Another Chance

"Good morning beautiful!" I said to Jan.

Jan smiled brightly and said, "Good morning handsome!"

I leaned in and kissed her lightly and then she got up and headed for the bathroom. I admired her lovely ass as she walked towards the bathroom and began remembering today's possibilities. When Jan returned to the bed she yanked the covers off of me to expose my hard-on, smiled and then crawled up my body until she was straddling it. She took me in her hand and began working me into her wet pussy.

"I was dreaming all last night about doing this very thing! It's so nice to make a dream come true!" Jan laughed.

"Well, I'm happy to oblige. Oh, my...that feels so good!" The feeling of Jan slowly lowering herself on my manhood was exquisite. I reached up and took each of her breasts in my hands feeling their weight and squeezing each one.

"I like my nipples to be pinched hard and pulled," Jan panted. "Oh fuck, Jimmy. I love how you feel in me!"

Once Jan had me all of the way inside her she began lifting and lowering herself very slowly. I could see her tremble every now and again as she slowly fucked me. After a while she bent over to kiss me deeply and passionately and then she straightened up again. She was getting quite wet because I could feel her moisture running down to my scrotum and dampening my pubic hair. Everything was so sensuous as we continued our slow mating. After 15 minutes, I began to feel my orgasm begin to rise up and told Jan I was going to cum real soon. She smiled and said, "Me too!"

After a couple of more minutes my climax was on me and I groaned as my seed blasted its way into Jan's womb. Jan wasn't very far behind me as she too climaxed. We held each other tightly as we spasmed and convulsed our way through our orgasms. When finished, we laid together with Jan on top of me, both of us a sweaty mass of happy humanity.

When we had both calmed down Jan said, "That was fantastic! Thank you!"

I laughed and said, "You did all of the work, thank you!"

We both laughed for a bit and then I said, "Look, why don't we take a shower, get dressed and wander over to my place where I'll make you a wonderful breakfast! Besides, it will give the hotel staff a chance to change the bedding!"

"That sounds wonderful! I'm starving!"

We both jumped up and hit the shower and once again scrubbed each other thoroughly. We then got dressed, me in what I had on the night before and Jan in some light shorts and a light blouse sans undergarments. She gave me a wicked smile as she dressed and I had to resist the temptation to ravage her again. We walked hand in hand to my condo which was only a few blocks away.

"I love your place. It reflects you really well. Wow, what a great view!" Jan said.

I took her hand and led her out to the balcony and pointed out some of the various mountains that were visible on such a clear day. I then said, "I have two questions for you. One, what would you like for breakfast? And, two, what kind of music do you like?"

Jane pondered for a moment and then replied, "I'm up for anything for breakfast so surprise me. Second, you'll probably laugh at my musical taste but I like to listen to classical music."

My smile couldn't have been any bigger as I said, "Classical is my favorite too! How about some Mozart piano sonatas?"

"I just adore Mozart!" Jan said. "Wait a minute...did you call a friend of mine to find this out?"

I laughed and said, "Nope! Take a look at my CD collection!"

I turned on the music and then headed to the kitchen while Jan inspected my collection. I decided to make French toast and cut up a bowl of fresh fruit. After a while Jan wandered in and offered to help but I told her I had everything under control and that she should sit at the breakfast bar and talk to me.

"Do you remember the music teacher in school, that bald guy who's name I've forgotten?" Jan asked.

"Yeah, he sucked! I wanted to learn how to play the saxophone but he just ignored me because there were a couple of girls who had had lessons before. I got nowhere with it so I dropped it. I never forgave the prick!"

"Well, he got fired from what I had heard. He used to touch us girls, especially the ones who had breasts, inappropriately. He would brush up against us with his arm as he would point something out on the sheet music. Do you remember Lillian whose father was the bank president?"

"Yeah, uh, Lillian Metzger, I think. She had some big, well, you know..."

Jan chuckled and then carried on, "Yeah, her. She mentioned that the teacher was doing it to her all of the time to her Dad and her Dad was none too happy. There was an investigation and he got fired and was damn near thrown into prison!"

"How did you hear all of this?" I asked.

"Oh, I stayed in touch with Rita for several years."

I finished up making our breakfast and told Jan we could eat out on the balcony if she would like. She said that would be nice so we hauled our food and coffee to the balcony. We ate and reminisced about our old days in junior high. When we finished, Jan helped me with the dishes and tidy things up. When the clean-up was done, I asked Jan what she would like to do.

"Would you mind just walking around downtown, maybe do a little window shopping and then going to one of those food carts for lunch?"

"That would be fine with me. There's a nice pod of food carts quite near here. We could bring the food up here to eat and then, maybe, I can make dinner for you here. Sound good?"

"That sounds wonderful. If you knew how many hotel rooms I've stayed in over the years you would understand my glee of escaping them!"

"In that case, why don't you just stay here with me for the rest of your stay. I would really love to have you."

Jan smiled and said, "I would love that too. If I check out now the company won't be charged for the extra nights."

We quickly made our way back to the hotel where she told the front desk of her change of plans. They had no problem with the change so we ran upstairs to collect Jan's belongings while the desk figured out her bill. When we returned to the desk Jan gave them her corporate credit card, paid the bill and off we went. We returned to my condo and put Jan's bag in the bedroom and then headed back out for our stroll around town. I pointed out some of the places of historical significance, took her to the main branch of the library and walked down to the riverfront. After several hours, we decided to hit the food carts for lunch. Jan chose a Thai cart while I chose an Indian cart. The food smelled wonderful as we carried it up to my place.

We dined again out on the balcony and enjoyed the beautiful day. Jan caught me staring at her and asked if I had something on my mind. I blushed and told her I was just admiring her beauty and thinking how lucky I was to be sitting here with her. She then blushed at my statement. We talked a little more until Jan stood and undid the buttons on her blouse and dropped it to the floor. She then undid her shorts and let them drop also, standing naked before me. I got an instant erection as I sat and stared at her beautiful body. I then stood up and took her into my arms and kissed her.

"Would you make love to me here, right now?"

I began peeling my clothes off as Jan leaned on the railing of the balcony. Each balcony had partitions on each side to keep some privacy so I wasn't over concerned with my neighbors. People in some other buildings may have been able to see us but I really didn't care. I stepped behind Jan and ran my hands up and down her back, around the globes of her ass, over her stomach and to her breasts. She felt and looked amazing. I kneeled down and licked her exposed vagina while rubbing my hands around her ass cheeks.

After a few minutes Jan said, "Jimmy, will you lick my anus again?"

I spread her cheeks and began licking from her vaginal opening to her tail bone. I did this a few times before I zeroed in on her little pucker. Like everything else about Jan her asshole was perfect. It was very pink with radial lines reaching outward to her sphincter muscle. As I touched it with my tongue it would twitch a bit. After licking around the rim, I began probing into her with my tongue.

"Oh, Jimmy! That feels so nice! I like it when you push your tongue into me!" Jan cooed.

I continued using my tongue on her until my tongue began to tire. I had pushed a middle finger into Jan's sopping pussy, got it nice and wet and then brought it up to her anus and replaced my tongue with my finger.

"Oh, my! Oh, Jimmy that's really nice! Push it in deeper!"

I worked my finger into Jan's rectum slowly not believing how hot and tight it was. When I got it all of the way in I began sawing it in and out of her slowly. Jan then asked me to fuck her pussy, so I lined myself up and pushed into her slowly. My hand that had the finger in her ass was at an awkward angle, so I pulled my finger out of her, spit on her anus, slobbered on my thumb and pressed that into her.

"OH FUCK, JIMMY! FUCK ME HARD!" Jane cried.

I began pounding into Jan's pussy while driving my thumb in and out of her asshole. It was so erotic having sex on my balcony where anyone could see us I think we both were driven by the sensation. I felt my orgasm welling up in me and before long I cried out that I was going to cum soon. Jan was getting close too. She had reached under herself with on hand to work on her clitoris while I was pounding her from behind. Out of the blue Jan growled with her own orgasm and began quaking as I held her hips. My own wasn't far behind and I shoved myself as deeply into Jan as I could as I released my spunk into her depths. My knees were a bit shaky from the intensity of it all so I pulled Jan back with me as I sat in a chair. Jan was on my lap with my cock still buried deep within her pussy.

After a while Jan stood and then pulled me to my feet. She then took my hand and pulled me into the bedroom where we both collapsed onto the bed. We laid there spooning for a while before either of us spoke. I was enjoying running my hands up and down the side of Jan's body from the sides of her breast to the top of her leg.

Jan broke the silence when she said, "Jimmy, that was amazing...again! I kind of got off on having sex so publically. When you stuck your finger in my ass I thought I would explode. We may have to try anal sex before the weekend is over. I think I'm going to like it! Do you think you would like to try it?"

"Yeah, I think I would like to try it! I'm getting hard just thinking about it!" Sure enough, my penis was raising its head in anticipation.

"We will need some things from the drugstore before we can try it. Maybe we can get the stuff this evening?"

I told Jan it wouldn't be a problem. We fell asleep as we laid there and must have been out for a couple of hours. When we awoke, it was just getting dark. I asked Jan if she was hungry but she said she wasn't. She then said that we should go to the drug store before it closed so we could get the stuff we needed for our anal experiment.

Jan said that she had been interested in trying anal for a while and had researched how to go about it. The results from her research revealed three things, lots of lube, cleanliness inside and out and lots of lube! We walked to a large chain drugstore that was a few blocks away and picked up a large tube of KY, a hot water bottle/enema pack and, just in case we decided we liked it a lot, another large tube of lube! As we walked arm in arm back to the condo I told Jan that we needed to stop in the grocery store for a moment. I directed her towards the wine aisle and bought two bottles of chilled Veuve Cliquot.

When we finally got back to my condo Jan decided that tonight was the night and she headed straight for the bathroom. I put one of the bottles of champagne on ice and brought it and a couple of glasses into the bedroom. I stripped my clothes off, climbed onto the bed and checked my email on my phone while waiting for Jan. I heard the toilet flush a few times and then the shower came on. Finally, after about 30 minutes Jan walked out of the bathroom fully naked. Just looking at her caused my dick to harden rapidly. I stood up, popped the cork on the champagne, poured us each a glass and handed one to Jan.

Jan held her glass up in a toast and said, "Here's to us! It's never too late to find love!"

I touched my glass to hers and said, "To us and love!"

We stood looking at each other as we sipped some of the wine. Jane raised her eye brows as she drank and then said, "My goodness, this is really good when did you discover it? How did you discover it?"

"One of the perks of my job is that, not only do I get to fly to places like Europe for cheap, I also get to fly in first class and business class if there are seats available. They used to serve this in business class 10 years ago and I found it was my favorite. I even went to their cellar in Reims, France to take a tour! Drink up!"

We walked around the condo drinking our wine and ended up standing out on the balcony looking at the city lights. Jan looked beautiful naked, bathed in the dull light of the night. When we had finished the bottle of champagne she took my erection in her hand and pulled me back to the bedroom. We stood and kissed for several minutes until Jan said, "Make love to me Jimmy."

We climbed onto the bed and laid together kissing, hugging and fondling one another. When I touched her vagina, I found it to be soaking wet. I inched my way down her body with the goal of drinking her wetness in and did so when I arrived. Her nectar was wonderful as I lapped at her slit and then worked my way up to her clit. After several minutes Jan had her first orgasm of the night. When she had calmed down I told her to roll over for me. Jan did as I asked and then lifted her lovely derriere into the air for me.

I dove into the crack of her ass and lapped at her rosebud tasting the juice of her pussy that had leaked down. I licked her like a man possessed knowing that soon I would be able to sink my penis into her delectable hole. After several minutes Jan groaned and told me to put a finger in her. She reached under a pillow and grabbed one of the KY tubes she had stashed there and handed it back to me. I took off the top and squeezed some onto my finger and then gently rubbed it around her little muscle. I squeezed a little more on my finger and began pushing into her tightness very slowly. Her anus yielded to the pressure and my finger slowly sank into her rectum aided by the slickness of the lube. I pushed into her in small increments allowing her body to adjust.

Once I had my finger all of the way in, I asked, "Are you okay? How does it feel?"

"I'm fine and it feels really good, work your finger in and out now." Jane whispered.

I began to slowly fuck Jan's anus with my middle finger. I was beginning to wonder how my penis was going to fit because of the tightness my finger was experiencing. After several minutes Jan asked for a second finger. I pulled the first one out and lubed up my index and middle finger and then pressed them into Jan. As I sank my fingers, Jan let out a low moan and said, "This feel wonderful!" I followed the same procedure as I did with one finger and before long I was pushing in and out of her rectum. In an effort to stretch her sphincter a bit I began separating my fingers and twisting them as I pushed and pulled. Jan's moans were constant and when I looked at her face she had a smile on it.

After several minutes of my fingers, Jan said, "I think I'm ready for you cock now, Jimmy. Make beautiful love to my ass!"

With that I pulled my fingers from her butt, lubed up my cock really well, slathered more lube in and around her anus and then placed my dick at her slightly gaping rosebud. I then slowly pushed my rock had cock forward slowly as I watched her anus stretch to accept me. Jan cried out, "OH GOD!" very loudly so I stopped pushing and asked her if she wanted me to stop. "DON'T STOP, JIMMY. IT HURTS A LITTLE BUT IT FEELS REALLY GOOD TOO!" I continued pressing forward and couldn't believe how good Jan's ass felt on my erection. I stopped at intervals, again, to allow Jan time to adjust. Before long I had fully impaled Jan's ass with my cock!

"MY GOD, JAN! I'M ALL OF THE WAY IN YOUR ASS! YOU FEEL SO GOOD, I CAN FEEL EVERYTIME YOU SQUEEZE JUST A LITTLE."

"YOU FEEL SO GOOD IN ME, JIMMY! YOU CAN SLOWLY FUCK ME NOW!"

I almost didn't want to move because it felt so good to be buried in Jan's colon, but move I did. I slowly pulled part way out and then slowly pushed myself back in deep. Jan moaned continually as I slowly fucked her ass. I had never experienced anything like it as the tightness and heat of her bowel was incredible. I reached around and grabbed her right breast and kneaded it gently while I continued to slowly pump in and out of Jan's butt.

Jan began pushing back into me as I thrust forward causing the pace to pick up a little. Jan cried out, "THIS IS SO GOOD! FUCK ME HARDER!" My lust was increasing so I had no problem as I began to fuck Jan's ass harder and harder until I was plowing into her as hard as I could.

I began to feel my orgasm rising up in my loins so I cried out, "I'M GOING TO CUM SOON!"

Jan replied, "ME TOO! FUCK ME, JIMMY! FUCK ME!"

"I'M CUMMING!" I yelled out as my sperm began rocketing out of my cock into Jan's colon! I wanted her to cum too so I continued thrust in and out Jan's anus.

Finally, Jan called out that she was cumming and I buried myself as deep as I could as we both savored our release. It felt like my climax had lasted an hour it was so intense. Jan collapsed on the bed with me on top of her. I didn't want her to feel squashed so I started to roll off of her back.

"Oh, Jimmy! Stay where you are and stay in me. You feel so good!" Jan said.

I remained where I was and enjoyed it when Jan squeezed her rectum on my cock periodically. In due time, though, my penis shrank down to its flaccid state and fell from Jan's anus. I took that as my cue to roll of Jan and laid at her side. We faced each other on our sides and kissed each other lovingly for quite a long time.

Finally, Jan looked at me and asked, "So, did you enjoy our anal adventure?"

I smiled and replied, "Yes! It was the most intensely sensual thing I have ever done. Did you enjoy it?"

"Oh my god, it was incredible! It hurt a little at first but then it just felt amazing! I hope we get to do it again!" Jane replied.

"Do you need anything? Food? Drink?"

"No! All I need is you here next to me," Jan replied and then she kissed me deeply again.

After a while Jan got up to use the bathroom. When she finished, I used it and then returned to bed. I turned off the light and cuddled up to Jan spooning her with my front against her back. I was enjoying the sensations of her naked skin against mine. After twenty minutes or so Jan spoke.

"Jimmy, I hope you don't mind but I think I'm falling in love with you. These last two days have been better than any other time I can remember. You are so kind and sweet. You are a terrific lover and I just want to be with you all of the time. Do you mind?"

I hugged Jan's body to mine and replied, "I don't mind in the least because I know I'm in love with you. When I saw you in the airport, all of my old feelings towards you came rushing back in a tsunami! Remember when we were in school and we gave valentine's day cards to all our classmates? Well, I always picked out the best one for you! I have always loved you and will always love you!"

Jan turned over in bed to face me. I could detect her smile in the faint light of the bedroom as she said, "Really! You love me too? Oh, Jimmy kiss me please!"

I pulled Jan to me and rolled her on top of me and kissed her with all of the passion I had. I had never been in love like this before and I just wanted to sing it out to everyone. After a while she rolled back off me and as we laid on our sides looking at each other Jan said, "Would you like a roommate?"