Lisa and Jack Pt. 01

I took a two-week vacation and flew in to attend John's bachelor party that Friday night because he said it was important for me to be there. I almost didn't get to come because the company I worked for had just been acquired and the new management was in the process of really screwing things up for us.

I'm eight years older than Johnny, even though we met in college. I'd returned to school at age 27, using my GI Bill to get my degree after 8 years in the military. At the end of my second enlistment, I had tired of traveling and figured I could do better in the civilian world - which I did over the next decade after getting my bachelors. I had elected to enjoy the whole 'college experience,' so John and I had been roommates at Uni and remained good friends during the intervening years, keeping in touch and visiting each other often, with him providing me with moral support when my marriage fell apart, along with my job morale.

As luck would have it, a headhunter sensed there might be some discord at my current company and had called me. After a long chat, he convinced me to interview with another company in the same city where Johnny lived. As the firm offered to pay for my hotel stay and give me a nice per diem for food, I lined that up. I had them fly me in on the Friday morning of Johnny's bachelor party and, in doing so, I killed two birds with one stone.

When I arrived at the party, I was shocked to discover there were only four other guys there besides John and me (none of which I knew). Additionally, they were all about a dozen years younger than my current age of 41. The "entertainment" for the bachelor party arrived in the form of a cute, medium-height girl with waist-length, wavy chestnut hair, enchanting hazel eyes, a perky, turned up nose and a, to me, killer body.

I'm more a leg-and-ass man, preferring a tinier build, and this girl definitely had that, with small, but round, tits and a slim build. She seemed to know our host rather well -- trusted him, too. She didn't bring any muscle along! John instructed her to strip for us. The girl turned on the music and began to undulate as she unzipped the hoodie she was wearing (with nothing underneath). As she did, two of the guys quietly groused to each other about her tits being 'too small.'

They weren't, at least in my opinion. She was a B-cup, but today, guys appear to prefer 'thicc' or 'curvy' women and consider anything less than a D-cup as "flat." I don't happen to be one of them. The others mumbled into their beers about her lack of pulchritude, but did admit she "had a nice face, legs, and ass.".

Me? I kept quiet and sipped my beer until she finished removing her clothes. Naked, this girl -- Lisa, John had called her -- walked around to flirt, tantalize, lap-dance and kiss each of us, and she certainly had MY attention! She was built EXACTLY the way I liked 'em! While she got indifferent reactions from the other guys, I'd had a few more beers than I normally would by then and, feeling a little more emboldened, I put one hand around her waist to pull her to me, and used the other hand to grab her ass as she straddled me. This girl, Lisa, didn't complain, she just scooted right up, wiggled against my obvious hard-on and kissed me with far more passion than I expected from a hooker. Naturally, it got some hoots from the guys.

Feeling my oats, (or, rather, not feeling any shame due to the alcohol) I grabbed her long, thick hair and yanked on it, forcing her to arch her back and dip her head, providing me with perfect access to her tits. As I said, unlike other guys, I like them small. The ones with little tits always seem to have more sensitive nipples and a little bit more of a wild streak in them. I bit at the two buds atop her breasts once or twice and then kissed my way back up to her lips only to find her panting heavily.

"Hey, how about letting the rest of us get some?" chided the guy to my left.

I let her go and she let her hands glide down my body, stopping at my crotch as she slid off my lap. Lisa gave my erection a squeeze, causing the rest of the guys to chorus, "Hey, old man! Right on!" and "I think she likes you!"

When she got to the next guy, she immediately arched her back and tried to get him to bite her nipples, but he wasn't having any of it. He spun her around and smacked her butt cheek, telling her, "Lemme see that tight little ass of yours, sweetheart!" She squealed and then groaned when he thrust a finger in her ass, but then swatted his hand away when he got too rough.

The next half-hour pretty much continued like that, with her doing a dance, then making her rounds between us all, teasing, and the guys groping her, getting a little rowdier with each pass. After about an hour of dancing and flirtations, there was the offer for "a little more at an "extra charge." Nobody seemed willing to take her up on it, causing her to pout.

I held back because I was a little embarrassed at paying for sex at my age, but I finally gave in. I'd had less than a dozen fucks in the nine years since my divorce and she was a "hot little thing" in my book. Like I said, I like women with small breasts!

"I'll fuck you for $50." I told her.

Lisa squealed with glee and took my hand, leading me into the bedroom. All the other guys jeered and then went back to watching porn on TV while opening more beers. I was very surprised when she pushed me down on the bed and pulled off my pants and underwear in one yank. Lisa's eyes went wide and she smiled when she saw my cock. It throbbed as she slowly crawled up my legs, alternating kisses side-to-side as she gradually made it up to the object of her lust. In one move, the girl inhaled it and began to bob with a ferocity I'd never seen before. She didn't seem to have a gag reflex and had me cumming hard within minutes, sucking and swallowing it all down. Thinking it was over, I pulled out the fifty bucks and gave it to her.

Lisa batted it out of my hand, laughing in a deliciously evil manner. "What makes you think I'm through with you, stud?" she asked, throwing a leg over my chest and crawling up until her pussy was planted on my mouth.

I licked, sucked, fingered and fucked, making love to that little vixen. She didn't seem to want to stop and would climb on top of me and just impale herself onto my rigid tool and ride me like her life depended on it. I'd tried to stop her and inform her I had condoms in my pants pocket, but she was too far gone to take note of it. She rode me to three screaming orgasms before I felt that familiar tingling again.

I tried to pull out and ended up flipping her onto the bed so that I could control her movements and avoid cumming inside her without protection. She gave another demonic laugh and fought me a little, so I held her by her wrists, her hands above her head, pulled out of that wonderful pussy and jerked off over her tits before collapsing beside her.

Lisa surprised me by kissing me some more and playing with my cock. When it didn't rise immediately, she scooted down again and began to use that wonderful mouth to raise the dead. She was successful and we went at it again, with me mildly shocked that she didn't boot me out after I came!

Instead, we continued our lovemaking, with me worshiping her tight little body and putting her in every sexual position I could think of, making her cum about a dozen times to my three The girl had a kink streak in her a mile wide! We did it on the bed; with me standing and her ass hanging over the edge of the bed; with me standing, her head over the edge of the bed as I fucked her mouth, and then her tits as she rimmed me. When I sat in a chair, she simply straddled me and let me fuck her in the ass until she had two more orgasms.

"Jesus, you last a long time."

"I know. It was a complaint I often got from my wife, and most of the girls I dated."

"Really? Well, you won't hear any complaints from ME, stud! Let's go fuck in the shower!"

I made love to her there, cumming in her ass, then she cleaned me off and sucked me hard again before grabbing the shower head and lifting a leg, having me fuck her standing up. I nailed her until she couldn't hold her leg up anymore, came hard, and then almost fell. I lowered her to the shower floor and she sucked me hard again. We went back to the bed after drying off and I made sweet love to her and, after she came, cuddling with her, which made her cry.

"Shit, I wish I could take some pictures of you!" I said, wistfully.

"Why?"

"You're an absolute goddess!"

She laughed. "No, I'm not!"

"To me, you are! You're built exactly the way I love a woman to look."

She stared at me for a moment. "You really mean that?"

"Yes."

"Do you have your phone?"

"In my pants pocket."

She threw off the covers, revealing her body to me. "Go get it, stud! Take as many as you want!"

"Really?"

She giggled and nodded yes.

I got up and dug my phone out of my pants pocket. Three condoms fell out with it, and laid on the floor, completely forgotten. I think I took about fifty or sixty pictures of her, posing her and having her masturbate for me. Then she'd squeal and ask to see them. We snuggled again and went through the pictures, with her being very critical of her body, but with me complimenting her.

"God, I wanna fuck you again, Jack!" she said, throwing a leg over me as she sank down on my semi-erect cock. As she began to move, she pressed her hands against my chest and closed her eyes. I turned on my phone and made a video of her as she slowly fucked me. Her face held an angelic, ecstatic look as she undulated, increasing her tempo as she gradually built to a climax. When she opened her eyes and saw I was recording, she began to shudder, cumming hard.

I think we managed to get through at least half the kama sutra before I finally couldn't get it up anymore. I definitely got my money's worth and more! Lisa came in buckets every time I played with her tits, or told her how much I loved her nipples. I'm not sure how long we were in the room, but when I came out, two of the guys had left.

One other guy said he'd give her $20 for a blow job. She began to kneel in front of him and undo his fly, but he swatted her hands away while we all laughed. Getting up, she took his hand and pulled him into the bedroom with her. Given what she'd put me through, I figured they'd be there for another hour, so I opened one last beer and got on my phone, looking for my Uber app.

"Hey, Jack, don't worry about a ride," said Johnny. "I've got your back, bro!"

Not ten seconds after he said that, the door to the bedroom opened and the guy was zipping up his pants and buckling his belt as he came out, telling everyone it was time for him to go home. When the remaining guy declined to have sex with the girl, John asked the two of us if we could please clean up a little for him while he drove Lisa home.

*****

That following Sunday afternoon, John called me up at my hotel room.

"Jack, my man, I need to ask you something."

"Sure. Ask away."

"I need you to do me a favor, actually."

"What," I said, trying to hide the annoyance. I didn't have enough money to lend him anything if he happened to be short of cash for his upcoming wedding.

"I take it from my little party the other night that you like ladies that are a bit small up top."

I wondered what this was leading up to. "Yeah, I do."

"What did you think of Lisa?"

"She's a little taller than I normally like them, but built exactly the way I like. Dude, she was sexy as hell, and I sure as hell wish I could get a lady like that!"

"Good! So, you liked her?"

"Yeah. Why? And, you know, that bachelor party was pretty pathetic, John. I expected better from you."

He laughed. "Oh, that wasn't my official bachelor's party."

"It wasn't?"

"No, it was more of a going away party."

"Going away? For whom"

"My old girlfriend."

"What? Who?"

"Lisa."

"Lisa was your old girlfriend?"

"Well, yeah. That and she's going to be my sister-in-law."

"WHAT?!!"

"She's Meredith's younger sister. I started dating Lisa when she worked for me in the summer between her junior and senior year in high school. Then I met Meredith and fell in love."

"But you were still fucking her sister?"

"Every once in a while, yes. Meredith is more my style, though. Lisa has a kinky streak that drives me a little crazy. She told me she'd tell Meredith we were still fucking unless I kept doing her. Then, after she saw that Mer and I were seriously in love and were getting married, she asked me to find a replacement lover for her."

"You're shittin' me!"

"No, I'm not. She's actually kinda shy, unless she has someone around that she trusts. Her flirting used to drive me nuts, even though I was always the one that came home with her. It's one of the main reasons I couldn't continue with dating her."

"So, what do you want ME to do?"

"Well, I had her over the other night because I thought you five would be the best ones for her."

"And?"

"And, I told her to act like she was a hooker at a bachelor's party and see if she liked any of you guys."

"OK."

"She chose you."

"ME? Fuck, John! Does she have any idea of how old I am?"

"Yes, I told her. She's fine with it."

"How old is she?"

"Nineteen. She'll be twenty in four months."

"Christ, man! That's more than twenty years younger than me!!"

"Don't you think you can handle it? She said you were an absolute wizard in bed. But what cinched it up front was how you handled her when she was on your lap. She's a little self-conscious about her breast size."

"What's wrong with them?" I asked. "They're perfect!"

"Exactly. That's why she likes you."

"But Jesus, John, with her looks, she could get any guy!"

"Believe me, Jack, she can't. I don't get it either. When she does have a guy, she can flirt up a storm and attract every guy in the room. But when she doesn't have a guy, she can't seem to peel her flowery-self off the wall. The guys she does attract at those times usually either want a one-night-stand or they're turned off by her small tits and run off with the first big-tittied bimbo they find."

"So, what am I supposed to do?"

"Go out with her a couple times while your here, see if it does work out, then be her date to my wedding?"

"Holy fuck, Johnny! What are her parents going to think?"

"No parents, Jack, old boy! Just her, Meredith and their older brother, Nathan. He's my age -- and he was in college with us, as a matter of fact, though I don't think you ever met him. He's also the trustee for her parent's estate. When Lisa turns 21, her part of the trust fund will be released, and it's pretty substantial. Nathan's a broker and he's got his firm handling her money right now.

"John, I don't need her money. I'm not rich, but I don't need anything to make me comfortable. I'm fine, financially."

"That's why I was hoping it would be you, Jack. She's really got a thing for you; talked only about you during the entire trip home. She's been pestering me ever since I drove her home to call you!"

I sighed heavily into the phone. After my divorce and several false starts, I'd given up and hadn't been looking for a relationship, but now one was being thrown in my lap. With someone I considered almost perfect in every way. Lisa was very sexy, lovelier than I could hope for, adventurous, and erotic, too! Why was I being so reluctant and stupid?

"John, I don't even know if I'm going to be staying here yet. My interview isn't until Monday."

"Don't sweat it. If you go back, well, she graduates from college this spring and I'm sure she wouldn't mind following you."

"Graduates?"

"Yeah. She skipped third grade and is smart as a whip. What do you say, buddy?

"Holy crap, really? I mean, that's rushing things a bit, isn't it?"

"Just stating fact, my friend. Believe me, I talked to her about this a lot over the past two days. She's just as anxious over this as you are. What do you say, Jack? Just give her a chance, please?"

I mulled it over for a few seconds, sighed and then said, "OK. I'll go out with her."

"Call her? Right now, after we get off the phone?"

I laughed. "Why?"

"So she quits blowing up my phone every hour asking if I've talked to you yet!"

"Okay, okay. I guess I can call her now."

I got the number from him and then hung up. I took several deep breaths before picking up the phone again and dialed her number.

"Hello?"

"Hello, Lisa? This is Jack."

She squealed my name into the phone and then began to gush. "Oh God, I'm so glad you called! I was afraid that, well, after the other night that I wasn't, I mean, you wouldn't, well, you know..."

"Like you?"

"Yeah."

"What are you doing right now?"

"Uhhhh, n-nothing."

"Let's go out to dinner. I'm hungry and, when it comes to beginning a relationship, I don't really like talking on the phone all that much."

"OK."

"I'll pick you up in an hour then?"

*****

I arrived about 70 minutes later at her doorstep and she came skipping down the steps, dressed conservatively in a brown silk blouse and a white skirt, wearing sandals. Her makeup was a little different -- not as garish as it was the other night -- but it brought out her hazel eyes. Her long, brown hair was tied back in a ponytail and a single gold pendant of a dragons head with a ruby eye, hanging from a thin chain. Her collar had 3 buttons undone so that the medallion could be seen.

"You clean up nice," I joked when she got into the car. Lisa didn't say anything, but leaned across the console and planted a chaste, yet promising, kiss on my lips.

"I'm hungry, hunk. Let's go pig out!"

I laughed and drove to a steakhouse in the area recommended by the concierge at my hotel. We chatted amiably about a lot of nothing, feeling each other out. Finally, there was a lull in the conversation, so I decided to be the one to make the first move.

"Johnny says that the two of you dated."

She laughed. "Yeah, until my sister stole him out from under me!"

"How'd that happen?"

Lisa told me that Meredith had just gone through a nasty break-up and then had several flings with abusive guys.

"I asked Johnny to talk to her and straighten her out. You know, telling her that there are still good guys out there. John and I had a pretty open relationship, so I didn't mind when the two of them started going out together to talk and stuff. Hell, I'd been doing a couple of his friends. He even took videos one time! But, when he and Mer started talking more, I guess they found themselves to be soul-mates. God knows Meredith needed some stability in her life at that point."

"What about you?" I asked.

"What about me?"

"You're saying you don't need stability?"

She started to say something, then stopped and thought a bit.

"I've needed someone that I can feel comfortable with, which is why I've always been attracted to older men. I thought that was Johnny, but then I began to feel that HE was uncomfortable with things. A lot of times, he was more like a brother to me than a lover -- and I liked that. I mean, he was someone I could confide in. Someone I could vent to and not have them go all macho.

"Over time, he used to talk about his 'best buddy from college' and how he could come to you about things and not feel that his masculinity was threatened. He knew you'd "been there, done that" and respected you. He trusted you. As he talked, I told him that I wished I had a friend like that."

"Didn't you? In him, I mean?"

"In most ways, yes. But there were some things... well, there were areas where I just couldn't seem to talk to him."

"What do you mean?"

She played with the wrapper from her straw for a while as she formulated her answer.

"I know you'll find this a little odd for me to say, but I'm usually kind of shy. And that usually happens when I don't have a guy in my life. But, when I met Johnny, he was so... Well, we did things that... I mean, I'm... I'm... what you might call," she paused, then blurted, "I'm what you might call an 'adventurous' girl."