Summer Break with Jane and Tony Ch. 01

Debbie interjected, "You aren't hurting her, really. It's an erotic outlet that accentuates the passion. Think of it like pinching Jane's nipples. You know how much she likes her nipples pulled and pinched really hard. It's the same sort of thing. It's pain but it's good pain."

Jane said, "Yeah! That's exactly right. You know how hard I like my nipples pinched. If you just walked up to me and surprised me by pinching my nipples hard it would hurt like hell. But when it's done in the throes of passion it feels marvelous! Will you do this for me?"

Their argument made sense because Jane did like her nipples pulled and pinched very hard. I thought what the hell, after all I did fist her pussy and ass at the same time and she loved that! "Okay, it all makes sense. You two should have Jane show you our Hawaii video! That one will shock you! How do you want to do this?"

We all sat up on the bed and looked at Jane. She thought a moment and then said, "Well, in my fantasy I get turned over your knee and you give me ten or twenty good hard slaps on my ass and then I lay on my back and you pound my ass like there's no tomorrow."

"You realize I have had anal sex twice today already so I'll probably last a long time." I said.

Jane smiled and kissed me then said, "I'm counting on it! I love it when you pound my ass for a long time. Remember the time when we first moved into the house and we shoveled the snow? I loved that! I was so worn out he had to carry me upstairs to our room! I want that again!"

Debbie and Denise laughed and then Denise asked, "What would you like us to do?"

Jane replied, "Whatever comes naturally! I love an audience so you can just watch if you want. All I know is that I'm going to get royally fucked! So, Tony, pull that chair over and sit in it and I'll lie across your lap and you can spank me. When I say...uh, banana, I want you to stop spanking me and throw me on the bed where you'll fuck my brains out! Okay?"

"Okay. Come on over and get across my lap."

Before I started Debbie came over and gave me pointers on where and how to slap Jane's ass. When I had it I asked Jane, "Are you ready?"

I looked down on Jane's beautiful porcelain cheeks and rubbed them lightly for a few moments before I lifted my hand and brought it crashing down with a loud slap. The sound seemed to echo around room and when I lifted my hand there was a perfect imprint of it on her right cheek. Jane gave out a low groan and whispered, "Oh Yes!" I lifted my hand again and brought it down again, this time on her left cheek. Her cheek jiggled nicely when I had smacked it. There was now another handprint on her left globe. I began spanking Jane with a constant tempo alternating cheeks and spreading the wealth from the top of her but down to the tops of her legs. I spanked her five, ten, fifteen, twenty times and she still hadn't cried out banana. My hand was getting a bit sore but I kept up the spanking. Finally, at thirty-one Jane cried out banana.

I lifted her from my lap and placed her on the bed. I called to Denise to give me the KY but Jane called out, "No, just use my pussy!" I knew that she liked anal sex with minimal lube sometimes and, apparently, this was one of those times. I pushed her legs back and fucked her pussy for a minute and then pushed her legs back further and pushed into her waiting asshole. I pushed in hard all of the way in one hard stroke and began pounding her ass as hard as I could. Jane looked into my eyes with her beatific look and a smile on her face. She had an orgasm after a couple of minutes because I felt my balls get wet and my dick got slick from her ejaculate.

Debbie lowered her head down and kissed Jane for a couple of minutes but Jane pushed her away so she could watch my face as I continued to pound away. I felt Jane climax several times and finally I started to feel mine begin to rise up. At this particular moment, I felt something wet on my own sphincter and then a finger sink in real deep and begin to touch my prostate. The few times Jane did this to me I thought I was going to shoot my balls out of my dick. I then felt a second finger sink into my ass and with that I growled and exploded into Jane's bottom. Stream after stream sprayed into Jane as I grunted and groaned. Jane held me tight against her as she too was having a massive orgasm. I wanted to roll off of her but she whispered, "Stay in me please."

We stayed linked for ten or so minutes before Jane let me go. I rolled off of her and pulled her into my arms. We laid together for another ten minutes before I asked, "So? Was it what you wanted?"

"My god, Tony! I must have cum twenty times, five while you spanked me! It was so intense, it was awesome! You were incredible as you always are. I love you so much I can't begin to express it!"

"Who's finger went up my ass?" I enquired.

Denise said, "That was me. Jane said I should do it to you when you looked ready to cum."

"Well, your timing was perfect! I thought I was going to shoot a testicle out of my cock!"

The four of us laid around on the bed for the remainder of the afternoon and talked. Debbie asked, at one point, about the Hawaii video. I chuckled, grabbed my phone and then played the video for them. They sat there with their mouths agape while watching it. They played it three times (a new record) before they stopped.

Debbie asked, "What possessed you? A whole hand in your ass?"

Jane laughed and said, "That was nothing. Down on the beach I had one of his hands in my ass and one in my pussy!"

I saw Denise squirming a bit so I asked her, "So, what do you think?"

Denise blushed and said, "I think the idea of a fist in both holes sounds pretty fucking hot! I wouldn't mind trying that. I get pretty close to all of my hand in my pussy when I masturbate, sometimes."

Debbie looked at her friend wide eyed and asked, "You really want to try that?"

Denise smiled and nodded. Jane sat up, looked at me and said, "You are right! I've created a monster!" She then laughed as did Denise and I. Debbie was shaking her head in amazement.

Debbie then said, "Do you want to do this now?"

"Yeah, I would."

"Whose fist would you like?" Debbie continued.

"Tony's if he doesn't mind. Jane managed it with him so I think he's the logical choice."

"I don't mind if you are sure you want to do this."

"I'm sure! My pussy is soaking wet just thinking about it"

I was beginning to think that Denise and Jane were twins who were separated at birth. They were so alike in so many ways. I felt a genuine attraction to Denise because of it. I said, "Denise, you will need to clean yourself and we should get some towels and put them on the bed because this gets pretty messy because we use a lot of oil. Also, if Denise squirts like she did yesterday the hotel will thank us!" Jane got up and gingerly walked to the bathroom for some towels. I could see that her ass cheeks were still pretty red. She also got some coconut tanning oil from our bag. Denise and Debbie headed into the bathroom to take care of Denise's backside.

Once Denise was cleaned out I had her get into a sort of fetal position while on her knees on the edge of the bed and then I pulled Jane's spanking chair up so I was sitting right behind her. I placed one of the towels on Denise's calves and draped one across my lap. "So, where would you like me to start?" I asked.

Denise answered, "My ass please."

I poured some oil on Denise's ass crack and let it run down until it hit her anus. I saw Denise shiver a bit as the oil trickled down. I handed the bottle to Debbie who was standing next to me watching with rapt attention and told her what I needed her to do. Jane crawled up on the bed and laid down so her face was in front of Denise's face and began kissing her. I began to work the oil around with my right-hand index finger and pushed my finger in slowly working it all of the way into Denise. I told Debbie to pour some more oil on my hand so that my fingers got coated and the pressed my middle finger in joining my other digit. I pushed into her all of the way while twisting my fingers around as I began to stretch the muscle. A few minutes later I pressed in a third finger and then a fourth.

Denise was moaning pretty loudly into Jane's mouth so I asked her if she wanted me to stop but she shook her head no. I told Debbie to pour more oil onto the back of my hand and to rub it on up to my wrist. When Debbie had finished, I moved my thumb into the palm of my hand and began to press my knuckles into Denise's rectum. I pushed in and pulled back forcing my way in in tiny increments slowly working my hand inside of her. When the widest part of my hand was stretching her hole, Denise pulled off of Jane's mouth and cried she was cumming. I lowered my head down to Denise's vagina just in time to catch her girl cum in my mouth. I loved doing that with Jane and I loved it now with Denise.

I resumed working my way into Denise's backside and once I got passed my knuckles I began to slip in pretty easily. I couldn't believe how stretched out Denise's asshole was. Once I was in up to my wrist I began fucking her ass with my hand with short strokes pulling out to the widest part of my fist and then pushing back in. Denise lifted her head from Jane's and cried out, "OH FUCK! THIS FEELS SO REMARKABLE! TONY! PUT YOUR OTHER HAND IN MY PUSSY!"

I held my left hand to Debbie and told her to rub oil all over my hand like she did the other. Once I was oiled up I began working my left hand into Denise's soaking pussy. As soon as I got my third finger into her she cried out that she was cumming again and squirted on my arm and onto the towel in my lap. I worked my four fingers into her and worked them around, again stretching her out for my final assault. I brought my thumb into my palm and worked my hand all of the way into Denise's vagina. I began pumping my hands alternately in and out of Denise's holes. I told Jane to play with Denise's clit while I stroked her holes. Within minutes Denise began to orgasm again and again! After about her sixth or seventh climax Denise said that she had had enough so I began extracting my hands from her orifices. When I had my hands clear, she turned over onto her back with her legs splayed wide open.

While she panted, Denise said, "That was amazing! I just kept cumming and cumming! Thank you all so much for letting me do this. Jane, you are an amazing kisser! Debbie, I hope you learned how to do this because I will want you to do it to me! Tony, you are the most amazing man I have ever met! If you ever want to start a harem I'll be happy to be your second wife after Jane. I love you all so much!"

I leaned down and kissed Denise and then I went to the restroom to wash my hands. When I returned to the bedroom I suggested that we get dressed and get some dinner, since we had skipped lunch. Everyone nodded in agreement. Since we all wanted to take showers and we were a couple of towels shy I called down to have some towels sent to our room. Jane and Denise were in the shower when the towels arrived. Debbie and I took to the shower once the other two were finished. When everyone was dressed, we all went downstairs to eat. Jane was moving a bit slowly and walking a bit stiff legged and Denise looked like she was feeling a bit tender. We had a nice dinner, though everyone was a bit subdued.

When we got back to the room, all of the women stripped their clothes off but nobody was suggesting anything sexual. I think they were all, finally, sated. We all turned in early with Jane back in my bed. Jane and I kissed and cuddled for a while until Jill turned around and spooned back into me. We both fell asleep rather quickly...

The next day dawned bright and sunny and I was happy about that because Jane and I were going to resume our road trip. When we got our various vehicles repacked, we bade Debbie and Denise goodbye with lots of hugs and kisses. Before we parted, Jane got both of the women's cell phone numbers so we could stay in touch.

When we were, finally, back on the road we headed south so that we could take in the Grand Teton range for the day. Jane had resumed her naked passenger mode and seemed to be back to her chipper self after a subdued evening the night before. After some small talk Jane asked, "So, what did you think of Debbie and Denise?"

I knew this question would come up eventually so I had my answer ready. "I like them both. I especially liked Denise because she reminds me so much of you. You both have similar bodies and are both fearless when it comes to sexual experimentation. I like Debbie too but Denise kind of got to me in a good way. The odd thing was that, though both of them are several years older than we are they both seemed younger."

'I noticed that too, though I don't know why that is. They seemed to let us take the lead in everything. Well, I love them both and I hope we can spend a lot of time with them later on."

I agreed with Jane, I would like to spend more time with them because they were fun and bright. Though the drive to the Tetons is fairly short from Yellowstone, we decided to camp there so we could admire the view for an extended amount of time. They are magnificent mountains! We found a camping place and since it was a weekday it was sparsely occupied and busied ourselves with setting up our camp. Once we were all set up I set about preparing lunch from some of the provisions we purchased in Jackson. We ate our lunch while we sat and admired our view of the mountains.

When we went to bed that evening, Jane straddled my face while she sucked my cock. It was nice to be with Jane alone. As much as I enjoyed having sex with Astrid, Denise and Debbie I was always happy to be alone with my one love. We enjoyed our romp together without an audience and then slept soundly until the chattering birds woke us up.

In the morning, we had a quick breakfast and coffee before setting off once again. Our objective was to get to Mt. Rushmore and the Black Hills of South Dakota. Jane, once again, stripped her clothes off while I drove. For a short period, we were on an Interstate highway out of Casper, Wyoming. Jane's exhibitionist side was in full bloom as several truck drivers got an eyeful of her beautiful body. I think it really started to excite her because, after a while, she reached in and grabbed her large butt plug. She inserted it just as we passed a very slow moving truck on a steep hill. Since our VW wasn't exactly rushing up the hill, it took several minutes to get past the truck. She pushed the plug in and out of her ass while she played with her clitoris. I know I had a giant erection and couldn't imagine what the truck driver was going through.

After a while we were back to two lane highways and no more opportunities for exhibitionism. After a while Jane leaned over and kissed my ear and whispered, "Pull over as soon as you can. I need you to fuck my ass!" Since I was still sporting my erection from the Interstate, I was more than willing to satisfy Jane's needs. I saw a small 'pull-off' just off the road and darted into it. Jane climbed through to the back of the van and stopped at the edge of the bed with her ass pointing at me. I grabbed the tube of KY from the glove box, popped the rooftop up, dropped my shorts, slathered my erection with the lube and then pulled Jane's butt plug out. Once the plug was clear I replaced it with my cock and drove into Jane's ass fast and hard.

It was a little weird having sex as cars zoomed past on the highway, but we were both pretty horny. It didn't take long at all for us both to climax and before long we were back on the road again. We made it to the Black Hills in the late afternoon and quickly found a camping spot. We made dinner and ate alfresco enjoying the smell of the trees and the fresh air. After dinner, we showered and got ready for bed and then turned in for the day.

The next day we visited both Mt. Rushmore and the Crazy Horse monument. We were very impressed by the massive size of both monuments. By the time we got back to our camp it was still early afternoon so we decided to take a hike through the woods after we ate some lunch. It was a sunny hot day and since nobody was around Jane decided to peel of her shirt and shorts. I walked behind her and admired the view ass her ass jiggled with every step and before long I was sporting quite the erection. When we came to a rock outcrop Jane said we should go behind it because she wanted me to fuck her.

I laid on the ground after I had dropped my shorts and Jane climbed on top of me and sank my iron hard penis into her sweet vagina. As Jane rode me I grabbed her tits and pinched her nipples the way she liked it. Jane had had a couple of orgasms and I was closely approaching mine when a female Ranger walked around the rock to where we were. Jane was oblivious and kept fucking me with abandon until she heard the Ranger speak. Jane whipped her head around at the sound and stopped what she was doing.

"There is no rule that you can't have sex in the woods but you really should be a little quieter." The Ranger said. "Actually, you might want to return to camp because there has been a bear in this area with cubs that has been causing some problems. I apologize for interrupting your fun."

Jane stood up and began to put her shorts and shirt on while the Ranger gave her an admiring once over. I was still quite hard because I hadn't cum yet so struggled to get myself into my shorts. While I struggled, I thought I noticed the Ranger lick her lips quickly. The Ranger said she would escort us back to the campground in case the bear appeared. We introduced ourselves and found out the Rangers name was Anne. We asked her about being a Ranger and she asked us what we did. It turned out that not only had Anne graduated from our school but she was a lit major as well. We asked her if she knew Pearl and she went on to say that Pearl was the best professor she had ever had. She laughed with surprise when we told her she was our neighbor.

When we got to our van we sat and talked to Anne for quite a while. She was very interesting and had great stories to tell about her job in the Black Hills. Jane said, "I suppose our little tryst in the woods will make it to the pantheon of your tales?"

Anne laughed and said, "Of course it will! I have never found anyone having passionate sex in the woods like that! The names will be changed to protect the innocent, by the way." Jane and I laughed and let out exaggerated sighs of relief. Anne stood up and said she had better get back to work. "I would really like it if you two would join me for dinner tonight. My place is the house at the entrance to the campground. Say, around 7?"

Jane and I agreed that we would come by around 7. After Anne left Jane said, "Wow, imagine meeting an alum out here. She was pretty good looking too, didn't you think?"

"Yeah, she was quite lovely, especially if you go for women in uniforms!" I joked.

"Seriously, I thought she was quite beautiful. I look forward to talking to her some more tonight. We should give her our address and phone numbers so if she's ever in Chicago we can reunite her with Pearl."

"That's a good idea. I bet she has some good Pearl stories for us! I think we should get in the van and finish what you started! I'm still hard!"

"Yeah, I know. Anne kept sneaking looks at your crotch while we talked!" Jane added.

We got into the van and resumed our love making causing the van to rock around a bit. When we were finished, we grabbed some clean clothes and headed over to the showers to get cleaned up for dinner at Anne's. Since we weren't dining at a restaurant we decided to dress in our usual, casual way. I had on my regular khaki shorts and t-shirt and Jane had on some loose shorts and a very thin tank top. I loved when she wore that shirt because it did nothing to control her breasts as she walked. They jiggled and bounced around with very step and her nipples always got hard because the material would rub them as she walked.