Summer Break with Jane and Tony Ch. 01

I couldn't believe what was happening. I was going to have an 'Astrid' weekend all over again but with an extra girl! I couldn't imagine how I was going to be able to please 3 women all at once. I did have to admit that Debbie and Denise were both beautiful. Debbie was built along the same lines as Astrid, thin and lean but blonde. She had small breasts but her nipples were quite long and hard. Denise, on the other hand, was built more like Jane, soft and round. She had really large areolae and big hard nipples. Both women had bald pussies and both of them were quite swollen and damp with excitement. Having three beautiful, naked women in the room with me gave me an erection for the ages.

I stood up and pulled my shorts and shirt off as Jane hugged me. She then kneeled down and took my erection into her mouth. I just stood there and moaned as I enjoyed how Jane's mouth felt on me. I looked over at the other two women and they just stood there in amazement as Jane sucked on me. After a minute or two Debbie decided to join in and got on her knees behind Jane and began running her tongue up and down Jane's ass crack and pussy. This got Jane moaning and I could feel the vibrations on my penis as she did. Denise decided she didn't want to be left out so she walked up to me and began kissing me.

After a while Jane pulled me from her mouth and said, "I need you in me Tony! Lie down on the bed so I can straddle you. One of you can sit on his face if you want, he's a terrific pussy licker!"

I laid down and Jane crawled up on me and sank her wet pussy down on my cock. As Jane began pumping me in and out of her Denise decided to take Jane up on her offer of my face. She lowered her swollen pussy down over my mouth and I took a tentative lick. Denise's aroma and taste were different than Jane's and Astrid's but was delectable. As I began giving Denise's vagina my full attention I could feel her squirming and grinding herself on me. "OH FUCK! DEBBIE, YOU NEED TO HAVE TONY EAT YOU! HE'S BETTER AT IT THAN YOU ARE," Denise cried out! Debbie didn't reply because I could feel her tongue licking my cock as Jane lifted herself up as she fucked me.

"LICK MY ASSHOLE DEBBIE! OH, YEAH, JUST LIKE THAT," Jane called out!

All of a sudden Denise cried out that she was cumming and I could feel her quivering as she came. When her climax was over she rolled off of me and called for Debbie to take her place. Before Debbie came around to take her place, Denise gave me a deep tongue filled kiss and then sat up and thanked me for a wonderful orgasm. Debbie then leaned down and kissed me before straddling my face. Before lowering herself, Debbie did something a little different and reached down and pulled her pussy lips apart showing her pink and her vaginal opening. She was, literally, dripping wet as several drops landed on my face. I reached up, pulled her down and then buried my tongue into her hole as deep as I could. Debbie let out a deep groan as I began working on her pussy. Again, I detected the subtle differences in aroma and taste and found her as enjoyable as the others I had experienced.

Jane was, by now, really rocking on my cock and called out that she was going to climax. I felt her soak my pelvis with her ejaculate and felt her quiver and shake as her orgasm hit her. Jane rolled off me and she told Denise to take her place. Denise said that she was still recuperating from her earlier climax so Debbie crawled down my body from my face and then sank my erection into her sodden pussy. Debbie let out another moan as she sank all of the way down my shaft. As she lifted and lowered herself her tight, thin ass was spread nicely so I could enjoy the view of her pretty pink anus. I stuck my index finger into my mouth to get it good and wet and then pushed it, slowly, into Debbie's asshole! She moaned again and looked over her shoulder and gave me a devilish smile!

Jane, watching what was going on, laughed and said, "If you like that, wait until he sinks his beautiful cock in your ass!"

I was beginning to feel my orgasm raise its head and announced to Debbie that I was going to cum real soon. She acknowledged that she was too and began redoubling her effort on my cock. I began thrusting back up to her as she lowered herself when, all of a sudden, Debbie began shaking as her orgasm hit her. I could feel her vaginal walls squeeze me which sent me over the edge as I buried myself as deep as I could in her pussy and let loose with my load of semen! Debbie ground herself on my cock as we both enjoyed the sensations rippling through our bodies! Finally spent, Debbie laid back onto my chest as we both gasped for air. I reached around and hugged her body to mine as we calmed down. I felt one of her nipples so I lightly pinched it as we laid there.

When my cock fell out of Debbie's pussy Jane asked, "Do you mind?" and without waiting for an answer buried her face in Debbie's oozing pussy and began licking out my deposit. Debbie's breathing got fast again as Jane ate my cum from her pussy so I decided I would contribute to the effort and began pinching both of Debbie's nipples fairly hard. Before long Debbie cried out that she was cumming again. Jane must have been really going to town on Debbie because I think she had several orgasms before she rolled off my chest begging for mercy.

Denise was sitting on the bed stroking her pussy while all of this was going on. "Oh my god! That was so hot!" Denise said. "I've never seen anybody suck the cum out of a pussy before! I have to try that!"

I got off of the bed and told Jane that I wanted to take a shower and then we should go downstairs for dinner. Jane asked, "Can we join you? Is the shower big enough?" I looked into the bathroom and reported that it was pretty small so room enough for two people max. I turned on the water and began washing myself as Debbie came in.

"I was elected to shower with you. I want to thank you for the wonderful orgasms. Is it weird for you having sex with two complete strangers?"

I told her about how Jane and I met and had sex for the first time at Thanksgiving and how she was the only woman I had had sex with. Then I explained about Astrid's visit a few weeks ago and that she was my second person. "If you discount the Bill Clinton theory that oral sex doesn't count, Denise was my third and you were my fourth. So yeah, it's a little weird but I'm adjusting. Besides, every one of you has been beautiful so I really don't mind!"

"Thank you for the complement. You're pretty easy on the eyes too!"

I bent down and kissed Debbie and she pulled me into a hug as we kissed. When we broke the kiss, we laughed and proceeded to scrub each other. We were just climbing out of the shower when Jane popped her head in asking if we were done yet.

"We just need to dry off. You and Denise can't start anytime."

Debbie and I finished drying ourselves and then went into the room where our luggage was. As we dressed Debbie said, "Jane is quite a girl! She's tops in her class in the lit department. She said that Denise and I helped her but in reality, she requires nobody's help academically."

I smiled and said, "Yeah, she's pretty bright. We are both holding down 4.0 GPA's so we have a bit of a friendly completion going to see who cracks first. I'll probably crack before her, she has no fear."

Debbie smiled and nodded, "I gather she's the extrovert when it comes to sex? When she yelled for me to lick her ass I was taken aback a little. Before you put your finger in me, I had never had anything up there other than a thermometer!"

I winced then said, "I'm sorry! I can get carried away sometimes. I hope I didn't hurt you. Jane really loves anal play and anal sex so I just carry on like that is normal for everyone. Please forgive us if we caused any discomfort to you."

Debbie smiled and then came over and kissed me. "You are such a sweet man! Please don't worry, your finger felt quite nice and the orgasm I had after you inserted your finger was the best, most intense one I have ever had! It kind of makes me curious about anal sex now."

I laughed and said, "Don't let Jane know you are curious! She'll make us drop everything and have me in your butt before you can say 'yankee doodle'! If you do decide you want to try it anal with me, then tell Jane and she will fix you up. But don't feel pressured."

At about that time Jane came popping out of the bathroom asking, "Why is Debbie feeling pressured?"

"Debbie and I were talking about sightseeing the next few days and I told her that she and Denise shouldn't feel like they have to go with us if they don't want to. But we would love it if they did accompany us." I lied.

Debbie smiled and said, "I was just telling Tony that I didn't want to be a burden on you two."

"You and Denise aren't a burden!" Jane replied. "We love sharing!"

When everyone was dressed the four of us made our way to the restaurant. We had a splendid meal and then went for a walk and managed to watch Old Faithful erupt one more time. While watching the geyser, Jane said, "This is going to sound weird but that makes me really horny!"

"Everything makes you horny!" I replied.

Jane laughed and said, "Yeah, that's true! Well, I'm ready to turn in. Are you ready to satisfy three beautiful women, Tony?"

'I will give it my best effort but I may require some help!"

We all laughed and headed up to the room. As soon as the door closed Jane's clothes were off. I never tired of looking at her naked splendor. In close second was Denise whose body looked a lot like Jane's. My penis was now wide awake and ready for action. Lastly, Debbie stripped and then me.

"Denise hasn't had Tony's lovely cock in her pussy yet so I think it's time she was taken care of," Jane said. "Debbie, why don't you lean up against the headboard with legs spread. Denise, you get on your hands and knees so Tony can take you from behind and you can have Debbie for dessert!"

Debbie said, "But what about you?"

"I'll just wander around and help out!" Jane replied. "Tony, perhaps I should get Denise in the mood for you."

So, Debbie crawled up the bed, turned and leaned against the headboard with her legs splayed wide open. Denise crawled on her hands and knees and began licking Debbie's vulva while Jane crawled upon behind Denise preparing her pussy for my penis. I have to admit I was enjoying the sight. Both Jane's and Denise's large full breasts were hanging and swaying as they licked their assigned pussies. Debbie, who had small breasts but large hard nipples was pinching and pulling those nipples as she was being eaten. All three women were in similar states of bliss. I think if it came to it, women would manage fine without men in the world...a chilling thought!

Finally, Jane called to me and said Denise was ready. I crawled up the bed and gave Jane a deep, passionate kiss, tasting Denise on her lips and then turned and placed my cock between the lips of Denise's pussy and slid it back and forth getting some of her dew on me. I then aligned myself with her vagina and slowly, but steadily, slid into Denise's womb. Denise was quite wet and quite a bit tighter than Jane or Debbie. We both moaned with satisfaction as I slid into her.

"Denise, you feel quite tight." I rasped out

She lifted her head from Debbie and said, "Yours is only the second penis I've had in me. It feels wonderful, by the way. It has been so log since I've been fucked by a man! Could you do what you did to Debbie and put a finger in my ass?"

Hearing Denise's request Jane said, "I can do that for you!" Since she was still kneeling beside me, Jane shifted around and drug her finger through her own sopping pussy and then slowly pushed her index finger into Denise's anus. I was pumping into Denise with a nice steady tempo while Jane matched my tempo with her finger. Denise, with her face being pulled into Debbie's quim by Debbie, sounded like she was trying to talk but everything was coming out garbled. After a few more minutes, Debbie announced that she was cumming and let go of Denise's head. At about the same time Jane decided to insert a second finger into Denise.

"OH, FUCK! OH, FUCK! THAT FEELS SO GOOD! FUCK ME HARDER!!!" Denise cried.

Jane and I both increased our tempo. I was pounding into Denise's pussy as she cried out that she was cumming. I felt her pussy squeeze me and I felt Denise shaking but I kept pumping into her as did Jane. Denise had several more orgasms before falling flat on the bed causing my cock to pull out of her pussy. Jane saw that I was still hard and hadn't climaxed and she saw that the other two weren't about to take advantage of the situation so she got on her hands and knees and told me to fuck her ass.

My cock was dripping with Denise's juice and Jane reached back and spread her saliva on and in her asshole as Jane said, "Fuck my ass please, Tony!" Who could refuse such a polite request so I put the head of my cock against Jane's rosebud and slowly pushed in. I loved fucking Jane's ass and I knew what she liked. As soon as I got all of the way into her I pulled back most of the out and then pushed right back in with no hesitation.

"YES, TONY! YES! FUCK MY ASS! FUCK IT HARD, TONY!" Jane cried out.

The other two girls quickly revived themselves and got up on their knees to watch Jane get her ass pounded. I yelled to them, "DEBBIE! PLAY WITH JANE'S CLIT! DENISE! PINCH AND PULL ON JANE'S NIPPLES HARD!" Both women jumped to action immediately doing as I instructed. Jane reacted immediately as both women further stimulated her. Jane had her first orgasm of the evening shortly after Debbie and Denise got to work. Debbie cried out in surprise as Jane released her ejaculate during her climax. I kept pounding into Jane and felt the beginnings of my own orgasm waking up. A couple of minutes after her first orgasm Jane came again releasing more of her fluid on Debbie. Finally, my own climax was upon me and I cried out that I was cumming. I thrust into Jane's bowel as deep as I could and then released my seed into her darkest depths! I shot rope after rope of my jism into Jane's backdoor. Jane then collapsed onto the bed and I followed her lying on her back still impaling her ass.

Finally, after we were back to normal Jane said, "Tony, you need to pull out of me so one of these ladies can suck the cum out of my ass!" I laughed and rolled off of Jane pulling my cock out of her ass. Both girls looked at one another, then at me and then at Jane's ass.

"It's quite alright," I said. "She cleans herself immaculately all of the time."

Debbie raised her eyebrows and then dove in pulling Jane's cheeks apart. Denise decided to help by straddling Jane's back and pulling Jane's cheeks to help Debbie. Debbie lifted her head and told Denise to give it a go. Denise buried her face in Jane's ass crack and began slurping. The two women seemed to be enjoying themselves. When finished they both, tumbled down on the bed and we all lay there collecting ourselves. After a while Debbie smiled and said, "Tony, you taste pretty good."

"You taste pretty good too, both of you!" I replied.

I decided I had had enough for the night, got up and went to the bathroom to brush my teeth and get ready for bed. Jane wandered in after a while and brushed her teeth too. When we had finished, Debbie and Denise did the same thing. When all of the lights were out and everyone was in bed Jane called out goodnight to Denise and Debbie. They wished us a goodnight back. Jane then kissed me and said that she loved me and I told her I loved her too. Jane turned her back to me and cozied up against me and we fell asleep.

In the morning, the four of us went to breakfast and decided on our itinerary of sightseeing. We decided on several sights to see and a day hike. We bought provisions for lunch and filled a couple of daypacks and then set off. We saw the 'boiling mud pots' and a couple of other geysers before we made our hike. All in all, it was a great day with great company. Denise was very knowledgeable about the flora and fauna we had seen during the course of the day. We arrived back at the lodge rather late so we decided to get a quick dinner before we returned to our room.

Once back in the room we all wanted to shower and decided to do it in pairs. Debbie and Jane went first so Denise and I would follow. I said to Denise, "You know, it will probably take a while for those two to finish, if I know Jane."

Denise laughed and said, "Yeah, Debbie is the same...always horny! Do you mind if I ask you something?"

'No, go ahead." I replied

"Well, after watching you and Jane, you know, um, uh, have, you know, anal sex, and seeing how much Jane liked it, well, uh, well it made me curious. How did you two discover it?"

"Years ago, Jane caught her parents doing it." I replied. "She didn't see them but heard them through their door. They were both rather loud as they were in the throes of passion and they both seemed to be enjoying themselves...a lot! Jane began researching it online immediately and, over time, experimented while she masturbated. Last year, on the weekend we first had sex together, Jane asked if we could try. I hadn't a clue about such things as I lived a cloistered life in a catholic orphanage. That weekend was the first weekend I had ever kissed a girl, let alone have sex.

"I was pretty astonished that Jane wanted to try it but she was adamant and I was of the mind that I would do anything she wanted. After she prepared herself we took a shower and then did it there in the bathroom."

Denise sat thinking for a moment and then said, "I gather you both liked it. What was it like for you?"

I smiled and replied, "Remember, I was very inexperienced at the time, but it was the single most erotic thing I had ever experienced."

"Why?" Denise asked.

"Well, imagine Jane bent over with her arms on a bathroom vanity. Her breasts swaying with each trust of my penis, her bottom rippling as I bottomed out, her skin glistening with the water of our shower and my penis stretching her tiny little anus. The intensity of the heat and tightness of her rectum on my penis was incredible. The whole thing was so much different than vaginal sex or oral sex. It added another dimension to our love life."

Denise sat glassy eyed for a couple of moments before uttering, "Wow! I really think I would like to try that! Would you be willing to have anal sex with me? I know I'm asking a lot of you, but when you guys put your fingers in my ass I really liked it. I don't want to ask too much of you and Jane. It seems to be a very personal thing to do."

I chuckled and said, "I think it's Jane's personal crusade to spread the word of the glories of anal sex. If you really want to try it, we will be more than happy to be a part of that. Do you want to do it tonight?"

"Oh, yes! Do you think we can?"

"When Jane gets out of the shower tell her what you want to do. She will give you an enema to clean out your bowel and then you and I can shower together. When we finish our shower, we can then get you ready and do the deed. Okay?"

'Oh, yes! Thank you so much, Tony!"

Denise then tackled me laying me flat on the bed with her on top of me and she began kissing me deeply with passion. We were both still dressed as we made out. After several minutes Jane cleared her throat and said, "What's going on here?" as she laughed. Denise rolled off me with a look of guilt on her face. Jane laughed again at Denise's guilt ridden face and said, "Oh, Denise, I was kidding! As long as we are here Tony belongs to all of us!"

Dense smiled and then said, "Thank you, I was afraid I angered you. Tony and I were just talking and I was thanking him. He agreed to have anal sex with me and he told me you would help me get ready. Would you mind?"

Jane's smile could have lit up the room. "I would be more than happy to help you get ready! Let's get you cleaned up!"