Jill and I Ch. 08-10

Story Info
The finale... will love win out?
11.8k words
4.77
18.3k
16

Part 5 of the 5 part series

Updated 10/18/2022
Created 10/28/2012
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
deadeye_76
deadeye_76
1,653 Followers

This story is loosely based on a true story provided me by a Lit reader. He told me to do with the information what I wanted and to write a story about it. It's a romance and I will provide it in five parts.

Main Cast
Dennis, 25 years old, 5' 11", 175 lbs, brown hair, blue eyes.
Jill, 30 years old, 5' 7", 120 pounds, brown hair, blue eyes.
Gina, 30 years old, 5'6", 140 pounds, auburn hair, green eyes, Jill's best friend.
Denise, 25 years old, 5'1", 105 pounds, brown hair, brown eyes, Dennis' friend and works with Dennis.
Mike, 27 years old, 5'10", 190 pounds, black hair, brown eyes, Denise's boyfriend.
Jeff, 33 years old, 6', 190 lbs, brown hair, brown eyes, Dennis' brother.

Previously:

After meeting with Jill's therapist, who she had been seeing for three years due to her rape and becoming a stripper and problems with men, we agreed to have a date. The psychologist said that she wanted us to date and discuss and talk about everything; all our secrets. I did feel much better now that things were in the open, but I was still thinking about what it meant to feel this way about a woman who had made guys cum in their pants by dry-humping them in nothing but a g-string; although I got hard thinking about her doing that to me. Oh, well. We'd find out over the next couple of weeks.

Chapter 8. We Try Dating

December 30th, 2011

Our first date was an easy one. We both went to happy hour and everyone else tip-toed around the subject of the two of us and we didn't say anything. When we left, however, I know that there must have been a lot of discussion of what was going on between us. We left together and went to dinner, which added to the rumors of our break-up and then reunion.

Things went well and we discussed everything except what we really needed to talk about. Finally, as we were paying the check, Jill looked up at me. "Want to go for a walk?"

I agreed and we went outside. It was a little cold and I could tell that Jill was going to get cold so I stopped us at the entrance to the restaurant and did the last three buttons on her coat. She stared at me. "What?"

She smiled. "I remember reading in one of those girly magazines that when a man buttons up a woman's coat it means he's a good guy, and cares for the woman."

"Girly magazine?"

"Yeah, I think it was Cosmo. You know Cosmopolitan? The one that also publishes all those lists about who wants what in bed and the results of all those sex surveys?"

"Yeah. I've seen it on the newsstands. Pitiful."

Jill smiled. "Yes, I agree." She took my hand. "Thanks for buttoning up my coat."

"You're very welcome."

We walked out along the sidewalk in front of the collection of shops and restaurants that were in the complex. I decided to start the serious talk. "So, Jill, can I ask you some of those tough questions now?"

She turned to look at me, her face a mask to me in that moment. "Sure." She didn't sound sure.

"I want to know about your stripper years."

Jill turned to me. "How about we call what I did exotic dancing? Can we just call me a dancer? I'm still trying to get over that part of my past and stripper just sounds too, I don't know, vulgar now that I'm out of it. At the time, it was no problem, but when I'm trying to put it behind me, well, how about we just say dancer."

"But isn't it vulgar?"

"Well, it doesn't have to be. Everybody sees nudity everywhere. It can be beautiful until you put leering assholes out there, who treat women terribly and want table dances while they slobber all over you. Can you please just say dancer?"

"But isn't that what strip clubs invite? Don't they invite men to look at women like nothing but sex objects? Don't they draw those types of men?"

"Yes, I guess they do. When I was 18, I never thought of it that way."

I conceded the point about dancer. "Okay. I want to know about all those awful things that I hear about in connection with dancers. What about prostitution, drugs, terrible boyfriends, etc.?"

Jill took a deep breath. "You mean you want to know if I did any of those things."

I glanced over at her as we continued to walk. "Well, yes."

"I have never prostituted myself. I never had a boyfriend while I was dancing, and I did try a couple of drugs with Gina, but it wasn't what I wanted to do with my life, so after I tried them, I never did them again."

I thought about that. "What was it you wanted to do with your life?"

She pondered that for a moment and I felt that maybe she was thinking too much and trying to form what she thought I wanted to hear, but then she answered. "I wanted to get out of that shithole. I wanted to get away from my mother, that neighborhood, and that fucking life. I wanted to get a college education, get a decent job, and maybe have some kids that I would raise better than anyone in my area ever did. I knew all along that I had to get out of there before it consumed me."

I stopped and looked over at her. "You want to have kids?"

She gave me a weak smile. "I did. I'm not so sure anymore. I have a good job and I'll be 31 next month, so I guess I'll have to change my goals."

I thought about it. "So did you ever date or go out with anyone from the strip club?"

She looked at me carefully. "Yes. I did date one guy who I knew from working at Wendy's who started coming in because he knew me and Gina. I dated him for about three dates. After he realized that 'dancer' didn't equate to 'whore', he left and I never saw him again."

"Oh, sorry." I pulled her hand to keep her walking and before I could ask another question she asked me a couple.

"Have you ever done drugs? How many women have you had sex with?"

I stopped again. "I have never done illegal drugs. I was always playing sports and it was important to me to stay clean as an athlete. I also had a good friend who got completely messed up with drugs in high school so that turned me off to them." I took a deep breath and thought about the second question. "How many women? Let me see...." I started counting on my hands and made several round trips before she understood that I was joking and trying to lighten our conversation.

"Stop!" She giggled and slapped at my hands.

"In truth I think it's about 6. I was always a one woman at a time kind of guy. I was always involved with the women I had sex with. All my sexual relationships were ones with women I ended up dating for 6 months or more. I didn't go out with someone just for the sex, plus, I was never good at picking up women."

She looked at me seriously. "Same number for me."

I stared at her. "Really? Only 6?"

She shrugged her shoulders. "My job didn't allow for it at the club, and then at college I had a few boyfriends, but I was trying to graduate. Then when the one guy I was really interested in told his friends, I stopped dating and have only had sex with one individual since then – you."

I stared at her. "Wow! I mean, I thought that, well, you know, as a dancer...."

She sighed resignedly. "I know, everyone thinks that dancers are out fucking everyone. They pick up the rich guys from the club and fuck them for money. Or they are sleeping with their girlfriends and then hook up with hot guys so that they can have those DVD grade threesomes. Yeah, I know, I've heard it all before. Some actually do that, but most of them I knew did not."

"Sorry."

She took my face in her hands. "Don't be sorry. Dr. Benson said we needed to be honest with each other and if that's what you were thinking, then we need to get it out in the open. I have never done that and I didn't fuck around."

"Okay. But you seem to like sex so much, and yet you managed to have it so seldom."

"I know, it sounds weird from someone who was almost naked every night for a while. But I was so turned off to men at that time because of my experiences with my mother's boyfriends and the assholes that I met in the club. I was really just taking out my anger on them, that's why I loved seeing them cum unexpectedly in their pants. At least that's what I got out of my therapy with Dr. Benson."

"Oh, I see." I understood it a little, but not completely.

We walked toward our cars, both of us now thinking more than talking and we said good night without a kiss. I just walked away. I knew she wanted me to kiss her, but I couldn't. I knew that if I did, I would end up back at her house in her bed. Once she kissed me I would want her too bad. And I was thinking that my feelings for her were not enough to overcome the problems I had with living the rest of my life with a stripper. I couldn't face that right now.

I drove home and thought about what she had said. I was amazed at how little sex she had had considering she was g-string dancing in front of so many guys.

When I got home I called Denise. She made me promise to call. It was only 10pm so I figured she'd be up. When I told her some of the basic facts, she gasped. She, too, was shocked at the revelation about the number of lovers and laughed, saying that she had more than that in her sophomore year in college. I called her a slut. She laughed and told me that I already knew that.

December 31st, 2011

New Year's Eve had finally arrived. I took my time that day and watched some football alone and then got ready for the party at Denise and Mike's. It was not going to start until 9pm since we all planned on being there late.

At 8:30 I showed up at Jill's house. I rang the doorbell and a vision answered the door. Her brown hair had been put up on top of her head with the exception of a few loose tendrils that had been purposely left dangling to catch the eye. The dress she was wearing was some sort of shimmery white material that was transparent in strategic places. It had a lining that covered her from her hips to the bottom of the skirt and from just below her breasts to just above them. It was see-through around the midriff and shoulders and showed off her delightfully slim waist. It was form-fitting (I was never good at describing women's clothes) and came down to mid-thigh. She had on matching shoes that had about three inch heels and on her 5'7" frame with her legs, made her look tall, long-legged, lithe, lean, and fucking scrumptious. To hell with the party, I wanted to keep her to myself all night. Only my misgivings about being with her long term kept me from that – but just barely. After all, my dick had a short memory.

I held out a single coral rose, the color of which I knew she loved, and looked her up and down dramatically for effect. "Wow! I have a date with a goddess."

She blushed, which is rare for her, and smiled. "Thank you. I think I did pretty well myself." She grabbed and wiggled my tie. "Do you want a drink first or should we just go?"

I looked into her eyes, leaned over, and brushed her cheek with my lips as I leaned toward her ear. I whispered breathily "If we don't leave right now, I can't be held responsible for my actions."

She wrapped her arms around me and hugged me hard. "You can do whatever you want with me. I'm yours. You know that."

I leaned back and looked at her. She stared back at me, her lips smiling, but I could feel the slight trembling in her body. She wanted it as bad as I did, but I was not past my reservations about where I was going with a stripper. I had told myself to take it slow until I could either get used to it or come to the realization that I was never going to get past it. The physical relationship would just interfere with my thinking. I knew that like most guys, my intelligent thought was interrupted by any blood flow to the lower regions. I didn't want to lead her on, but I had to get used to the idea and she knew it. "I think we should go now, before we don't make the party at all."

Jill looked a little disappointed - then smiled and reached for her wrap. She handed it to me and I wrapped it around her shoulders. As we headed out the door she said over her shoulder. "It wouldn't be a total loss to miss the party." She wiggled her butt at me.

Inwardly, I was fighting myself. I wanted to throw her down and fuck her right then and there. I had had sex with this woman constantly for a couple of months and I was almost addicted to her physical attractions. I fought off the last part of my desire to rip her expensive dress off and fuck her right there in the living room and followed her out the door. However, I did slap her on the ass. "Temptress!"

She giggled and we managed to get to the party without messing up our clothes. Once we arrived, we were greeted by some of the folks from work and some of Mike and Denise's other friends. We got into the mix and I could see the glances that Jill was getting from some of the other guys. Most were just guys, checking out a beautiful woman, and then they would move on, but there were a couple who were almost leering. I mentioned it to Jill. She smiled. "Welcome to my world. I have had this problem my entire life. Sometimes it's good for the ego, but mostly it's just annoying – and sometimes dangerous."

I noticed that Jill was only drinking soft drinks and water. I brought it up. "Not getting drunk tonight?"

"I'm a little tired of that so I think I'm going to just enjoy being in your presence." She winked and I rolled my eyes.

Denise was her typical flirty self, flitting amongst her guests, laughing and giggling all the while. At one point she was with Jill and I and she was telling a story. She kept grabbing my arm and Jill noticed. She knew that Denise was a touchy/feely sort of person, but she was picking up on something else. Denise finally finished the story and reached up and pecked me on the cheek. "See you later."

Jill leaned over to me. "That girl would sleep with you in an instant." I turned my head to look at Jill and she seemed to know. "Or have you two already been there and done that?"

I took Jill by the arm and led her over to the side of the room like we were getting more drinks. "We have not actually, you know, had sex – I mean, you know, we didn't actually – fuck." I looked up at her and she had this strange half smile on her face as she studied me.

"And that means what exactly?"

"We gave each other oral sex." I looked at Jill to try to gauge her reaction. "It was before we were together." I added that quickly, afraid that she would assume the worst about me and we would be starting from square one.

She leaned over and kissed me. "I guess I'll have to keep my eye on you. You are just too good a catch to go unnoticed by the ladies."

I chuckled. "I wouldn't say that. I've never had women come on to me."

She kept looking at me with a funny smile. "You are young and just haven't been hanging out with the young, single, aggressive women. They would have been all over you. You are young, responsible, grounded, handsome in a nice Midwestern guy kind of way, and are excellent father material. Trust me; they would be gobbling you up."

"You mean they don't all want the bad boy?"

"At first they do, but women are more grounded when it comes to evaluating men than vice-versa."

"Oh, really?"

"Absolutely. Trust me, women are more subtle, but they would be make it known that they were available for you."

"Okay, thanks. I love it when you pump up my ego. And when it comes to Denise, she's a flirt, but I would never do anything to endanger her engagement to Mike. She's my best friend." I looked at Jill and she raised an eyebrow.

She put her arm through mine and said dramatically. "I'm not going to let you out of my sight the rest of the night in the presence of these hussies."

We both had a good laugh at that. We were at least able to joke with each other. At midnight, the ball dropped and everyone there grabbed their significant other and we all kissed. I reveled in the moment, enjoying the tender kiss that Jill and I shared. It was our first really decent kiss since our blowup last weekend and we both did it softly, but wetly and I think she moaned as we did. I popped a boner against her leg and she rubbed against it.

Suddenly, there was a lot of commotion and we were all herded outside by a group that wanted to celebrate in the street. We made our way down the stairs and everyone was partying in the street, blowing those stupid little horns, banging on anything they could find, and yelling. It was funny and ridiculous at the same time.

It was now about 12:30 and we were enjoying our time out in the cold, but I could see that some of the women, including Jill, were not as protected as others from the elements. I gave Jill my jacket and she put it on. She wanted to walk down the street away from the partygoers and enjoy a little of the night air.

We walked and she asked me why we really didn't have sex before we came to the party.

"I don't know."

"Yes, you do." She stared at me with those x-ray eyes, looking right through me.

"I'm still a little afraid of what I'm getting into."

"Oh." She seemed disappointed, and we just walked for a few moments.

When we got to the end of the block we turned around and then I sensed sudden movement to my left. I turned my head to be confronted by two guys, one of them brandishing a knife. Jill saw them, too, and we both stopped immediately. The guy with the knife was white, about 6' tall, skinny, had terrible acne, very young, and had eyes that darted around so quickly it looked unreal. The other guy was black, about 5'7", also skinny, and looked more dangerous because of the nasty grin he had as they accosted us. The rest of the people from the party were over 100 feet away and most were going back inside. It was not a bad area, so I was shocked to see these two. The one with the knife spoke as they spread out in front of us, him in front of me and the other in front of Jill.

The guy with the knife spoke to me first. "Gimme your wallet." Then he turned toward Jill. "And take off all your jewelry." We were both frozen to the spot, looking at the two of them, so he repeated his demands. I reached for my wallet and pulled it out. I only had about 50 bucks in there, but I hated to have to cancel my credit cards and get a new driver's license. I didn't know how expensive Jill's jewelry was, but fortunately her purse was in the house. I was also calculating the danger involved in fighting back. It didn't appear to be much in our favor. If I could hold them off, she could run back to the party, but in her heels and that dress, it would be difficult. And that would leave me to fight off and get away from two guys, one with a knife. Instead, I hoped they would just take the items and go, so I held out my wallet and Jill did the same to her jewelry. She was very quiet and shocked, but looked outwardly calm.

The black guy stepped forward and quickly reached for my wallet and took Jill's ring and earrings, which was all the jewelry she had on. The guy with the knife leered at Jill. "I think maybe we need to try out the pussy on this one." He pointed with the knife. "I bet she would just love my nice big dick, eh?"

I glared at him and said nothing. I think he was goading me, but I couldn't be sure. I was now getting ready to fight him. If he got any closer, I was going to go after him. I couldn't let them do anything to Jill.

The black guy moved around behind us. "Yeah, she's got an ass on her that I would love to tap."

I tried to stop it. "You guys got your loot. Take it and go before somebody comes along and sees it happening and calls the cops."

The guy in front of me sneered. "Fuck you. We'll do what we want, when we want, and right now I think we want some nice tight prissy girl pussy."

I tried to keep them both in sight, but the black guy was circling behind me and I wanted to keep my eyes on the knife. I didn't want to fight with Jill here, but it might come to that. There was no way I was going to let her be raped again.

deadeye_76
deadeye_76
1,653 Followers