Making Good on My 2nd Chance

Story Info
Chance meeting leads to a 2nd chance with an old girlfriend.
2.7k words
4.21
13.2k
6
Share this Story

Font Size

Default Font Size

Font Spacing

Default Font Spacing

Font Face

Default Font Face

Reading Theme

Default Theme (White)
You need to Log In or Sign Up to have your customization saved in your Literotica profile.
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

Kayleigh and I were a couple back in our early 20s, but we just weren't the right match when it came to a long term commitment like marriage. We both moved on. She got married and had 2 boys while I moved from relationship to relationship enjoying successes and defeats as we all do.

When we were together, she was 21 and I was 24. We had our fun for sure in bed, but because she was so attractive and my confidence was lacking, she pretty much ran things when it came to sex. Don't get me wrong, I enjoyed every minute of it as she was always in shape and she was never holding back. That said, I always wondered after our breakup how our sex would have been if I were the one in control.

11 years after our parting ways, my opportunity came about. It was a Saturday night in June at a baseball game. Kayleigh had brought her 2 sons to the game and I was there with my nephew and with no planning whatsoever, they were sitting in the row in front of us.

We recognized each other immediately and because we were there 45 minutes before the game, we began chatting it up with ease. The 3 kids seemed to take care of themselves as I discovered it was her weekend with the boys as she was in the middle of a separation and she wanted to do something fun. Over the course of the day, we enjoyed our team winning the ball game and we exchanged numbers to catch up even more later on.

I did not call her until Thursday night and it was like I was a teenager again with anxiety whether I should call her and if I did, would she even want me calling her. The sound of her voice on the other end pushed that anxiety away and after about 5 minutes of small talk, I asked her if she'd like to meet for dinner the next night. She hesitated at 1st saying that she was still married and that she was not sure if she should, but I reassured her that we were old friends catching up and she went along.

We decided to meet up at a local casual dining establishment. Seeing her in her light blue sundress sent waves through my brain. I realized it the previous weekend, but tonight without kids in the mix, my full attention was on her.

We sat across the table from each other and each ate a salad as we talked. I had asked her about her life and she was pretty happy about things except for her failing marriage, but professionally she was content. She asked me about my life and I told her about my being single for almost 6 months and that I was always up for new things.

She then asked "Have you ever thought about me?" I responded without hesitation "Yes, of course."

"What do you think about?" she said with a devious smile

Put on the spot I felt, I whispered my answer trying to be discrete since we were at the restaurant "Well, I definitely remember everything under that dress."

Her blushing was obvious. I was not sure if I had gone too far or if I had struck gold, but her not objecting made me feel confident of the latter.

She then said "I want to tell you something, but I don't know if I should or not." I cued her on "Say what you wanna say. We are grown ups."

"Well, the only man I have been with since you, has been my husband, and I think I miss you more than I do him." Her saying this so straight forward took me aback and I realized I had her in my sights and it would not take much for me to take advantage of my 2nd chance.

I must have shown some satisfaction in my reaction, because she asked "Well, are you gonna say something?" I stuttered at 1st, but I did finally respond. "Wow. That wasn't what I was expecting at all."

She was embarrassed at what she had said and my reaction, but I reached across the table and took her hand, as the feel of her chilled wedding ring reminded me she was still married, but vulnerable. I looked into her eyes and said "Kayleigh, I have missed you too." The joy in her eyes was vibrant.

We exchanged smiles as we stared at each other and I paid our check and we walked out to the parking lot. I insisted that I drive and we leave her car there and we could pick it up there later on. She asked why, and I said outright "Your car has GPS and I know how us guys are. Your husband may find my address if you were to drive there." I could see the light bulb go off in her head as she realized that I planned on taking her back to my place. I opened the passenger door for her and I could feel her shaking as I assisted her into my car. I closed the door and as if in a sprint, ran to the other side, got in and drove home.

It was sunset as we arrived at my house and I held door open for her and escorted her in showing her my modest estate and asked her if she wanted anything to drink. She politely declined and with that I ran my right index and middle fingers across her cheek brushing back the curly blonde streak of hair away and moved in for a seductive kiss. We melted into each other as my hand went to the small of her back as her arms wrapped over my shoulders and it was as if we had never been apart.

It was then I showed her something new. I pulled up the back of her dress with no invitation and got a good squeeze of her perfect ass. Our kiss broke and the look of shock on her face was priceless. I then proceeded to pull her dress over her head as she stood there in just her bra and thong in her sandals.

I took in the beautiful view and it took great effort for my jaw not to drop. I unbuckled my belt and undid my jeans and let them fall to the floor. My raging hard on was completely free and her eyes dropped sights on it as she said "Wow, this was fast."

In our past she had been the 1 to initiate, carry out and finish the conquest. Tonight, she was my prey. Standing there in front of her I asked "Is it true that wives don't go down on their husbands?"

She shyed away and said "Shut up!" She went to her knees looking up to me and took my cock in her hand and began worshipping it with her eyes, hand and finally her warm mouth. The feel of her fingernails on my nuts sent a rush through my brain as my cock was being bathed by this sweet angel. Looking down to her as she worked it, I thought to myself I may be in heaven. When she opened up her sparkly blue eyes with my cock in her mouth, it took all I could not to release right then and there. My hands ran through her smooth silk hair. Her muffled moaning was just another trigger that I had to fight against.

With firm grip of her hair, I pulled her up to stand before me and I kissed the mouth that had my cock in seconds earlier. Upon breaking our messy kiss I said to her "I have thought about this for years Kayleigh." I turned her around and unclasped her bra and without thinking, grabbed her thong and with little problem, ripped it clear off of her. Her shriek at her sudden full nudity was evident as I saw her shake as she pleaded "David! What are you doing?"

I looked her over and loved how her body had fully matured since our parting. Her breasts were full and her nipples were rock hard and pointed. Her pussy was clean, and to my liking, she had no stretch marks or scarring from her pregnancies. I had to fuck her like I had always dreamed.

I walked over to her and took her hand, "Let's go to my bedroom." I threw her onto the bed and she laid there on her back hungry for me as I hungered for her. In our past, this would be when I would worship her by devouring her sweet juices and make her feel like a queen. Instead I stuck my raging cock right in her bareback and she accepted it, but the panic on her face could not be disguised. Her left leg went over my shoulder as she pleaded "David, wait, I'm married. Please hold up." I disregarded this and rammed it deep and hard hearing my balls hit her ass. I changed the pace and included some swirling as her pleas turned into begging moans. I pushed deep into her and fell on top of her as I kissed her on the lips. She kissed back hard and wrapped her arms around me as I pumped myself inside her slowly as we both enjoyed the feelings aroused by our mutual fucking.

I then stood up and pulled out of her and shot a load across her stomach and breasts. I could not hold it in any longer and tonight was not just about her satisfaction. It was about mine, but I was not finished with her yet.

As I said earlier, I had a history of enjoying her sweet pussy. I laid down on my bed next to her and she thought we were going to cuddle as she complimented my new attitude "Baby that was great. I would have never believed you would be so forceful." I took my hand and cupped some spunk and put it to her mouth. "Take it Kay." Her defeated eyes spoke volumes as her mouth open and she slicked my hand clean. Motioning toward my recovering penis with my eyes, I directed her to worship it some more, but this time, I wanted some of her as well. She climbed on top of me as her pussy and ass rested above my face, I had to give it a firm slap. Her ass was perfect and er fucked pussy was even more delicious than I imagined.

As my tongue took in her juices he moaned on my cock and began talking freely when she did not have her mouth full. Some of the things she said were: "If you were like this before, I would have been the mother of your children." "My God, l have never felt like this with you." "Your tongue is still amazing."

It was then I did something I never dared try years back.

My hands had roamed the entire time across her sweaty back and ass as we 69ed, but without any thought, my fingers began exploring her clean brown little eye. Her attention to my cock stopped as a hush went over the room as her body tensed around my exploration. She said as if in pain "David, o god, you are..o god." My fingers delved deeper into her tight ass as I realized how her mood had completely changed. I pulled out my fingers releasing the clutch after such a brief investigation. I wanted to see her beautiful face after my mini-invasion.

The look on her face was priceless with a mix of disbelief as to what I had done along with what I judged a craving on her part.

My cock was back to rock hard status as I asked her if she'd like some Vaseline? She nodded yes and I told her "It's in my medicine cabinet. Go grab it and bring it here." She asked, why can't you get it?" I responded with the devil in my voice "Because I want you to know that when you are bringing me the Vaseline, you are giving me your precious little ass."

The stunned shock on her face was only multiplied by her complete silence for about a minute as I stood from the bed stroking myself. She then got up on her wobbly legs and walked to my bathroom as I could hear her opening my medicine cabinet. She walked back in defeat with the bottle of jelly in hand. With tears in her eyes "David, I have never done this before." I took the bottle away from her and said "We all need 1st times in life. This will be yours. I will be gentle. I promise."

She stood there as I put 2 fingers in and got a healthy portion on them. "Kayleigh, I remember you being so strong when were together, but maybe I was just too weak. Get on the bed and keep your ass in the air."

She crawled on to the bed ad was on all 4s like a perfect bitch in heat. Her face away from me, her beautiful ass was a sight for my lucky eyes. I coated her little brown eye with the lubricating goo as I stuffed 2 fingers in deep as she panted for relief. I pulled out my fingers and asked "Kayleigh, tell me where you want my cock?" Her breathing was heavy "Get it over with," I smacked her ass hard and she cried out in pain 'MY ASS! Fuck my ASS!" I did as she said and stuck it in slowly and gently as promised.

I did not pound it in because I did believe it was her first time and by how tight she was, I really did believe it for fact once I got in. Her screams were so loud that it was then and only then that my neighbors may hear us. I pushed down on the back of her head and buried her face in the pillow. Her screams were still apparent, but they were absorbed. I came in her asshole as I left my cock inside to empty itself which only led to more screaming. I pulled out my once again spent cock.

I laid next to Kayleigh spooning her from behind on my soiled sheets as she began to calm down. My cum began oozing out of her ass. She began muttering "I can't believe I came here with you. You are not the same man I loved all those years ago. You would have never done that to me back then." I responded by kissing her on her shoulder. "I have always wanted you like this and I thank you for giving me everything I have dreamed of all these years."

We stayed in that spooning position for almost an hour until it was around midnight and she got up as if to take a shower. I stood up and blocked her and told "You look too good to be showered here." She asked "What? What do you mean? " I explained, "I think it will serve you better to get dressed and for you to shower in your own home tonight?" She was very upset and began crying "Why are you being so mean to me? I'm so dirty. Please."

I told her "Get dressed and I will take you back to your car." It was then she remembered I tore up her thong. She put on her bra and dress and I walked her to my car. She adjusted herself several times as dress was sticking to her in places she was not comfortable with. I parked my car on opposite side of parking lot from her car and open door for her and helped her out. I enjoyed watching her walk of shame back to her own car. She sat in it for a few minutes and then drove away.

It was only 3 days later, my phone rang and it was her. I let it go to voicemail and I listened to her message "David, Thank you for the other night. I was wondering if you would like to come over to my place. Call me."

Kayleigh never reunited with her husband and she and I are very happy together. I made the best out of my 2nd chance.

Please rate this story
The author would appreciate your feedback.
  • COMMENTS
Anonymous
Our Comments Policy is available in the Lit FAQ
Post as:
Anonymous
1 Comments
AnonymousAnonymousover 7 years ago
C'mon....and Read What You Wrote

The story is a little vague and needed some fleshing out! But Jokesuit ...read your stories over before submitting them PLEASE! With a lot of THE"s put in where needed and other small error's corrected your story would be much more readable.

Share this Story

Similar Stories

Comforting My Neighbor's Daughter I fuck my innocent neighbor when she comes to me for comfort.in Mature
Oh Baby! What a Sitter! He was her sitter. Now he needs one, and gets something more.in Erotic Couplings
The Inheritance Ryan suddenly inherits his Uncle's fortune and his Assistant.in Romance
The Homeless Helping a young woman undo bad decisions.in Erotic Couplings
Back Together with His Ex-Wife 01 They get back together for the night or maybe morein Erotic Couplings
More Stories