Summer Break with Jane and Tony Ch. 01

"Tony said that you would give me an enema and then he and I could shower before we proceed. Is that right?"

Jane smiled and said, "Yep! Get you bum in the bathroom!" Then looking at me, Jane said, "I'll come get you when it's shower time. Have I mentioned that I love you lately?"

I laughed and told Jane I loved her too. Jane and Denise went into the bathroom and as they went through the door Jane called out to Debbie to accompany them. I laid back on the bed and thought about what I was about to do with Denise and I smiled. She was built so much like Jane and she was such a sweet woman I was looking forward to exploring anal sex with her. I could hear the three women in the bathroom since they hadn't closed the door. It sounded like they were having a party in there.

Finally, Jane and Debbie left the bathroom and I could hear the shower had been turned on. I stripped off my clothes and made my way to the shower. Before I got there, Jane grabbed me and kissed me deeply before letting me enter. Denise was in the shower already and looked beautiful as the water glistened on her skin. As I stepped into the shower, Denise pulled me into a bone crushing hug and kissed me deeply and passionately.

"Tony, I can't thank you and Jane enough for everything you have done for Debbie and me. You are both so loving and giving. Thank you from the bottom of my heart."

I could see tears developing in Denise's eyes so I kissed her sweetly and said, "Denise, we love sharing our love with our friends. You are beautiful as is Debbie and nothing gives us more pleasure than being with and sharing with friends." She smiled and released me from our hug and then we proceeded to wash each other thoroughly. Once clean we dried each other off and then made our way into the bedroom. Jane and Debbie were sitting on the bed waiting for us as we walked in.

Jane said, "I think it would be best for Tony to take you from behind, Denise. Why don't you get up on the bed so your feet are hanging off the edge and Tony can stand behind you. But first, Debbie and I will get you ready, if that's okay?"

Denise nodded nervously and got onto the bed as instructed. Apparently, Jane and Debbie had discussed plans for readying Denise and they both jumped into action. Debbie kneeled down behind Denise while Jane spread her ass cheeks wide. Debbie then dove right in and began licking and prodding Denise's anus with a vengeance. I sat and watched while Denise was prepared with tongues, fingers and then, finally, an ample application of KY! Jane announced that Denise was ready and that I should come over.

As I walked over to the bed Debbie squirted a large amount of the lube onto her hand, reached for my cock and then slathered it all over my length. As she did that, Jane worked her way under Denise so her face was directly under her pussy and began licking. When I was deemed adequately lubed I was allowed to walk up behind Denise. As I looked down to grab my penis to position it at Denise's asshole, I saw Jane's smiling eyes as she winked at me. This caused me to smile as I slowly began entering Denise's rosebud.

Denise's anus was very tight and it was a bit of a struggle getting into her, but, finally, the head of my cock popped into her backdoor. No sooner had I penetrated her Denise cried out, "OH, FUCK! OH, FUCK! I'M CUMMING!" I couldn't believe she came so fast and neither could Jane!

"This is going to be good! She just squirted a gallon of cum on my face!" Jane cried out.

I waited until Denise's climax ebbed before pushing further into her depths. As I pushed in incrementally Denise moaned, groaned and cried out "YES! YES! MORE! MORE!" When I sank myself all of the way into her ass I paused to let Denise get used to things but she cried out that she was orgasming again! I couldn't believe my ears! Could Denise love anal more than Jane? The thought was mind-blowing!

Once Denise's second orgasm waned I began fucking her with a nice, slow easy tempo. Her tightness felt wonderful as I savored every centimeter. After a while she began to move into me as I pushed in. Denise cried, "DEBBIE! YOU HAVE TO TRY THIS! IT FEELS SO WONDERFUL! OH, FUCK! I'M CUMMING AGAIN!" I could feel Denise squirt her ejaculate as it hit my balls. I couldn't imagine what Jane was going through with her face in Denise's pussy! When the squeezing pressure on my cock relented, I began thrusting into Denise once again. As I thrust Denise began pushing back harder and harder. Taking my cue from her I began fucking her faster and harder until I was pounding into her ass.

I could feel my own climax begin to build and cried out, "I'M GOING TO CUM!" as I continued pounding Denise's ass. Denise cried out that I should cum in her ass and after a couple of moments I let out a guttural moan and began shooting my spunk into the depths of Denise's bowels. As soon as I felt my release Denise cried out that she was cumming. I could feel her rectum squeeze me as I pumped stream after stream of my sperm into her. It was one of the most intense orgasms I had ever experienced.

When Denise's orgasm finally quieted, she rolled off to her right onto the bed off of Jane and pulling my dick out of her with a plop. Jane, seeing my cock right in front of her grabbed it and pulled me into her mouth and sucked any residual come off of and out of me. I couldn't take too much because I was feeling quite sensitive so pulled myself from her mouth and collapsed onto the bed on Jane's other side. Denise and I laid there panting as we recovered from our ardor. Three of us were on the bed while Debbie stood with her mouth agape in disbelief. Jane rose from the bed, her head and faced soaked from Denise's orgasms and went to Debbie and asked, "What did you think? Do you want to try it?"

Debbie shook herself from her stupor and said, "My god! That was awesome! If it's half as good as it looked I'm in!"

Jane laughed and said, "Well, by the looks of Tony it will have to wait until tomorrow. Denise, how did you like it?"

Denise sat up while leaning back on her arms and said, "I may never have vaginal sex ever again! It was totally, fucking awesome!" She then crawled over to me and kissed me deeply. When she broke the kiss, she looked into my eyes and said, "Thank you, Tony! That was the most incredible experience of my life and I will never forget you and Jane for giving it to me! I love you both deeply!" Denise then bounded out of bed and gave Jane a huge kiss and hug. When she broke the kiss she finally noticed the state of Jane's hair. "Did I do that?" she asked with astonishment.

Jane laughed and said, "Yes you did! I now know what it's like to be water boarded!"

We all laughed as Jane headed for the bathroom for another shower. As she got to the door she stopped and said, "Denise, why don't you sleep with Tony tonight. I think Debbie and I are kind of horny after your display and may have to work some of that out of our systems tonight!" I sighed a sigh of relief while both Debbie and Denise smiled. I crawled under the covers and held them up for Denise to join me. She climbed in and laid down about two feet away with her back towards me. I grabbed her torso and pulled her towards me. She turned and kissed me again deeply and then spooned up against me. My arm was draped over her side so she pulled it up to one of her breasts and held it there. I smiled to myself and fell asleep.

When I awoke in the morning I remembered that it was Denise next to me and not Jane. What awoke to was the feeling of Denise rubbing my engorged penis in the crack of her ass. I ventured to utter a whispered good morning. She replied with a good morning and said, "Would you fuck my ass again, please?"

"Right now?"

"Yes please. Do you mind?"

"No, I don't mind at all. Are Jane and Debbie still asleep?"

"Yes, they were at it until quite late. You girlfriend is pretty insatiable from what I can tell!"

I laughed and said, "Yeah, I can attest to that! How do you want to do this?"

"Just like we are, if that's okay? I have the lube ready to go."

"Alright, lube us up!"

Denise fiddled around a bit and then I could feel her reach behind her between us and apply the lube to herself. When she was done she then applied lube to my erection. When she was satisfied, she grabbed my cock and lined it up with her anus as I pushed. It was a little easier entering her this time as I popped in a little easier. As it occurred the night before, as soon as I entered her Denise had an orgasm. After her tremors ceased she whispered, "My god that feels so good!"

I whispered back, "I have never seen anybody cum that quick before!"

Denise began pushing back against me so I began sinking into her depths. She was moaning and groaning constantly as we slowly joined together. When I was all the way in she whispered, "Fuck my ass nice and slow and deep, Tony."

I began pulling most of the way out of her before slowly pushing back in. She felt incredible as I slowly fucked in and out of her. I reached around and grabbed one of her tits and squeezed it hard which caused her to groan with delight. Denise kept muttering as we continued our quiet ass fuck and she had either multiple orgasms or one constant one, I couldn't tell. The constant pulsing of her rectum as she orgasmed began to takes its toll on me. "I'm going to cum!" I whispered to Denise.

"Cum in my mouth, okay?" she said.

"Okay, but hurry!"

I pulled out of Denise's ass and laid on my back as Denise turned around, moved her head towards my groin and then took me all of the way into her mouth. I immediately let loose as my sperm rocketed into Denise's gullet. She sucked and sucked as I moaned. When she was convinced I was done she crawled up my body and kissed me. She then laid her head on my chest as we enjoyed the afterglow of our union. I suggested, after a while, that we take a shower before the other two got up. When we had finished our shower and walked back into the bedroom we could see that Jane and Debbie were awake.

"Good morning you two!" I said. I walked over to Jane and gave her a kiss. "By the way Jane, you have created a monster!"

Jane looked at me, obviously confused. "What monster?" she asked.

I pointed at Denise and said "She wanted me in her ass again as soon as we woke up!" I then started laughing because Denise had a very sheepish grin on her face.

Jane rushed over to Denise and pulled her into a hug and kissed her deeply, "You can have Tony in your ass anytime you want!" They both laughed as did Debbie and I.

"Why don't you and Debbie get dressed so we can eat breakfast! I'm starving! You three need to keep me fed if I'm to perform all of these miracles!"

Jane laughed and said, "Fine, but I want to take a quick shower."

Debbie and Jane took a quick shower, dressed and were ready to go very quickly. As we ate we were debating what we should do during the day. "I don't know if any of you looked outside, but it's raining and pretty hard, too." I interjected. After breakfast, we walked out to the entryway of the lodge to see how bad it really was. Not only was it raining but it was pretty cold as well. We all stood and looked at each other. "We could go out and drive around but we won't see much. Neither Jane nor I brought any rain gear or cool weather clothes. How about you two?" I asked.

Debbie shook her head and said, "Neither did we. We should just stay in all day probably. Too bad we're leaving tomorrow."

Jane clapped her hands and said, "Oh boy! Indoor fun it is! Shall we go upstairs and get naked?"

Debbie and Denise laughed and I just shook my head. As soon as we got in the door Jane had her clothes off quickly followed by Debbie and Denise. Since there was no way to avoid it I pulled mine off too. Jane walked over, hugged me tight and kissed me deeply.

Debbie cleared her throat and then in a tentative voice asked, "Tony, can I have anal sex with you, if it isn't asking too much?"

I smiled at her and replied, "I would be honored to have anal sex with you, Debbie. Jane will get you ready."

Jane smiled and told Debbie and Denise to accompany her in the bathroom once again. They marched in there leaving the door open again so I could listen to what was going on. I got onto the bed, laid back, closed my eyes and thought about all of the sex I had had over the past three days. Jane lived up to her promise after the Astrid weekend of taking some of the 'load' off me in terms of couplings having only had each girl a few times. I was totally wiped out like the Astrid weekend but I still had to get through this day. I smiled to myself thinking that I was doing stuff with three gorgeous women that any other guy in the world would give his left arm to do. I had no reason to complain.

After twenty, or so, minutes, the three women returned to the bedroom. As I watched the three beautiful naked women walk towards me with boobs jiggling and shaved vulvas swollen with lust I couldn't help but get hard. Jane announced that we would replicate Denise's anal introduction. Jane laid down on the bed with her head at the edge, Debbie got on her hands and knees above her and Denise got on her knees and began licking Debbie's anus. I stood and walked behind Denise and watched as she and Jane ravaged Debbie's holes with their tongues. Debbie was moaning constantly as she tried to force each tongue deeper inside of her. At long last Denise pulled back and began slathering KY in and out of Debbie's asshole. She managed to push three fingers into Debbie when she declared that she thought that Debbie was ready.

I moved close to Denise and let her apply the KY to my erection. When she had finished, Denise stood up gave me a quick kiss and said, "Make it as good for her as you did for me." I smiled and then looked down at Jane whose eyes were looking up at me. I bent down and gave her a kiss on her forehead and then positioned myself at Debbie's anal opening. I began to slowly push into Debbie's tight backdoor and when I just popped into her with my head she let out a painful grunt.

"Are you okay? I can stop if you need me to." I said.

With a grimace on her face, Debbie said, "No, don't stop. It hurt a bit initially but it's getting better. You can push a bit more in, if you want."

I pushed a couple of centimeters in and stopped and kept this up until I was ¾ of the way inside her. I asked how she was doing and she replied, "I'm getting used to you while Jane is driving me wild with her tongue!"

Deciding that she was doing okay if she could joke I pulled a little way out and then pushed back in a little deeper. Debbie moaned in a good way so I continued pulling back a little and pushing in further. After several times of this I managed to get all of the way inside Debbie's ass.

'I'm all the way in, do you need me to hold still?" I asked

Debbie, with a husky voice said, "DON'T STOP! FUCK MY ASS, TONY! FUCK MY ASS!"

With those instructions, I began sawing in and out of Debbie with a nice easy tempo. I reached around her and pinched her nipples hard causing her to groan passionately. "MY GOD, DENISE! YOU WERE RIGHT! THIS IS HEAVENLY! FUCK ME HARDER, TONY! FUCK ME HARDER!" Apparently, Debbie was enjoying herself so I began pounding into her as hard as I could. With each time I hit her butt with my pelvis she would cry out "YES". Debbie then startled me by asking to be spanked! I wasn't accustomed to hitting people and it must have showed as Denise walked up next to me.

Denise swatted Debbie hard on her right ass cheek with her open palm. Debbie let out a deep groan as soon as Denise slapped her. "When Debbie gets really turned on she likes to be spanked. She says it accentuates the experience! I can do it for you!" And with that Denise gave Debbie's ass several hard slaps. Each time Debbie groaned with desire, her cheeks were bright red from the spanks she received and I kept pounding into her as I felt my climax rising

All of a sudden Debbie cried out that she was cumming. I could feel her shake and shiver and her rectum squeeze me. I wasn't quite there yet so I kept pounding into her ass. Debbie cried out, "AGAIN! I'M CUMMING AGAIN!" and I continued hammering away.

Finally, my own release was at hand as I let out a primeval grunt and shot my load into Debbie's colon. My penis spasmed for quite a while before it finally stopped. Jane was sliding out from under Debbie as I pulled out of her. As soon as I was clear Denise knelt behind Debbie and began sucking the sperm from her ass. Debbie collapsed face first onto the bed and Denise followed he down as she kept tonguing her abuse anus.

Jane walked over to me, threw her arms around my neck and pulled me into a deep passionate kiss. "Do you have any conception of how much I love you?" she asked as she broke the kiss.

"I do, it is slightly less than how much I love you!" I replied.

"Ooh, that was a good answer. How long have you been saving that one?" Jane asked with a twinkle in her eye.

"I made it up just now, if you want to know!"

"The love of my life has a quick wit! I got the whole package with you!"

"Indeed you did. I'm exhausted and it isn't even lunchtime! Would you mind lying down with me for a while?"

"I would love to."

We went to the other bed and I laid on it in the middle. I expected Jane to lie in front of me but she was behind me. I felt her warm body on my back and butt and it felt very nice. I could feel her breasts squeeze up against me and my ass nestled into her pelvic area. With her arm around my chest she held me tight. It felt so good I fell asleep fairly soon.

When I awoke, Jane was still up against my back so I turned to face her. She whispered, "Debbie and Denise are asleep. We should let them. Did you sleep well?"

I whispered back, "I did. It felt really nice to have you behind me. I liked it."

"I thought you might. I love it when you are behind me holding me tight. It is one of my favorite things you do for me. It makes me feel content, safe and loved all at once. I thought I would return the favor."

I leaned in and kissed Jane with all of the passion I had. We laid there for quite a while just holding each other and kissing until we heard the others begin to stir. Jane asked, "Did you two sleep well?"

Denise sat up and said, "Yeah, it was very nice. You?"

"Yep, it was great. Why don't you guys come over here and lie down with us so we don't have to shout across the room." Jane asked. Denise and Debbie crossed over to our bed with Denise getting in front me and Debbie behind Jane. Jane continued, "So Debbie, how was your first anal experience?"

"It was a little rough at first but got better quickly. Thank you, Tony for being such a great lover. You were perfection. I hope I didn't freak you out with the spanking request?"

I chuckled and said, "I have to admit I was a little taken aback. I'm not sure if I could hit somebody."

Debbie replied, "Don't think of it as hitting. Think of it as enhancing your partner's experience. As long as the spanking isn't intended to cause harm and is requested by your partner it's a good thing. It really gets me going and makes my orgasms twice as good. I have never cum as hard as I did with you just now and the spanking was the icing on the cake."

Jane said, "I think I would like to be spanked sometime."

I laughed and said, "Now there's a surprise!"

Jane laughed and said, "Yeah I know, you're probably right! I do tend to like everything. But, I have recently fantasized about getting spanked really good so my ass cheeks are crimson red and then you fuck my ass as hard as you possibly can with my cheeks burning. I'm getting wet just thinking about it!"

"Really?" I asked.

"Yeah, I'm soaking wet down there. Do you want to make my fantasy a reality?"

"Oh, wow. I don't know. I don't want to hurt you."