrie bent over at the waist displaying her pussy from behind and sucked my flaccid cock into her mouth.

I came awaken in the best possible way. Carrie was blowing the top third of my cock and Julia was kissing and licking the other two thirds. My cock was instantly hard as a steel pipe. I figured my girls were just messing with me but they didn't stop their action except to switch shares of my cock between them and keep right on going until I groaned and my muscles all tensed and I blasted cum from my cock into Julia's mouth. She took two shots and pushed it to her mother to finish catching the rest. Five more shots filled her mouth and some drooled down her chin. The both swallowed and Julia moved into lick the cum on Carrie's chin. They promptly sat down in their chairs.

Carrie said, "Pleasant dreams I hope." I just smiled.

Julia proceeded to tell me the whole story of their morning with Olivia. My cock jumped and Julia said, "Well that seems to turn you on doesn't it?" I nodded and my cock jumped again as if to confirm.

I said, "OK. The plan is on for let's say 3:30 this afternoon."

Carrie said, "It should be hard to pull off. Olivia told us the other girls in her group are begging her to introduce you to them. So the introductions will be made and we will go from there."

We lounged in our chairs drinking our drinks until 1:00. We got dressed in our skimpy suits and walked over to the burger bar and had lunch and a few more drinks. As we got up to head back to the pool I noticed Olivia's gang come strolling in with shopping bags in hand heading for their suite. Carrie said, "Well Olivia is either ready or she's not. By the way, we confirmed she was on the pill and she is eighteen." We headed back to the pool.

When we got back we had to wade through bodies in various sexual positions to get to our chairs. The pool was lined with guys getting blowjobs from any woman that walked by. Everyone was in heat it seemed. Perfect.

I went to the bar but Phoenix was off today so I order drinks and carried the tray back to our chairs. We were getting a little buzzed.

Around 2:30 Olivia and her gang showed up. As usual they sat right behind us. There were plenty of vacant chairs. Everyone was on the grass, deck or pool. I followed them all the way in until they walked past me. I said, "Hello Olivia. You look fantastic today." She did too. She was wearing a thong bikini bottom with the ties pulled up high on her hips. Her ample tits were hugged in a strapless triangle top just barely covering her nipples. The others were dress similarly but I didn't say anything to them.

Carrie spoke up and said, "Olivia. Come over here and model that suit for us." She was adlibbing and she caught Olivia by surprise. She walked meekly over to stand in front of us. Julia whispered, "Confidence. Confidence."

Olivia straightened right up; thrust her ass out behind her and her tits in front. She pushed her fingers through her short hair and put on a pouty face. She moved her hands down over her tits along her sleek waist and over her hips. She turned around slowly in model posses so we could see it all. 'Holy shit. I was thinking. What an incredible transformation.'

Carrie, Julia and I started clapping and hooting. Other's who had been watching Olivia did the same. She turned beet red but she continued to show her confidence by bowing to everyone around. She walked back toward her friends with the model cross-over step with hips swaying. My cock jumped up and stayed up. Olivia was smoking hot.

Behind us, her friends were all hooting and hollering about Olivia's show. I was happy for her. I knew she had to be pleased with herself. I reached over and high-fived Carrie and then Julia. They were both grinning like Cheshire cats.

Olivia came back around behind us and stooped down so she could speak softly. She said, "Thank you. Thank you. Thank you." She hugged Carrie and hugged and kissed Julia. She continued. "I feel so good right now. I've never felt like this before." She was bubbling. She whispered to Julia, "3:30 right?"

Julia nodded and whispered back, "Break a leg."

At 3:15 Carrie and Julia got up and Carrie said, "We're going to the bar." As they walked away I couldn't help but watch every movement of her fantastic body. Her hip sway would raise a corpse's cock. The bounce of her breasts? Erotic. My cock that had been resting peacefully on my left thigh jumped up as if to watch too.

I said out loud to no one particular, "What a body."

A guy sitting nearby was watching her too. He said, "And she gorgeous too. She is the most beautiful woman I have ever seen in person. You see women like that on TV or in the movies but you always wonder where they come from because you never see one personally." Still staring at Carrie he said, "Is that your wife?"

I quickly responded, "I wish. I met her and her companion a few days ago."

He said, "You tapping that?"

"Both of them actually. They're both unbelievable in the sack." I said. The guy was jerking on his hard cock as he watched Carrie and Julia sit down at the bar. I looked over at him for a moment. He was about forty and was in pretty good shape. He was starting to bald. I guessed he was 5'10" or so and probably weighed 175 lbs. I looked back at Carrie and Julia. They had leaned in to kiss each other.

The guy groaned as he continued jerking off. His dick was uncircumcised and was average size, around 6" long. I leaned toward him and softly said, "You know, I'd bet anything that she would like the looks of you. Why don't you take a run on her? My guess is that you could get them both."

He broke his stare and looked over at me. "Seriously.", he said. I just nodded and lay my head back against the chair and closed my eyes. I heard his chair scrape on the deck and he pulled himself to his feet. I opened my eyes and watched him head for the bar. I closed my eyes again.

I could hear Olivia and her five friends chattering behind me. One of the friends was saying, "Come on Olivia. We have to meet this guy. He's alone. Now is a good time." I smiled and thought, "I love it when a plan comes together."

Olivia said, "Come on guys. He is a nice man. I don't want to impose."

The other friends continued to harass Olivia and at 3:30 she relented and said, "Ok, I will introduce you. After that you are on your own. OK?" A chorus of 'OK's' followed.

Seconds later I felt someone sit on the edge of my chair. A hand touched my arm. I opened my eyes to see Olivia sitting there beside me. She still had her amazing bathing suit on. I could see her 'friends' standing behind her. They all had their suits on too. All of them looked scrumptious as most any eighteen year old looks to a forty-three year old man. Olivia said, "Mark. I would like to introduce you to my friends." She pointed at who I figured was the leader of this click and continued, "This is Gwen." and she continued pointing to each one, "This is Sophi, Angie, Adel and Stevie."

Stevie piped in, "You know like Stevie Nicks?" and started giggling. I looked at her and thought, 'seriously.'

Olivia looked back at me and said, "This is Mark." A chorus of "nice to meet you' followed.

I pulled my chair back up and sat up straight. My cock lay completely flaccid on my left thigh. I said, "Please. Pull up a chair and join me. Can I get you something to drink?"

Gwen said, "No thank you we have drinks." She was slurring her words a little. Stevie and Sophi scurried back to their table and brought five drinks and placed them on the table beside me. They pulled up chairs around me as close as they could get and sat down. I asked them a bunch of question about where they lived, etc. They were all eighteen and had graduated from high school this past June. Some were going to college in a week or two. Others had no idea what they were going to do. All had boyfriends or at least they said they did.

After some silence, Gwen leaned forward and put her hand on my leg and said, "We were planning to bring our boyfriends but when our parents found out that was squashed." She continued on and totally surprised me, but it fit in the plan, "We came here to have sex. We are all experienced with sex. Well, except for Olivia. We begged Olivia to introduce us to you because, well ummmm, we want to have sex with you - well not Olivia, I guess. She doesn't know anything about it and you probably wouldn't want someone who isn't experienced; you being older and all." She pulled her hand off my leg and sat back in her chair.

I looked at Olivia and she played her role by looking all shy and staring at her feet. I said to Gwen, "Well, you are all very attractive and I'd be honored and if Olivia wants to she is more than welcome. I'm sure you all would be glad to teach her since you already know everything there is to know."

Gwen and the others broke out in smiles as they all pushed their chairs closer. I glanced over at Carrie and Julia at the bar and just shook my head when I saw the guy I had been talking with earlier sitting on the edge of the bar with Carrie's head buried in his crotch. Her head was bobbing up and down with Julia's head in Carrie's lap sucking on his balls. My cock surged at the sight.

Gwen was the first to start. She knelt beside my chair and wrapped her right hand around my cock. It was almost at max dimension from the view at the bar. I said, "How about you ladies make yourselves comfortable." Olivia stood first and made a big show of taking off her bathing suit and stood there naked with her hands on her hips before sitting down in a chair beside me. The others took the hint and stripped out of there suits as well. Gwen had a gorgeous body with large breasts, trim waist, flat stomach and nice rounded hips. She had already blossomed from a girl's body into a woman's. Some of them had not but they were still most attractive.

Gwen reached up and took my cock and stroked it for quite a while. She never made a move to put it in her mouth or spit on it or anything. If she considered herself experienced I shuddered to think what the others were like. Finally I looked at Gwen and said, "Gwen, honey. You're starting to chafe my cock. Can you put my cock in your mouth and give me a blowjob?"

Olivia smiled but the others had a horrified look on their faces because they knew they were next. Gwen looked at the group and back at me and then down at my cock which was starting to get soft. Gwen leaned over and put the tip of my cock on her lips and kissed it several times. I reached down and put my hand on the back of her head and pushed her down slightly, forcing my cock between her lips. I stopped pushing when her lips were over my cock-head. She flicked her tongue on the head and pulled back off. I pushed her down a little further. She gagged almost immediately and saliva spewed from her mouth onto my cock as she quickly pulled her head off.

I said, "Ok. Gwen you obviously don't like sucking cock. That's fine. You wanted to have sex with me and I want to have sex with you. I guess that means that you want to fuck. Do you want my cock in your pussy or your ass?"

She hesitated and said, "In my pussy?"

"Is that a question or an answer?" She didn't answer. "Ok. Pussy it is. I seem to have adequate lubrication from your spit. "What position do you like the most?" The others were looking at each other like they didn't understand the question.

Olivia spoke up for the group, "You know. Do you like the missionary position, being on top facing front or back, or doggy?" Gwen and the others stared at Olivia. Olivia said, "What?"

Finally Gwen said, "How about doggy?"

I said, "My favorite. Take the position sweetie." Gwen had seen dogs fucking so she got on the deck on her hands and knees. I stood up with my flagging pole and said, "I need some help getting this thing back up." I pushed my crotch into Angie's face and she touched it with her tongue. I said, "Can you put it in your mouth?" She did but very carefully. I began stoking in and out of her mouth with just the head of my cock. Tears started rolling down her cheeks. I pulled out and offered it to Sophie. She declined with a shake of the head.

I looked at Stevie and then Adel. Stevie looked like she would give it a go. She got on her knees and pushed her mouth over the head and about a third of the way down my cock. She gagged a little, marked the spot with her hand and started furiously blowing me. Finally, one of this bunch had some experience. She was doing fine until my cock grew back to maximum size and then her teeth came into play. I looked down and said, "No teeth." and wagged my finger.

Stevie pulled off and flexed her jaw, "You're too big for me. My boyfriend has a small dick and I can handle him fine."

I said, "No problem Stevie. Nice try. How about you Adel?" She was game and was doing a decent job with her mouth, tongue and hands synchronized. She had done this before. I pulled my cock from her mouth and said, "How about you Olivia?"

Olivia moved out of her chair and knelt on the deck in front of me. She looked up at me and took my stiff cock in her hands and started jerking me off with that counter-twisting motion that Julia had taught her. I groaned. At that she pushed the head into her mouth and wasted no time on the head. She pushed her mouth down my shaft until nearly three quarters was in. She gagged slightly and marked the spot with her hands. My head rocked back on my shoulders. 'How in hell has she got that much cock in her mouth?' I thought.

She pulled back and pushed her mouth back down. She held her hand on the quarter left over and ran her thumb up and down the underside. She looked into my eyes the entire time. She continued the motion for several minutes. The others were slack jawed watching Olivia administer an amazing erotic blowjob. She had a smile on her face the whole time. It was obvious she was into it.

I was going to blow my load any second so I slowed Olivia down and reluctantly pulled my cock from her face. She held the suction until a loud 'pop' as she pulled off the head. She grinned all over. I just looked at her for several moments. My cock was hard as a steel pipe. I turned back to Gwen who was still on her hands but had put her ass down on the deck. I said, "Ok Gwen? Are you ready?"

She pushed herself up on her knees again. I bent down and licked her pussy and asshole and she jumped a foot. "Sorry Gwen. I just wanted to make sure you are ready. You're dry as a bone. You have no lubrication yet. I will hurt you like this. Are you sure you want to do this?" She just nodded.

I turned back to Olivia and asked her to spit on my cock a few times and get me lubricated. Olivia said to everyone's shock, including mine, "I'm lubricated and I'm very horny." She sat back and spread her legs. She was sopping wet. She ran her fingers around in her pussy for a moment and then pushed her fingers into her mouth and sucked on them." 'Julia had created a monster. A very erotic one.' I thought.

Olivia said, "I want to be on top. OK." I thought, 'a wise choice then she can control the action.' I lay down on the deck. My cock flopped onto my stomach and lifted back up. Olivia crawled over and placed a leg on each side of my hips and sat up straight like she was in a saddle. I looked down at her as she reached between her legs and positioned my cock at the entrance to her pussy. She slowly pushed the head in. Once inside, her fingers went to her clitoris and gently began stroking it. She sank slowly down my shaft. I was sure she was a virgin so I would be hitting her hymen soon.

While looking down into my eyes she sank lower and lower. My eyes went wide and she grinned at me as a very serene look came across her face. She sank lower and lower until my entire cock was buried in her pussy. Suddenly, her head snapped back and her mouth opened to form an 'O'. Every muscle in her body tensed. She increased the pace on her clit. Her chest surged forward and her hips rocked back and forth dragging my cock in and out several times with the flex of her hips. 'Jesus Christ. She is having a huge orgasm.' I thought. After several minutes she settled down and started fucking me. I thought, 'Fuck, she is tight.' More spasms hit her and when her pussy clamped around my cock I thought she would crush me.

When she looked back down she was looking to our left. I turned to see Carrie and Julia standing a few feet away with huge smiles on their faces. Julia was quietly clapping and mouthing the words, 'You Go Girl.'

After several minutes I was about to blow my cum in her. I had to hold off if I wanted to finish this sting. I looked up at Olivia and said, "Olivia. Honey. I still have to do your friends. I'm not going to last another minute if you keep this up."