An Unexpected adventure with Robin and Olivia

Chapter Eight: The Next Question

Life went back to normal with work and home. I had more time to visit Robin and Olivia. Babysitting duties had ended when Olivia turned eighteen. Olivia proved she could be trusted and so she stayed home by herself or told her mom when she went out with friends. And Robin said Olivia always was home by a reasonable hour. We had not had time or the opportunity for another payment. But, the next step started to form.

Olivia opened the door when I arrived. She was working on dinner since Robin was due home around 6:00 pm. Summer was almost over and then she’d be back in school, that is college. “How’s my favorite niece?”

Olivia replied, “Good, except I am having trouble with the bread.”

“What’s wrong?”

“It is not rising properly. I thought I mixed it correctly.”

“Did you put yeast in it?”

“Yes. I put everything in it but it just seems to be blah.”

“Was the yeast old?”

“I don’t know.”

“Well, I am sure it will taste fine. They will just be flats.”

“Hey, don’t make fun of my cooking.”

“No fun, just happy you can cook.”

“Since your mom is not here, when did you want to make another payment?”

“I have been thinking about it. I also said something to Julie about her experience with boys.”

My heart skipped. “You did not say anything about the payment?”

“No. Absolutely not. I was just curious about her knowledge.”

“Why?”

“I really wanted to make the payment as good as possible. I have not stopped thinking about it. My pussy stays wet. But, we have to wait for mom to work late. She has not been cooperative lately.”

“Okay. Let me know.”

Olivia was quiet for a while. I looked at her and she was obviously arguing with herself. So, I interjected, “What are you trying to decide?”

She glanced at me with a puzzled look. “How did you know?”

“Your face gave you away. What were you thinking?”

“After talking with Julie, I found out she hasn’t actually seen a guy’s penis. She has watched porn and knows what happens but that was not the same. She said the boys try to get into her pants but they are all the same. They want to use girls and then go to the next girl. And, she did not want the wrong reputation so she always says no.”

“I can understand that.”

“So, I was thinking if I could invite Julie to our payment time.”

“What do you mean? Will she participate? Watch? What?”

“I was thinking she could also masturbate for you. And you could let her see your cock up close.”

“Are you serious? How are you going to convince her?”

“I am still working on that. I may just ask her if she’d like to see a real cock and that she would have to masturbate for the guy.”

“Do you really think she’d go for it?”

“I don’t know. Maybe.”

“When are you going to bring it up?”

“Soon, I wanted to make sure you would be okay with it.”

“What is not to like. Two girls masturbating for me. And then a hand job in return.”

“So, you are okay with it?”

“Yes.”

We had just finished discussing the plan when Robin pulled into the garage. We had a nice dinner even if the bread was flat. Then Olivia went to her room, leaving Robin and I to talk.

“Robin, it seems that you are doing well with Olivia, now that she is getting older.”

“Yeah, she is a good kid. I am thankful for the way she turned out, even with the situation with her dad. It has been nice having you near. Olivia has really been saying nice things about you.”

“That is nice. I think she is a nice young lady. I always look forward to spending time with her. I don’t know why she wants to spend time with me.”

“I am glad ya’ll are getting along well. I need to ask a big favor.”

“What do you need?”

“You know that project I have been working on for the last eight months.” “Yeah,” I replied. She continued, “I need to be gone for two weeks. And, it will occur with the start of college so I need you to ensure Olivia gets settled into her classes.”

“That should be fine. My work is now routine so there should be no issue. And, I can adapt my schedule as needed. Working from home is more flexible than an office.”

“And, I would like you to stay here with Olivia during that time.”

I was thinking how perfect this was going to be. It set up the perfect time to get the second payment from Olivia and with Robin gone she could plan a sleep over with Julie. That was more than I could ask for. “Robin, I think that will work fine. I hope your trip goes well.”

“Mark, I am so thankful to have you near.” No, I thought, it is me that is thankful. But I said, “I am always happy to help.”

She seemed relieved. Now I knew what to plan. Before leaving I went to say good bye to Olivia. I knocked on her door. She answered, “come in.”

“Hey, kiddo. Your mom asked me to stay over while she is out of town for two weeks. I think you could have a sleep over with Julie during that time.”

“That would be perfect. Now I know what to do to convince her.”

I left and headed back to the apartment. I was horny. Two girls to watch masturbate. This reminded me of South Korea. But there I would also fuck both. As much as I would love to fuck Olivia that was not going to happen. When I got home I put in one of my SK videos and enjoyed reminiscing about some of the girls I fucked. And, I shot my load thinking about two young pussies.

Chapter Nine: The Sleep Over

Olivia went over to Julie’s house the week before the planned sleep over. She was so excited. “Julie, how would you like to have a sleep over next weekend. My mom is going to be out of town and my uncle will be the chaperone.”

Julie was not very enthusiastic. “Why don’t we wait until your mom is back. Your uncle is nice but he just does not seem to be that much fun.”

“Oh, he is a lot of fun. And, I wanted to have the sleep over when mom was out of town.”

“So, what am I missing?”

“Well, I don’t really know how to explain it.”

“Then just say it.”

“Okay. I did something that would get me in a lot of trouble with mom. Uncle Mark and I worked out a fair payment or punishment so that mom would not know. My next payment is due next weekend. And, I know you would like to participate.”

“Hold on. You want me to participate in your punishment?”

“Well, yes and no.”

Julie was puzzled. “So, which is it?”

Olivia decided to change tactics. “I know you have only seen a penis looking at porn.”

“What does that have to do with the sleep over or your punishment?”

“Would you like to see a guy’s dick for real, especially one that is erect.”

“Of course. I have always been curious. But, I am still confused.”

Olivia blurted it out. “I filmed my uncle masturbating without his knowledge and he found out. I had to masturbate while he watched. Then he was horny and he let me see his cock up close and I gave him a hand job. It was fantastic.”

The look on Julie’s face changed from shock to disbelief to excitement to puzzled. “What? You watched your uncle and filmed it, then he found out. And now you have masturbated in front of him and gave him a hand job. Really?”

“Yes.”

“That is a lot to take in. So, what is the punishment?”

“I filmed him three times so I have to masturbate for him three times. One is done. Two more times left. It was so hot. I came more than ever before.”

“So, what about the sleep over?”

“You are invited with one condition.”

“What condition?”

“You have to masturbate in front of him. And then you will be able to see and touch him. You could give him a hand job.”

“Are you serious?”

“Yes.”

“When do you want to know?”

“Before the weekend. And you can’t tell anyone.”

The next four days went by slowly. Olivia did not bring the subject up but acted like nothing had happened. She was excited but needed to keep her mind off of it. When she did think about it she felt tingly and her pussy became very wet. She changed panties twice a day to keep from having wet spots on her pants. Finally, Julie pulled her aside. “Okay. I will join you.”

“Are you sure?”

“Yes.”

So, the plan was set in motion. Now, I called Mark.

“Uncle Mark, Julie agreed to the sleep over.”

“How did you convince her?”

“I told her the truth.”

“What? How much?”

“It is fine. I told her what I did and the punishment. She wants to see a guy’s cock for real. So, she is in.”

“Okay. We will need to finish the planning.”

The next couple of days were busy with school since Olivia was back to regular attendance. Summer was over. Everything was going fine until the sleep over leaked out. Now Vickie and Jenny were coming to the sleep over. That was not expected and Olivia could not say no. We will have to postpone the payment.

Friday afternoon came and the girls all arrived. They were having snacks and talking about the fun for the night. I was cooling myself. Just thinking about the planned fun made my cock press against my pants. It is a good thing I wore jeans. But, the tightness hid my erection while making it uncomfortable. Now I will have to suffer until I can go take care of it after going to bed. Not exactly what I planned. I was in the kitchen but could hear the girls talking. They just ignored me.

The girls started playing truth or dare. They used a bottle and spun it. It appeared they had played this game before. They spun the bottle and it landed on one of the girls. Olivia asked, “what would you like to do with a boy Truth or dare.” One of them, I think was Jenny, said she wanted to see his dick. They all giggled. Then they spun the bottle again and it landed on Olivia. I was interested in her answer. Julie asked the question, “Have you ever touched a real dick?” Now this answer would be interesting. Or, would she choose the dare.

Olivia hesitated. She was thinking. What was she going to do? Then she said, “Truth, yes.”

That raised a ruckus. None of them believed her; except one knew the truth. They spun the bottle again. It landed on Julie. This time Vickie asked the question. “Have you ever showed your privates to a boy?” Julie answered quickly, “No.” So, she was going to masturbate in front of me and that was going to be her first time showing her pussy to a boy. Now that was interesting. And my dick got harder.

They kept playing and got silly. I don’t know why they stopped the more interesting questions. Maybe they realized I was able to hear.

They changed into their pajamas. They settled down for a bit and then in a loud voice I heard, we are ready. All of them said it together. I was watching tv and did not move. Then I heard them shout, “We Are Ready!”

That got my attention. I got up and went to see what they were doing. When I walked in the sight I saw shocked me. I was speechless. I could not even think. Then, Olivia said, “sit over there” and pointed to a chair set up for me. I sat as directed. All four girls were naked from the waist down. And they all lay with their knees up showing me their pussies. Four 18-year-old pussies. I had already seen Olivia’s pussy and it was still shaved smooth. And it was beautiful. Julie was neatly trimmed and her tan lines were obvious. She had meaty lips that were so tempting. I could spend hours nibbling on her pussy. Vickie had the largest breasts of all the girls. She wasn’t overly big but definitely nice. Too bad they were still covered up. Her pussy was nice. She was shaved but had a little landing pad. Her pussy was tightly closed but when she spread her legs her vagina opened up like it was winking. So nice. My dick was not going to stay in my pants long. And then there was Jenny. As much as I thought Olivia had a beautiful pussy, Jenny was gorgeous. Her red pubic hair was fine, barely hiding her pussy. The flame red pussy was so nice. I wanted to go down on her.

I sat in the chair and all four girls started rubbing their pussy. I watched them. I moved the chair closer to get a really good view. The moaning led to more moaning. I watched Julie, Jenny, and Vickie. Vickie slid her middle finger inside her pussy. She was very wet. I could hear the juices. Jenny was starting to shake. She was nearing her orgasm. I watched. I could smell the musk of their pussies. I was so horny. I could fuck all of them. Jenny started to whimper. She was so sexy. “Oh, oh, fuck. I’m cumming.” She lost all control and cried out in pleasure. She was still settling down when Julie came. Olivia was next and she was shaking as a second orgasm was building. I think she was turned on by the other girls cumming. Then Vickie started cumming. Then Olivia came again. Wow. That was amazing.

The girls laid there for a while and then Olivia said they would call me a little later. I was so hard. I hoped to have relief. The girls recovered and got some snacks and drinks. Then they called me again. I went in and Olivia escorted me to the chair again and told me to stand up. I did what I was told. Then Olivia told Jenny to remove my belt. She came over and looked at me. I slightly nodded my head giving her permission. She unbuckled my belt and pulled it out of the loops. Then Olivia told Vickie to unzip my pants and pull them down. Vickie came over and undid the button, unzipped the pants. She let her hand linger touching my hard cock. Then she reached up and slid my pants over my hips and down to the floor. I stepped out of each leg. Vickie tossed the pants on the floor. I was wearing boxer briefs that allowed my hard cock to push out. The girls were purring seeing my cock outlined in my underwear. Olivia told Julie, “You get the best part. Pull his underwear down slowly. Take your time.” Julie put a hand on each side while she was on her knees looking right at my cock outlined in my briefs. The other girls were getting closer to seeing it for the first time. Julie slowly slid the briefs down until they could see my pubic hair that I had trimmed. Then she pulled them down revealing my shaft. And finally, she pulled then down enough to release by cock. It popped out and hit Julie on the chin. The girls laughed. But their eyes stared at my hard cock.

“Okay. Sit in the chair.” I did as Olivia requested. Then she said, “Everyone gets to stroke his cock. You can look closely. Make sure you look at his pre-cum, it will leak out as a lubricant.” The girls were still reluctant to touch me. Then Olivia broke the ice. She started stroking my cock. It felt so good. I knew I would have to use my best skills to hold out for a long time so they all could stroke me. Olivia said, “You want to pay attention to keep him from cumming too soon. We all want to enjoy this. “That feels so good.” I was enjoying the attention.

Olivia told Jenny to touch me. She reached over and when she brushed my dick it jumped. She jumped. And the girls laughed. I told her it was okay. So, Jenny wrapped her hand around my shaft and started going up and down. She was grabbing a bit too hard. “Jenny, take it easy. Loosen your grip a bit. Let your hand loosely hold my cock.” She did what I said. “Like that.” She was doing a good job. Then Olivia told Vickie to take over. She was observant and followed the direction. They had been stroking me for about 15 minutes. I was really enjoying this. Olivia told Julie it was her turn. Julie was a natural. She was working my cock with both hands and started rolling her hand over my cock head. I moaned. And she kept going.

Then Jenny asked what my cock tasted like. Olivia said she did not know. Before I knew what was happening Jenny wrapped her lips over my cock while Julie stroked me. That was unexpected and I just about came. I backed off my urges and let her suck my cock while Julie continued her rhythm. Then Vickie replaced Julie. Jenny stopped sucking me. Vickie was doing a good job. I was getting closer. Then Olivia moved closer and I was thinking she wanted to see me cum close up. But, I was wrong. She wrapped her lips over my cock. I was shocked, but it felt so damn nice. Watching her suck my cock was just the best. I told her I was going to cum so she stopped and all the girls got close. Both Jenny and Julie started stroking me together. Two young girls wrapping their hands around my cock was just too much. I spurted at least 18 inches high hitting Vickie and then squirted four more ropes. The girls were all excited to see it. Jenny wiped a little on her finger and tasted it. She said it was a little salty but not bad. The other girls copied her.

That was so sexy. Julie said she was still horny. All of the girls were horny. They started masturbating again rubbing their clits. I started stroking my cock and it again grew. I was hard again in no time. We were all masturbating watching each other. Then Julie stood up and sat down on my cock with her pussy all the way down on my cock. Her pussy felt wonderful. She lifted up and then slid down. She got into a regular rhythm fucking me. I was happily surprised. Olivia and the other girls stopped their own masturbation to watch Julie fucking my dick. Their eyes were glued to my shaft being covered in Julie’s juices as she fucked. They were spellbound. Then Jenny told Julie, “My turn.”

Julie lifts off and plays with her clit. Jenny lines my dick up with her pussy. She pushes down but stopped. I could feel pressure. Then I feel her lift up a bit and forcefully push down. It went in a little and Jenny cried out in pain. I was concerned and started to ask her if she was okay. But she beat me to it. She lifted up a little and started pushing more until I was completely in her. She felt really wet. My cock was not going to last with such a warm slick pussy. And, I have always had the hots for red headed girls. She made my night. It did not take long and she started shaking until she moaned loudly. Her orgasm lasted about a minute. She squeezed my dick with her pussy.

Jenny got off and I saw the blood. I realized, she was a virgin. She had fucked me. I was the first dick in her pussy. Wow. Then, Olivia got a wash cloth and cleaned me up. Vickie was next; she sucked me and then placed her pussy on my cock. She had no issue taking my cock in her vagina. She got into a regular rhythm and it felt great. Having cum once gave me more staying power. I was getting into it when she stood up and motioned to Olivia. Olivia looked at me and I nodded. She came over and rubbed her pussy on my cock. Then she sat on my dick. All the way and just sat there. Then she leaned in close and kissed me. She said, “This is the best punishment ever.” I had to laugh. Then Olivia went to town fucking me. She was fucking hard and I was getting close. I told her “I am going to cum.” She said, “Go ahead.” Now my head is spinning. What did she mean? Is she on the pill? She kept on fucking. “Olivia, I am going to cum. Not pregnant.” She said, “Cum in me.” But we had not planned that. I was so ready to cum in her pussy. Then my nuts tightened and my dick started to swell. I spewed sperm in her pussy. It was so hot. I hugged her and kept her pushed down on my dick. We clung together. Julie, Jenny, and Vickie all came with me.

Once the euphoria wore off my panic increased. I had just seeded my niece’s pussy. What if she gets pregnant? Thankfully, Olivia told me that she was on the pill. She had done that to avoid getting pregnant. The girls cleaned up and went to sleep. I cleaned up and contemplated the events of the night. I had fucked all four girls.

The next morning, they all went home. Olivia sat down and told me what I did not know.

“Did you enjoy last night?” Olivia asked.

“Of course. It was fantastic. But, how about you?”

“I really liked watching my friends and you having sex.”

“You have to explain it to me. How did it happen? And, did you know Jenny was a virgin?”

“Yes. I knew it. Also, the rest of us were virgins, too.” Olivia explained.

“What? I did not know.”

“You were not supposed to know.”

“Only Jenny had her hymen.”

“Jenny is not into sports. Julie, Vickie, and I play sports and lost our hymen a while ago. But, we had not had sex until last night.”

“How did you set it up? You only told me about Julie.”

“It was Julie who did it. They were all at her house after I initially asked her and she was debating about the proposition. She posed the question to them. She told me she asked them what they would do if they were given an opportunity to see a guy’s dick up close if they would masturbate for him. And, there would be no obligation or other requirement afterwards.” I was listening intently. I did not know how girls really thought. Olivia continued, “So, they asked about the possibility of fucking the guy. Julie told them they could if they chose to.”

“So, she said that.”

“Yes. I think she figured a boy would not turn down the chance to fuck a girl.”

“She was probably right.”

“Julie then asked them if they’d like to join us in masturbating and getting to see a hard cock up close. They agreed.”

“Why did you not tell me?”

“I did not know. While you were away she quickly told me and then we planned to use the truth or dare game to get you hooked. We already knew the answers.”

“You, Olivia, are sneaky.”

“I am glad it worked out. I was worried you would back out.”

“I was shocked you fucked me. I expected you to avoid it since we are related.”

“I wanted to fuck you the first time I saw your cock. I just did not have a way to ask.”

“I understand.” I did understand. I had wanted to fuck Olivia too but there was no way to do it without her equal desire. I guess we both got what we wanted.

Olivia then added a new bit of information. “The girls asked if we could do it again soon. They all enjoyed it.”

“Well, we will need to wait until your mom is away on a trip.”

Olivia said, “That would work. The girls will be waiting for the invite. And this time we can get to the fun sooner.”

“Olivia, make sure they are all on the pill. We don’t want a mishap to occur.”

“Julie was already on the pill. Her mom wanted to avoid some problems if Julie did have sex. And, we told Jenny and Vickie to get an appointment with their doctor. They need to be on the pill. None of us want to get pregnant.”

“Were they at the right time last night?”

I was not too worried but did want to avoid a problem. “All of us were at the month where it was unlikely.”

“Your mother will be home in a few days. This has to be kept quiet. Otherwise, there will be major problems.”

“No one will say anything.”

“I really hope so.”

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An Unexpected adventure with Robin and Olivia - Chapters 8-9