Year Two with Jane and Tony Ch. 02

Knowing sleep was going to be postponed for a while, I asked, "What does the beautiful girl have in mind?"

"Nothing really. You're tired, so you should sleep. We can make love another time," Cindy said.

I was taken aback and said, "Really? I would like to sleep. I'll make it up to you, I promise."

Cindy smiled as she lay next to me. She kissed me, nestled her head on my chest and said, "Good night, sweet prince..."

Jane looked at us both, then turned off the light and settled down on my other side. Before long I was sound asleep.

When I awoke in the morning, I had to slide off the end of the bed in order not to disturb Jane and Cindy. I went into the kitchen, made coffee and then took my cup of coffee out onto the lanai. I had my tablet and scanned the headlines while waiting for everyone to wake up. As I finished my cup of coffee, Jane walked out all bleary eyed and gave me a kiss. I got up and walked back into the kitchen with her to fetch another cup of coffee.

Jane asked, "What should we do today?"

"I'd like to go snorkeling like we did last year," I replied.

"We don't have enough gear for everyone to go at the same time," Jane said. "Perhaps you can nip into town and buy a couple more sets of fins, masks and snorkels."

"Okay," I replied. "I'll take Sofia with me, she's fun to shop with."

When everyone finally got up we had breakfast and then Sofia and I drove into town to get additional snorkeling equipment. Sofia saw a shop that sold swimsuits and decided she wanted to check it out. I told her she really didn't need one but she said she wanted something for when she was with Blair. She looked through several racks but didn't find what she was looking for. Finally, a clerk asked if she could help and Sofia said, "Yeah, I'm looking for something that will give a friend of mine an instant erection!"

The clerk said, "Oh, those are back here. Your size should be in amongst these." Sofia and the clerk, both looked through the rack until the clerk pulled out a mass of red string. "I think you would look wonderful in this one. Why don't you try it on?"

Sofia looked at the garment, smiled and said, "Yeah! That looks like what I want." Sofia was lead into a changing room and after a few minutes she called me to come see. I went back towards where Sofia had changed and when I looked into the room I gasped when I saw her. The bra was made up of two very small triangles of very thin material about an inch wide and 4" tall, barely covering Sofia's nipples. The material was so thin I could make out her piercings quite clearly. The bottom was, basically, red string with an inch-wide strip at her vulva that allowed her labia to be exposed. Again, the material was thin enough so that I could clearly make out her piercing. All in all, the suit had its desired effect because I got hard instantly.

At about this time the clerk walked back to see how Sofia was doing. When she saw Sofia, the clerk smiled and said, "Not only has it made your friend get an instant erection, but it has made me instantly wet! That looks really hot on you!" Sofia smiled and said, "I'll take it. We're here with 3 other girls that I think will want to check this place out. We'll probably be back!"

As Sofia and I drove back I asked, "You said that suit was for a friend, I trust you were referring to Blair?" Sofia affirmed that she was. "You didn't call him your boyfriend. Anything in that?"

Sofia sat quietly for a moment and then replied, "Yeah, I'm not too sure how much longer we will be hanging out. He has been, kind of, weird about my relationship with you, Jane and the others. He's been trying to get me to move back into the dorms. The problem is that I love you, Jane and the others more than I like him. Actually, I'm starting to like Evan a lot more than I like Blair. Blair has been, sort of, manipulative lately. I'm getting pretty tired of it. He threatened to tell his father about our lifestyle and I told him that if he did that I would kick the holy shit out of him and accuse him of attempted sexual assault! I, kind of, scare him...a lot!"

I laughed and said, "You don't want to make false accusations about anyone. I don't have a problem if he tells anyone how we live. Dr. Prescott is a pretty reasonable man. Do you think your breaking things off with Blair will affect Evan and Cindy?"

"Evan and Cindy aren't an item, they're just fucking buddies," Sofia said. "I don't know, things just got too complicated. Why can't everyman be like you? You know I love you, don't you?"

"I know you do and I love you as well," I said. I then pulled off the road and pulled Sofia into a hug. She cried on my shoulder for a few minutes while I held her and stroked her hair. After a little while Sofia stopped crying and looked into my eyes. I wiped the tears from her cheeks and kissed her on her nose.

"Thanks for that," Sofia said. "I can't remember the last time I cried. It felt, kind of, good. Let's get back and go snorkeling!"

As we started driving again, Sofia returned to her usual self. When we got back to the house, Sofia modeled her new swimsuit for the others. They all went wild and said they had to check out the shop sometime. After a while we all headed down to the beach to snorkel. The tide was up which caused us to walk a little way before we hit the deeper water. I was, again, astonished by the amount of sea life under the water. The colors and varieties of fish were astounding as we swam in our little harbor. We all swam together in a group and we each pointed out things of interest that we saw.

After about 45 minutes we all headed back to the beach. We had brought a cooler with bottles of soft drinks, a bunch of beach towels and a couple of big umbrellas for us fair skinned ones. Jane, Sofia and Cindy worked on their tans while Sue and I sat under the umbrellas. There was a nice breeze blowing in off the water while the sound of the waves breaking lulled me to sleep.

After a while I was awakened by the sound of laughing. I sat up and asked, "What's so funny?"

Jane looked at me and said, "I was recounting what we did on this beach last year. If you'll remember, you fisted both my pussy and ass at the same time one day and then fucked my ass when I had a pop bottle in my pussy on another!"

I laughed and said, "And the smell of coconut oil still make me hard!"

Cindy grabbed her pop bottle and quickly swallowed the contents and then after quite a loud burb asked, "Will you do the pop bottle DP on me?"

Jane told Cindy to get on her hands and knees then took Cindy's bottle from her. Jane then poured some of the tanning oil down Cindy's ass crack and smeared some of the oil on the bottle before working it into Cindy's vagina. Soon, Jane was fucking Cindy good and hard with the bottle and then put a couple of fingers into Cindy's ass. When Jane figured that Cindy was ready, she called me over. Jane removed her fingers from Cindy's ass, oiled my cock up and then placed me at Cindy's anus.

I slowly pushed into Cindy's rosebud slowly, amazed at how tight she was with the bottle in her. It took me some time to penetrate all of the way into her. All the while Cindy was crying out. "OH FUCK! YES! YES! YES!" Cindy then turned her head to look at me and said, "FUCK ME HARD TONY! THIS HURTS SO FUCKING GOOD!" I didn't want to injure the girl so I fucked her at a moderate tempo until she cried out, "FUCK ME HARDER! POUND MY ASS!" I decided that Cindy knew what she wanted so I began pounding into her with everything I had.

I noticed some movement to my left and when I looked over I saw Sofia working a fist in and out of Jane's ass while she was working her other fist into Jane's pussy. It was quite a sight as I continued to pummel Cindy's backdoor. A couple of moments later, Sue crawled up to me and kissed me deeply while she reached around and played with Cindy's breast. When Sue broke the kiss, she looked into my eyes and asked, "Will you fuck my ass some day? I think I would really like that!" I told her I would love too and then she began kissing me again with even more passion.

Before long I could feel my climax building and cried out, "I'M GOING TO CUM! SUE, PULL ON CINDY'S CLITORIS PIERCING!" Sue bent down and felt for Cindy's piercing and before long Cindy let out a piercing scream as she had a monster orgasm. My orgasm peaked moments later as I flooded Cindy's rectum with my cream. When I had finished pulsating I pulled out of Cindy's bum only to watch Sue dive in to lick the spunk from her ass. Sue was also pulling and pushing the bottle while she continued to pull on Cindy's 'triangle'. This caused Cindy to have nearly constant orgasms until she collapsed onto her belly a twitching mass of humanity.

I looked up just in time to see Jane have a massive orgasm, literally, at the hands of Sofia! Sofia kept up the fisting as Jane continued to climax. Finally, Jane could take no more and collapsed on her towel. Sofia pulled her hands from Jane's orifices and sat there with a grin on her face. I pulled the bottle from Cindy's vagina as Cindy turned over onto her back. "Tony, that was awesome," Cindy rasped. "I came so hard I couldn't believe it! Sue and Sofia, you guys have to try that!"

I laughed and said, "Nobody is trying anything with me for a while. You used me up Cindy! Do you guys want to stay down here or go back up to the house?"

Everyone seemed to have had enough sun and surf for the day, so we packed up our stuff and wandered back up to the house. When we had stowed the gear away I jumped into the swimming pool to cool off. Sue jumped in as well and swam over to me and asked, "Do you think you would be able to have butt sex with me tonight?"

I replied, "Yes, I should be adequately recuperated by then. Are we partners on the bed schedule tonight?"

"Yes, you and I share the guest room tonight," Sue replied. "Do I need to do anything special?"

"Let me talk to Jane and tell her what you want to do," I said. "She will help you get ready when the time comes. Are you sure you want to do this?"

"I am! I really like fingers in there and Sofia and Cindy always talk about how great it is. They also told me you were their first and that you were really gentle and caring. Are you okay with doing it with me?"

"I'm fine, I just want to make sure that this is something you want. I just want you to know it might hurt and that it is alright to say stop at any time. Okay?"

"I understand," Sue replied. "I think it will be alright, especially with you." Sue smiled and then hugged me. "I just want to say thank you, for allowing me to join you on this holiday. You and Jane are the kindest and most generous people I have ever met. I now understand why Sofia, Cindy and Barb love you so much. I'm pretty sure I love you too!"

"Well, I love you as well as does Jane. We're very happy to have you along with us on our holiday," I replied. After a few moments I said, "I'm getting, kind of, hungry, how about you?"

Sue smiled and nodded her head. We got out of the pool, dried ourselves off while I announced to Jane that it was lunchtime! Sofia and Cindy were in the pool so Jane, Sue and I went into the kitchen to make lunch. While we were putting together sandwiches I told Jane about Sue's desire to have anal sex tonight. Jane smiled at the redhead and said, "I'll show you how to get ready, just before we go to bed tonight. Would you like me to be with you during?"

Sue thought for a moment and said, "I think I will be fine. You don't mind, do you? I mean, Tony is your husband and everything."

Jane pulled Sue into a hug and said, "I don't mind in the least. We love you."

The rest of the day was pretty quiet as we all lay about reading and talking. After dinner, I could see Sue was getting a bit jittery so, I sat next to her and asked her if she was alright. "I'm fine, just a little anxious about tonight," she replied. "I'm not scared, I'm really looking forward to it because I'm very horny!"

"I'm relieved," I said. "I thought you might be getting cold feet but, was afraid to say anything. I just want to reiterate that you can say stop at any time. There is no pressure to do anything, okay?"

"I understand," Sue said. "I really want this. I'm pretty sure it's going to be the best sex I have ever had!"

After a while, Jane came and sat with us and asked Sue, "Are you ready?" Sue nodded and then both women stood and walked back towards the bedrooms. I took that as my cue to get ready for bed. I brushed my teeth and then retired into the guest bedroom. A short while later Sue entered the room and walked over to the bed. She was radiant in her excitement and looked very beautiful. Her breasts swayed as she walked and her faced beamed.

As Sue got to the bed she handed me a tube of KY and said, "Jane told me to give this to you to supplement what was in here already. She seemed to think I was going to like anal sex."

This statement piqued my curiosity for a moment and then I pulled her into the bed with me. Sue was shaking slightly, much like the first night we had sex. "Why don't we just start like we did the first night we had sex, okay?" Sue nodded and then lay down at my side. As soon as we began kissing her nerves disappeared. We kissed passionately for many minutes while we ran our hands all over each other's body. We were laying on our sides so, after a while, I pulled Sue's left leg up over my hip. I was now able to reach both her pussy and her anus.

I ran my fingers through Sue's very wet pussy a few times and then ran my fingers to her backdoor, getting it nice and slick with her dew. I then began working my finger around her sphincter for a bit and then began pushing it in slowly. I would run my finger back to her vagina for more of her moisture and then back to her ass until I had her quite well lubed for my fingers. Once I had my index finger into her ass, Sue let out a long low groan of ecstasy. I asked her, "Do you like that?" and she replied in a whisper 'Oh, yes!' I worked my finger in and out for several minutes until I asked her, "Would you like another finger?" Again, Sue whispered, 'Oh yes'.

I got my middle finger wet with Sue's dew and then pushed both fingers into her rosebud slowly. Sue was breathing heavily as I worked my fingers into her rectum and then moaned loudly as I got them both all of the way in. I asked her how she was doing and she said, "I'm in heaven!" With that I began stroking in and out of her with my fingers. I, also, added my ring finger to Sue's pussy, getting it ready to add to the other two. Before long Sue asked me to add the third finger to her ass. Once I got it in and was stroking her she began kissing me again very passionately, groaning and moaning the whole time.

Finally, Sue broke the kiss and said, "Will you make love to my bottom now?"

"How would you like to do it," I asked? I can get behind you, doggy style, you can lay on your back with your legs pulled back or you can be on top."

"Take me from behind, first," she replied.

I pulled my fingers out of her backside and then got up on my knees as Sue got onto her hands and knees. I grabbed the tube of lube that Sue had brought with her and removed the top. But, before I applied it I bent down to lick her rosebud for a while causing Sue to moan once again. "That feels wonderful, I love it," she muttered! I licked her on, in and around her anus for several minutes until she asked me to make love to her bottom once again. I applied a generous amount of the gel to her pucker and worked it into her really well and then applied a large amount to my penis. I then positioned myself at her opening and began pushing in. The going was slow as Sue was very tight. I paused for a second once I breached her sphincter but, Sue kept pushing back on me as she muttered and moaned. Before I knew it, I was totally ensconced in Sue's ass! "Oh my god! Oh, my god," Sue rasped out!

"Are you okay," I asked? "Should I stop?"

"Please don't stop! Please fuck me now!"

I slowly pulled back and then pushed back in slowly. Sue was moaning constantly. Again, I pulled back slowly a little farther this time and then pushed back in. Sue was so warm and tight I wasn't sure how long I could last. I pulled back further until just the tip of my cock was inside Sue and then pushed back in slowly. "Ooh! Just like that," Sue whispered. I was a little surprised by how quiet Sue was. I was so used to Jane being so demonstrative while in the throes of passion that I was afraid that Sue wasn't enjoying herself. However, my fears were allayed when Sue announced, "Oh my god, I'm cumming!"

Sue was shaking quite hard which caused me to pull out of her by accident. I quickly grabbed myself and reinserted my dick in her ass, plunging all of the way in. Sue said raptly, "Do that again! That was nice!" I pulled all of the way out and then plunged back into her ass to the hilt. "Oh yes! Again!" We did this for several minutes until she asked me to resume fucking her. I continued with the long strokes but picked up the pace a bit. Sue had another orgasm and then asked me to pinch her nipples. I reached around her and pinched her nipples, rolling them between my thumb and fingers.

Pretty soon I felt my climax rising so told Sue I was going to cum soon. She told me she wanted to feel me cum in her ass so I continued thrusting into her until my orgasm hit. "I can feel you pulsing inside of me," Sue said. I made to pull out of her but she asked me to stay inside her as we lay down on our sides. She turned her head towards me and said, "That was incredible! I must have climaxed 10 times and I never touched myself," Sue reported.

"Really," I asked?

"Oh yes," Sue replied.

"I was getting concerned because you were so quiet," I said. "Jane, Denise, Sofia and the rest of them scream loudly while they have anal sex. I was afraid you weren't enjoying yourself."

Sue chuckled and said, "Oh, I was enjoying myself! That was the best sex I have ever had. I want to do it again as soon as you're ready. This time I want you to fuck me really hard like you did with Cindy this afternoon!"

I said, "Since I have come twice today, it may be long and arduous before I cum again. Are you sure you are up for that?"

"Oh god, yes," she said! "The longer and harder the better I think!"

I was still inside of her bum and I could feel her squeeze and release me and push back on me as we talked. I got up on my elbow so that I could lean over and kiss her. She put a hand at the back of my head and pulled me in for a hard, passionate kiss. I, also, reached around her and began playing with her nipples. Before long I began getting hard again as Sue continued to work me in and out of her rectum. When I was good and hard again, Sue asked, "Will you fuck me from behind again? Fuck me hard? Make me scream? I want it to feel frenetic, like there's nothing existing in the world but my ass and your penis. Can you do that for me?"

"I can try," I said. "Get on your hands and knees."

Sue got on her hands and knees and then bent over and spread her ass cheeks very wide. "Just plow into my ass. Show me no mercy. Pull my hair, slap my tits and ass! I want to feel everything!"

I knew what she wanted. Jane and Barb would get this way on occasion. I used to find it difficult to do because I didn't want to hurt them but they said the hurt is what made it good. I still found it hard to come to grips with that but, I also wanted them to have whatever they wanted. I kneeled behind Sue, lined my cock up with her widespread asshole and just jammed it home. Sue's only reaction was to grunt and utter 'yes'. I grabbed her hips and began pounding away as hard as I could. Sue released her cheeks and pushed her body up so that her breasts were swaying with my thrusts. I reached around with my right hand and grabbed her right breast hard, squeezing it like I was squeezing a lemon. I then released her breast and pinched and pulled her nipple as hard as I could. Again, Sue's only reaction was to moan, 'yes'. I grabbed her left tit and did the same thing while I was pumping into her backdoor.