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"After that, she was ready for more. She quit her grocery store job and instead found several other guys similar to the first guy she met. Some were younger, some were older, but all of them were looking for the intimacy they weren't getting at home. Not just sex, but the intimacy that goes along with it. Kissing and caressing, talking, truly getting to know one another. Sharing thoughts and perspectives.
"By February she was making around $2,400 a month, more than enough to live comfortably and not have to worry about having a roommate. And instead of working 20-30 hours a week, including late night shifts in a dangerous part of town, she was spending 2-3 hours a week with one of her sugar daddies, either in nice hotels, at their houses, or at her place. She's got almost $5,000 in the bank and has even started contributing to a Roth IRA. All on her own."
I looked at him, incredulous, and said, "You're actually kind of proud of her, aren't you."
"As weird as it sounds, Jackie, yes. I am. She's helping these guys out, and in return they are helping her establish herself financially and helping her focus on her school, instead of her having to check groceries at 11 o'clock at night in a crappy part of town, just to earn minimum wage. And she did it on her own, for the most part, with almost no help from us."
"But... but... she's... she's having sex, for money... with... how many guys did you say she has?"
"Three up in Seattle, from what she's told me. And now the one guy down here in Palo Alto."
"Wow. So four guys. Plus Leo. And you. I don't... I don't know what to say."
We sat in silence for a few more minutes, as I thought about Jenna and her multiple partners. Some part of me recalled a time many years earlier where I had fucked 5 different guys (in addition to Rich) over the course of a long weekend. Rich had set it up as a sort of extended gang-bang. Had every guy shown up it would have been closer to eight different guys. And then there were my experiences with multiple men while on vacation in Mexico. And Tampa. And Houston. So was I really in any position to judge Jenna for what she was doing?
Eventually Rich spoke again, and said, "So now you see why me having sex with Jenna really isn't that big of a deal for her. Sex is something she enjoys, a lot. Like a lot. And she enjoys it with many, many people, especially people she cares about. She has developed friendships with all of the guys she sees, and it has given her a confidence that is genuine and strong. And as I said before, it's deepened my relationship with her already. I know it sounds weird, and kind of fucked up. But it is the truth, Jackie."
I didn't know what to say. My mind was once again racing, waves and currents of worry and fear pulling me in so many directions. Rich gave me a few moments and then said, "Come on. We're here. Let's go have a margarita and some good food. Hopefully that will take your mind off things."
We got out of the car and walked into the restaurant, which helped to distract my confused and conflicted brain. It wasn't busy, and thankfully our regular waitress saw us come in, so that when she arrived at our table, she already had two margaritas ready for us.
I took a big drink, followed by another, and then sat back, lost in my thoughts again. Rich tried to get my interest in what to order, but I ignored him, knowing he would order my usual dish. Instead, my thoughts were focused on the conversation in the car. Parts of it made more sense than others.
Had I really raised my daughter to be a prostitute? Where had that come from? I looked over at Rich, and asked, "Where did we go wrong, in raising Jenna? I still don't... don't understand why she would... do that kind of stuff."
"I don't think we did anything wrong. She's always been adventurous, curious, and goal-oriented. She's always wanted to do things on her own, be her own person. We taught her right and wrong, taught her about the way the world works, helped her become a mature, thinking person with a strong intellect and strong work ethic. You could say the same thing about Dylan and Mandy."
"But... to do that... for money? Doesn't she know that's... wrong?"
Rich shook his head, and said, "You can think of it like that, or you can try and see it from Jenna's point of view. To her, she's helping her friends with their needs, and they are compensating her for the time she spends with them. From what she's told me, it sounds like she has healthy relationships with all of them. They like helping her out and treat her with respect, and she has just as much fun as they do. I know you don't see it that way, but I have to admit, I don't blame her for what she's doing."
I shook my head, and said, "Ok... ok. You might be right. It's just... so unexpected. And you promise me, she's not out on the streets, dressed up like a hooker?"
"Definitely not. Although from the pictures she showed me, several of her clients enjoy seeing her in very expensive lingerie. And she looks amazing in it."
I drank the last of my margarita, and Rich asked, "You finished that off pretty fast... did you want another one or should we go straight to taking shots of tequila?"
I laughed and said, "I think it's probably best if I switch to water at this point."
He smiled at me, and our food arrived moments later. Rich took the conversation to other topics, providing further distractions for my mind to focus on, helping me relax and cope with what I had just learned about my daughter. I knew what he was doing, and loved him all the more for it. Such a sweet man I married.
The car ride home was much more enjoyable than the drive to the restaurant. We talked more about Jenna, as well as about how to be careful around Mandy and Dylan. Dylan would be home in about two weeks, and Mandy and Trevor lived close enough to us that there was a risk of them dropping in unannounced. I could just see one of them stopping by and catching Rich fucking Jenna on the dining room table. It made my head spin in both good and bad ways.
We got home and sat down on the love seat to watch some TV. I was about ready to head to bed when Jenna got home. She gave us a big smile and said hello, and came and sat down on the couch.
Rich asked, "So how was your date with Leo?"
"Ugh! Dad! It wasn't a date. We just hung out, that's all. It was fun. We made some dinner and watched a movie."
"Were his parents home?"
"No, they were out for the evening."
"So I'm guessing you did more than just watch a movie with him."
She grinned nervously and glanced at me, then said, "Maybe, but that's none of your business."
"It's ok... I hope you don't mind, but I told Mom about your... unique relationship with Leo."
I added, "It sounds like you guys are enjoying the time you have, before he leaves, later this summer?"
"That's right, yeah. It's nothing serious, I promise. We just... kinda have some fun, every now and then."
"He totally fucked your brains out tonight, didn't he."
"Dad! I can't believe you just said that!"
"Am I wrong?"
Jenna hesitated, glanced at me again, and then said, "No, I guess not, but..."
I said, "It's ok, Jenna, I'm totally ok with it, honest. I won't ask a bunch of questions or get all wound up. I promise."
She gave me a weak smile, and said, "Ok... thank you... I appreciate that."
Rich chimed in again, with, "So... can I have a look?"
Jenna blushed and said, "Right here? Right now?"
"We can go back to our bedroom, if you'd prefer?"
Jenna gave him a coy smile, then looked over at me, to gauge my reaction. I gave her a smile and said, "I'd be curious to have a look, too... and... a taste."
She blushed again and grinned, and we all got up and went back to our bedroom. Before I knew it, Rich had slipped out of his shirt and shorts and was completely naked, kneeling in front of Jenna. She pulled off her summer dress as he hooked his fingers under the waistband of her thong and slowly pulled them down. By now I was completely naked as well, and when I looked over I could see a white sticky mess filling the crotch of her thong.
"Wow!" Rich said as he took a look, then looked up at me. "Do you want to eat her first, or can I?"
I gave them both a smile and said, "Why don't you lay back and let Jenna suck you, while I get to enjoy cleaning her up."
Rich smiled wide and moved to the middle of the bed, laying back as he watched Jenna climb on and move over him, taking his already stiffening cock into her mouth. I got behind her and took a long look at her pussy. It was a sticky mess, smeared with cum. A lot of cum. I wondered if this was all just from Leo, or if she had stopped off to see her sugar daddy on the way home from Leo's house, and I was seeing his contribution as well.
I moved in, breathing in the intoxicating scent of sex, the heady mix of her sweet wetness with the pungent smell of the cum. I wasted no time and instead began to lick and suck her pussy, scooping out gobs of cum from deep inside her, feeling her body shiver and hearing her muted moans, her mouth wrapped around Rich's cock.
I just about had her cleaned up and was beginning to focus on her clit, causing her to moan louder, when Rich asked if we could switch places. He moved out from underneath Jenna and got behind her to fuck her, while I moved up and spread my legs, so that she could eat my very wet, swollen pussy. Her tongue felt amazing as she lapped up my wetness and pleasured my clit, my eyes locked on Rich as he pumped her steadily behind. We shared another long look, filled with lust and desire and pleasure.
A few minutes later, I could tell Jenna was ready to burst, and I didn't have long to wait. She lifted her head up, her eyes pleading with mine as Rich's cock continued to pleasure her pussy. She gasped loudly and then let out a long moan as her orgasm swept through her, causing her body to convulse several times. I didn't realize Rich was so close to cumming as well, and the next thing I saw was his head back, mouth open, gasping as he pumped a load of cum inside Jenna.
As soon as Rich slipped out of Jenna, he told her to move up and sit on my face, so I could enjoy another cream pie. Jenna smiled and did as she was told, placing her knees on either side of my head, lowering her freshly fucked pussy down onto my mouth. Rich's cum was already beginning to ooze out of her, and I licked and sucked up as much as I could, even though I knew some of it was smearing all over my face. I was already very aroused from Jenna eating me, so when Rich began to pleasure my clit with his tongue, it didn't take me long to have a brief, intense orgasm of my own.
Jenna laid down next to me, with Rich following suit a few moments later. We laid there enjoying the afterglow of our sex, closing our eyes and dozing off, sated for the time being. I lost track of time, and when I woke up, about 20 minutes had passed. I looked over and saw Jenna just starting to suck her father's cock, a coy smile on her face. I smiled back at her and moved in to help, licking the wetness off of his balls from our earlier round of sex.
Jenna stopped sucking his dick and asked if I wanted a turn, and I smiled again and began sucking him; and for the next few minutes, we took turns sucking on his cock, occasionally kissing each other, our tongues tasting the sex that was on our lips and in our mouths. On cue, Rich woke up and sat up, watching the two of us kiss and suck his cock until he was hard again.
He told Jenna to roll over, placing her back towards him. He scooted down, positioning his cock so that he could fuck her from behind, and had her spread her legs apart, her right leg under her, her left leg bent forward at the knee, allowing him to slide his cock into her and begin pumping her deep and hard. She turned to look at him, her mouth open, her breathing heavy, a look of pleasure and lust in her eyes that I knew Rich was sharing.
Rich moved his left hand around to the front of her pussy and began playing with her clit, causing Jenna to close her eyes and tilt her head back as she moaned loudly. Another orgasm washed over her, her moans becoming whimpers as Rich continued to fuck her deep for a few more moments.
I knew what he wanted, and so when I saw him slip out of Jenna, I rolled onto my left side, my back to him, my legs spread open, and felt him slide up behind me and guide his sopping wet cock into my pussy. I gasped loudly, as did he, and he began to fuck me hard and deep, picking up right where he had left off with Jenna, his right hand moving first to my breasts to pinch and caress my nipples, before moving down to finger my clit, eliciting another loud moan from me as the pleasure amplified.
From his ragged breathing and grunting I knew he was very close to cumming, but was holding off until he felt me begin to orgasm. A few moments later, I began to climax, a pulsating orgasm that overtook me and made me shake and cry out, Rich's moans mixing with mine as his cock spurted a load of thick cum inside of me.
Rich held himself in me, his arm over me, and I felt his body relax as he drifted back into sleep. I let myself drift off, and didn't wake up until several hours later. Jenna was gone, and she had thoughtfully pulled the comforter over us and turned off the lights. I settled back in next to Rich and fell asleep quickly.
Sunday morning came, and it wasn't until after 9am that I got up out of bed and threw on some clothes to go make coffee. I stood by the coffee maker, lost in thoughts -- erotic thoughts, worried thoughts, pleasurable thoughts, nervous thoughts. When was Dylan coming home again? What would happen then? And what if Mandy had come by last night when Jenna and Rich and I were...
I stopped myself. I couldn't allow all my worries and fears take over. Not right now. It was a beautiful morning. I had slept wonderfully and now had a hot cup of coffee in my hands. I curled up on the couch and enjoyed the quiet.
Jenna stumbled out about a half hour later, wearing just a tank top and a thong, and reached up into the cabinet to get a coffee mug, pouring out a cup for herself. I looked at her, admiring her lithe body, toned, tanned, supple. Her luxurious blond hair, accented by darker roots, cascading down her shoulders and back. Her perfectly perky little breasts, her curvy, firm ass. It dawned on me that I had enjoyed those breasts, and that my tongue had been inside of her, multiple times. I knew what she tasted like, knew what her tongue felt like on my clit, knew what her moans of pleasure sounded like, knew how her face twisted in exquisite pleasure as she came.
Without trying to, I realized I was comparing Jenna's body to Mandy's. They both were beautiful, and I briefly wondered what it would be like to be with Mandy -- and had to stop myself. I wasn't going to go there, in real life, much less in fantasy. Or at least I told myself that. The conflicted thoughts and feelings I had been having came rushing back. It took some time to work my way through them, but they eventually passed on.
Jenna came and sat next to me, mumbling a good morning as she laid her head up against my shoulder. I leaned over and kissed the top of her head, and asked how she slept.
"I slept good. Really good. Last night was... kinda kinky, kinda fun."
"Do you mean with Leo, or with your old Mom and Dad?"
She quietly laughed, and said, "Leo can't hold a candle compared to you guys. To be honest, he's not that good of a lover. It's a lot of just fucking, and most of the time he cums before I can even get going. With you and Dad... it's really good. Really erotic. You both make me cum really hard."
I smiled and said, "Well, I'm glad we're still good for something."
She laughed again and said, "Yes. Definitely."
We sat there in silence for a few moments, and then I said, "Jenna, I want to apologize... sometimes I get really worked up, and worry about things I can't control. I forget you're an independent woman and are mature and wise enough to make smart choices. I don't think I realized that fully until now. I'm sorry for driving you crazy with too many questions, and too much nagging. I'm going to try and be better, I promise."
She squeezed my arm, and said, "Thank you. I appreciate that. I know you love us all, very much."
"That is for sure. And I'm really enjoying being with you. It's definitely a side of you I didn't have a clue about! From what Dad has told me, it sounds like you definitely know what you like when it comes to sex, and have had some very interesting adventures."
She sat up, a puzzled look on her face, and said, "What do you mean? Oh... I get it... Dad told you about... my sugar daddies. Didn't he."
"Yes."
"Just 'yes'? Aren't you going to lecture me, or judge me for what I've been doing at college?"
"No. I'm not. It's none of my business."
"Really. I find that hard to believe."
"Ok, yes. I was upset when I heard about what you had been doing. But your Dad and I have talked through it all, and I see his logic -- your logic -- and I can't argue with it. In the end, my opinion doesn't really matter. You are your own woman. And to be quite honest with you, I have no room to judge, considering some of the things I've done over the years."
"Like what?"
I laughed softly, and said, "Oh, I could tell you stories. Sordid stories about some of the guys I met up with over the years. Lots of married guys, a few that were engaged or had a girlfriend. I got good at seducing men, and didn't always make the wisest choices."
"Does Dad know?"
"Oh yes. We've always been very open with each other about sex. He's had his fair share of flings and sexual relationships. Didn't he tell you about some of them?"
"He hinted at some of them, yes, but he didn't tell me any specifics."
"Well, maybe at some point in the future we can open up and share some of our past experiences with you. Some of it may shock you. You may not think very highly of us, after you heard some of it."
"Like what?"
"I'll give you one example, and then I want to go make breakfast. I'm really hungry!"
Jenna smiled, and looked at me expectantly.
I sighed and said, "Ok. So... many years ago, when you and Dylan and Mandy were in grade school and I was just getting started in real estate, I got to know a couple who were looking for a house. They were an odd match; he was older, in his mid-40's, she was in her 30's. His name was Phil, I can't remember his last name. They had two or three little kids at home, and she hadn't really taken care of herself and was on the bitchy side, overweight and generally unpleasant.
"I must have shown them at least five houses, if not six. I could tell the husband was attracted to me, and I found him somewhat attractive, as well. They eventually settled on a house, and I helped them through the entire process. I even bought them a really nice housewarming gift for them and took it over to their house.
"When I got there, he was alone. His wife had left shortly before I got there, to take their kids to the zoo. One thing led to another, and eventually we wound up fucking in their bed, several times. He actually had a rather large, thick dick. It was tough to suck but I really enjoyed riding him. Mindblowing orgasms.
"After that, I would occasionally check in on them, ostensibly to make sure they were happy with the house, but in reality to see when he might be free for some more fun. He fucked me in their bed probably four or five times, until one time when we had a very close call, as in, I'm driving away from his house as his wife turns onto the street where they lived.
"We decided to start meeting up at my house instead of his. Phil was worried your Dad might find out about him coming over, but I assured him I could keep it a secret. In reality, your Dad knew about all of this -- we never kept secrets from each other, and still don't. But I assured Phil that your Dad was clueless and would stay that way.