Another Chance

PUBLIC BETA

Note: You can change font size, font face, and turn on dark mode by clicking the "A" icon tab in the Story Info Box.

You can temporarily switch back to a Classic Literotica® experience during our ongoing public Beta testing. Please consider leaving feedback on issues you experience or suggest improvements.

Click here

I asked, "What do you mean?"

"My meeting on Friday was with a local company that was offering me a job as their VP of sales. I told them I would have to think about it. I think I want to take their job if it means I can live and be with you!"

"That would be wonderful! I would love to have you live with me. I have a bit of a confession to make to you. You see, I really don't need to work. I just do it to fill in the day. I inherited quite a fortune a few years ago from an Uncle who had no kids and who really liked me. Didn't you think it was weird that a customer service person for an airline could afford a nice condo like this? I propose we both quit our jobs, you move in here with me and we spend our lives together blissfully!"

Jan looked at me wide eyed and then said, "Don't you think we would get bored without jobs to go to?"

"Not really," I replied. "I was bored before because I had nobody to share my life with, so I got my airline job to give me something to do. I told myself if I ever found a partner to share my life with I would quit my job and enjoy life. So, what do you think?"

"I think you just found a partner to share your life with!"

When I heard that I pulled Jan to me and kissed her deeply. "You have just made me the happiest person on earth!" I said after we broke the kiss. After a while fatigue set in and so we resumed spooning each other and fell asleep.

I awoke the next morning to the feeling of my penis being stroked. I whispered into Jan's ear, "Good morning! What a wonderful way to wake up!"

Jan turned her head and said, "Oh, just wait, it gets better! I want you in my ass again!"

It turns out that Jan was slathering my cock with KY. She pushed herself back against me as she positioned my penis at her anus and then she pushed back allowing me to penetrate her backdoor. For the second time in as many days I felt the exquisite tightness of Jan's rectum as I slowly sank into her.

"MY GOD THAT FEELS NICE!" Jan called out. When I had penetrated all of the way into her bowel I pulled Jan over on top of me so she was in a reverse cowgirl. She propped herself up and began working me in and out of her ass. After a while Jan sat up onto her knees so she could more easily control the tempo of our anal coitus. I marveled as I watched my cock slide in and out of her as her anus stretched to accommodate my girth. I massaged the globes of Jan's ass as she looked over her shoulder and smiled at me. I just laid back and let Jan control the pace of our lovemaking. I saw Jan move her right hand towards her pussy as she began to let her fingers work on her clitoris. After several minutes Jan cried out that she was going to cum. I told her I wasn't too far behind!

A couple of minutes later Jan let out a low groan as I felt her rectum begin to pulse on me. The sensations were so wonderful that, I too, lost it and began shooting my sperm into her colon with a mighty groan. When I quit spasming I was sure I had died and gone to heaven. Jan kicked her feet out from underneath her and fell back lying on my chest. I reached around her and gently massaged her breasts as we came down from our sexual high. When we had recovered, I said, "Let's shower, eat breakfast and then go furniture shopping. You'll need a dresser of your own amongst other things."

Jan replied, "Actually, I have a dresser and a few other furniture items that I think would fit in nicely here. I will tell you about them while we eat, now let's shower!"

We had a fun shower washing and teasing each other. Afterwards we ate our breakfast and then went to the art museum. Although the museum is kind of small, they do have an impressive collection of several masters. We both said our favorite was a Monet that is the pride of the museum. We walked around town for a while and then headed back to the condo. Jan excused herself and went off to the bedroom while I fixed us a light lunch.

When Jan returned, she snuck up from behind me and grabbed me in a bear hug and kissed my neck. I turned in her arms to discover that she was naked so I pulled her into a kiss and grabbed both cheeks of her delectable ass. When we broke the kiss, she asked, "May we eat out on the balcony again?"

I gave her my best lecherous leer and said, "As soon as I finish dining in the kitchen!" With that, I hoisted Jan up onto the kitchen counter, pushed her legs up so her feet were on the counter, spread her legs wide and dove in, face first, into her delicious muff while stripping my own clothes off! I licked her to the best of my ability drinking down her dewy moisture and teasing her clitoris. "My god, you are scrumptious!" Jan laughed between moans. I licked deep into her vagina for a while before moving down to lick her slightly swollen anus for a bit. I then moved back up and gave her clit a serious thrashing driving her to an orgasm. While Jan cried out in ecstasy, I stood up and then slid my iron hard erection deep into her honeypot.

"OH MY GOD! JIMMY, FUCK ME HARD!" Jane cried out.

I grabbed onto Jan's ass cheeks and began pounding into her with everything I had. After just a couple of minutes Jan cried out that she was cumming again. Jan leaned over and pulled my face towards her and gave me a very passionate kiss while I plowed into her pussy. A few minutes later she leaned back and said she was cumming yet again! I wasn't far behind her now and cried out I was going to cum. Jan shoved me backwards, jumped off the counter and took me into her mouth just as I climaxed. She pulled her head back a bit so I was just outside of her mouth as I continued to shoot numerous ropes of sperm into gaping maw! When the last spasms left just a dribble of my cum escaping the end of my dick, Jan took me back into her mouth and sucked me dry.

When she determined I was done, she pulled back off my cock and announced, "You are scrumptious too!" I laughed, pulled her up off her knees and hugged her tightly. We kissed passionately for several minutes and then took our lunch out to the balcony. It felt kind of liberating to sit naked outside while we dined.

We took our dishes back into the kitchen when we had finished eating and tidied things up a bit. When we had finished, Jan asked, "Can I ask a favor of you?"

"Sure, anything you want."

"Well, when I take you in my mouth your pubic hairs tickle my nose, so I was wondering if I could shave you down there?"

I looked at Jan, a bit surprised, and replied, "Yeah, if you'll let me shave you. I have always wondered what it would be like to eat a shaven pussy!"

Jan smiled and said, "Deal! We should go to a beauty supply store and buy a 'peanut', it's a small hair trimmer that will make the shaving part easier."

"Let's go," I said.

We both got dressed. I noticed that Jan didn't wear underwear again so I decided I wouldn't either. It felt kind of weird going 'commando' but pretty sexy too. What was really sexy was knowing that Jan had nothing on under her sun dress. We found a beauty supply store nearby so we walked over there to make our purchase. We walked home with our purchase while holding hands feeling rather giddy knowing what was coming. When we got home we both stripped down immediately and walked into the bathroom. I dashed into the kitchen to get some old newspapers on which to collect shorn hair and returned and spread them out on the floor.

Jan had me stand on the papers as she began trimming my pubes with the trimmer. She worked around my now hard cock (the vibrations were invigorating!) and scrotum trimming me until all I had was stubble. Jan and I traded places and I trimmed her already short pubes to stubble. When I finished with Jan she told me to get into the shower and wash my pubic area with very warm water to soften the stubble. I scrubbed myself thoroughly and then rinsed off the lather with fairly hot water. When I was finished, I dried everything except for my pubic area.

When I was dry, Jan pulled me over to her again and had me lean against the bathroom vanity. She lathered me up with shaving gel, changed the blade in my razor and set about shaving me clean. She was pretty deft with the razor and had me smooth as a baby's behind in about 15 minutes. I climbed back into the shower followed by Jan so she could soften her stubble and I could clean off any residual foam. She offered me the razor but I chickened out and let her shave herself.

I enjoyed the show as Jan cleaned her pubic area of hair. I also marveled at the feeling of my own pubic area sans hair. When Jan finished her pubic area, she handed me the razor and said that I needed to shave her backside. I took the razor a little nervously, spread a little shaving gel around her bunghole and then gently shaved her. When I had finished, Jan got into the shower one more time to clean off the freshly shaved areas.

"I think you need to sit on my face so I can enjoy your new look," I said.

Jane laughed and replied, "I think you are right!"

We went into the bedroom and I jumped onto the bed and laid on my back. Jan followed close behind and then straddled my face. I pulled her down and enjoyed her smoothness as she wiggled around on me. I began lapping at her clean pussy enjoying the fact of no hair. After a few moments Jan attacked my erection with a vengeance taking me deep into her mouth. She lifted her head long enough to say, "This is great! No nose tickling hairs!"

In no time at all we were both feeling our orgasm gearing up and we both climaxed within seconds of each other. Jan crawled off me and then laid in my arms as we hugged and kissed. After a while we both nodded off and slept for a couple of hours. When I awoke, I discovered that Jan wasn't next to me. I got up and wandered into the living room to find her sitting, curled up, in a chair reading a book while listening to music. I greeted her, sat on the sofa and asked her how she liked the book.

"So far I love it. Has he written many?"

"Yeah, that's the first in a series of four. I have all of his books so you can finish the series at your leisure," I said. "What would you like to do this evening?"

Jan stood, set her book down, walked over to me, straddled my lap and sat down. She looked into my eyes with a mischievous look and said. "I want you to fuck my ass again while I'm leaning over the railing on the balcony. I want you to pound into me making me scream out while my orgasm hits me! Then I'm going to take you into my mouth, get you hard again and then you are going to pound my ass again until I have a monster climax! How does that sound to you?"

I looked into her eyes, smiled and said, "So, you just want to spend a quiet night at home. I think we can do that. Did you want to eat first or just jump into the evening's entertainment?"

Jan replied, "I think I would like to jump into being entertained. I took the opportunity, while you were napping, to cleanse my colon, I have a tube of KY right here and my ass is just itching to get fucked again!"

I pulled her face to me and kissed Jan deeply. Between kissing a beautiful naked woman and listening to her talk about pounding her ass, I had an erection for the ages! Jan broke the kiss and then strolled, sexily, towards the balcony. I stood up and followed her out. She set the tube of KY on the table and then leaned onto the railing with her chin resting on her hands which were on the railing. She arched her back a bit causing her ass cheeks to part giving me a view of her pussy and anus.

I knelt behind Jan, pulled her ass cheeks apart and then buried my face into her cleft. When my tongue reached her rosebud, I licked on and around it getting it nice and wet and I caused Jan to moan loudly. After a while I began prodding Jan's anus with my tongue as I tried to push it into her as deeply as I could. I tongue fucked her ass for a few minutes while I sank a couple of fingers into her sopping vagina. As my tongue tired I replaced it with the two fingers that I had put into her pussy. As my fingers prodded Jan's ass, she moaned even louder as she pushed back against my hand. After another five minutes Jan told me, "Fuck my ass Jimmy! Fuck me hard and fast!"

I pulled my fingers from Jan's ass, grabbed the tube of KY, squirted some into Jan's gaping asshole and the spread a good deal on my throbbing cock. When all was lubed up I positioned my cock at her backdoor and firmly pressed forward, sinking my entire length into Jan's ass in one motion. "AAAUUGGHH! OH, FUCK, JIMMY! FUCK MY ASS! FUCK IT HARD!" Jan cried out. I began fucking Jan's ass with a fairly quick tempo pushing into her hard every time I sank into her. It was all very primal and animalistic and very erotic. Jan's tits were swinging to and fro as I fucked her and her moans and groans were nonstop.

"JIMMY! FUCK ME HARDER, JIMMY!" Jan cried out. I grabbed her hips tightly and began pounding into her with everything I had. I felt my climax rising and cried out to Jan that I was going to cum soon. Jan cried out, "ME TOO! OH, FUCK! I'M CUMMING, JIMMY! FUCK MY ASS, JIMMY! I'M CUMMING!!!" I felt her rectum start to squeeze and pulse on my pistoning cock and then felt my orgasm strike and pulse after pulse of semen shot into Jan's bowel. I grunted and groaned with my climax and held myself tight against Jan's ass.

When my cock stopped spasming, Jan stood up, turned around and kissed me deeply while hugging me hard. When she broke the kiss, she looked into my eyes and said, "Jimmy, you are the best lover I have ever had! Now sit down on that chair so I can suck your cock back to life!"

I sat down as Jan kneeled before me and then she took my half hard cock into her mouth sucking it all of the way in. I couldn't tell which was better, her ass or her mouth. She was sucking and licking me like a woman possessed and before long I was hard again.

Jan stood up and then pulled me up from my chair. "I want you to fuck my ass again just like you were before we came. I want you to fuck my ass raw so when I'm in my meeting tomorrow I will feel it tingle and hurt." She then turned and leaned on the railing once again as I reached for the KY. "You won't need that!" Jan said.

I walked up behind Jan and pushed into her ass hard and fast, burying myself inside her. "Did you like that?" I asked.

"OH YES! FUCK ME HARD, JIMMY! FUCK MY ASS UNTIL I'M BEGING FOR MERCY!"

I began plowing into her again as her words brought out the lust in me. I grabbed her tits and squeezed them hard before I pinched and pulled on her nipples. I watched as her ass rippled every time I pushed into her. I let go of her right tit and then without really thinking about it slapped her ass hard with my right hand. The reaction was immediate!

"OH FUCK, SLAP MY ASS AGAIN HARDER!" Jan cried out.

I slapped it again with a mighty smack. She had two handprints in red now as her ass cheek glowed. She cried out for me to slap her again and again. Her right cheek was crimson when I had finished and before too long Jan yelled out that she was cumming! I could feel her rectum spasm once again as her climax hit her but I continued plowing away since I wasn't close. I fucked Jan's ass for another 15 minutes before I shot my wad, once again into Jan's depths. During that time Jan had several more orgasms.

When we had finished, Jan collapsed onto the balcony in a heap. I asked her, "Are you alright?"

She replied, "I'm wonderful! Thank you, Jimmy, for giving me exactly what I wanted. Will you marry me?"

I smiled at her and asked, "Seriously?"

"Yes, seriously! Will you marry me? I want to spend the rest of my life with you. These past few days have been the happiest of my life. I think we should get married as soon as we can because I love you."

I looked at Jan with a beaming smile and said, "I love you too! What time is your meeting tomorrow? Perhaps we can get married afterwards or something!"

Jan tried to stand up but was a little wobbly on her legs, so I took in my arms, carried her to the bedroom and laid her lovingly on the bed. I laid down beside her and stared into her eyes. I gave her a love peck on her lips and then asked, "So, I think I will give the airline my 2 weeks' notice tomorrow and then plan our honeymoon. Where would you like to go?"

Jan smiled and said, "I want to go anywhere and everywhere as long as I'm with you! Can we start with Paris? I've never been there but have read so many stories about it."

"Paris is a wonderful start! I've been there many times as it's one of my favorite places. From there we can go south to Provence and then on to Italy to Lake Como and then south to Rome. It will be marvelous."

"I love you Jimmy. Wait...do you want me to call you Jimmy. I should have asked."

"I love it when you call me Jimmy. It reminds me of the girl I had a crush on all of those years ago. You are the only one who calls me that so it's a special thing to me. By the way I love you too!"

We cuddled up in each other's arms and fell asleep blissful in our love for each other. When we awoke in the morning we showered, got dressed, ate breakfast before we set off for our different jobs. When I got to the airport I found my supervisor and told her of my intent to resign my job. She asked me why I was giving up my career and I told her it was never a career for me but it was a stopgap until something better came along. I told her I was going to get married and see the world! The manager stopped into baggage service to verify that I was, indeed, resigning. When I affirmed that I was he told me that he was sorry to lose me as I was a fine agent. I thanked him as he left.

I asked for and got an early release from work so I could head home as soon as possible. I had given Jan a card and key so she could get into the building and into our condo. She hadn't returned by the time I got there, so I stripped myself naked and laid down on the couch waiting for her. When Jan walked in she smiled when she saw me, stripped off her business clothes (I noticed she had not worn underwear!) and jumped on top of me on the couch. We held each other tightly as we kissed passionately.

I asked her, "Should we walk over to the courthouse and see if we can get married today?"

Jan smiled and said, "I think we should. What should we wear?"

I replied, "As little as possible!"

We got dressed and strolled to the courthouse. We discovered that it would be no problem getting married so we bought the license, were ushered into a judge's chamber and were married, using a couple of clerks as witnesses. We stopped at a sushi bar for lunch and held hands while we ate.

I looked Jan in the eye and said, "I think I'm the happiest person in the world right now!"

Jan shook her head and said, "Sorry, you are the second happiest person in the world because I'm the happiest! I told my bosses that I was quitting, today. They were a little upset until I told them why and then they were nothing but gracious in their happiness for me. I think I have had enough to eat. What do you say to going home and consummate our marriage?"

I grinned and said, "Now I'm the happiest person in the world!"

Please rate this story
The author would appreciate your feedback.
Share this Story

Similar Stories

That's What Friends Are For Justin's best friend Samantha will do anything for him. in First Time
New Girl in Town Pt. 01 Will the arrival of a new girl at school change his luck?in First Time
Back Home A trip back home changed their lives.in Romance
Just the Tip He's too big for her tight backdoor, but just the tip...in Anal
No More Wasted Time Not who he expected to see at his daughter's wedding.in Romance
More Stories