Sexual Bon Vivant Pt. 05

Story Info
Tragedy brings families together.
4k words
4.33
7.5k
7
0

Part 5 of the 7 part series

Updated 06/09/2023
Created 05/08/2018
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

"I did not even get your name. You know mine. I would really, really like to see you again (outside the store). Would you like to get coffee, or maybe even dinner some time. Here is my phone number. I do want you to call. I don't go in until mid afternoon most days.

Hope to see you soon,

Peggy (Margaret).

The note, written on fancy pink stationery, had been tucked away in my underwear drawer for almost three weeks. It was written by clerk at a department store; she had placed it in the bag with my purchase. She was a handsome mid 40's lady. During our brief conversation, I had let it slip that I preferred older women. I did not mention that I also liked older men. I figured the fact that I was buying panties might have been a clue.

I had taken the note out at least 20 times, but could not bring myself to call the number. I don't know what kept me from calling. Perhaps it was the fact that a brief fling with a dominating alpha male had taken up a lot of my time.

But this lady and her note had been beckoning me. I had had two previous flings with older women, one of which was a one time thing with my mother. The other was with the wife of an older man who had initiated me into male sex. I had the feeling this one would be very good in bed, The fact that she wrote that note lead me to believe that.

Part of the reason I hadn't called was the timing. I was sure she was expecting a quick reply and now a lot of time had passed. Was she angry? Or had she completely forgotten the slightly built college boy?

I paced around the apartment, trying to get the courage up to call the number. It had been a while since I had been with a woman and I missed it. And if I still wanted to think of myself as "bi" I would need to get back to the fairer sex.

I finally picked up the phone. The cord had become tangled, so I unraveled it while the dial tone hummed. I dialed the number. After what seemed like a hundred rings, an out-of-breath woman's voice came over the line.

"Hello? Hello?"

"Hi, you probably don't remember me. but I was the guy who bought the panties 'for my mother.' I..."

Oh hi, Betty, I see. Right now. Can't it wait? Oh Okay, meet you at the store in twenty minutes."

Now I was trying to figure out what was going on. "Peggy? what..."

"I said I would meet you at the store. Twenty minutes got it?"

"Okay, you want me to meet you there?"

'Yes," Then her voice was muffled, "It's Betty down at the store, I need to go." Then she whispered, "Be there!"

All I had time to do was change to a clean shirt and swish a little mouthwash. So what if she was married. That would just make it three for three.

*********

I did not want to linger around the women's intimates section so I circled around looking for Peggy to arrive. I was standing in the men's underwear department when I felt someone behind me. It was her, as pretty as I had remembered. Only her hair was down and she was much more casually dressed. She had on a floral print sundress and white canvass deck shoes, It looked as if she had hurried to get here. That was a good sign that she was eager to see me. Or maybe glad to get away from whoever she had at home. I started to ask a lot of questions, but she stopped me.

"Not here. There is a coffee shop across the parking lot, I'll meet you there."

On my way, I wondered about the wisdom of seeing another married woman. But then, wisdom was not my greatest attribute lately.

She was seated at a table in the back when I got there. She had a radiance about, like it was Christmas morning.

"Hi, I guess you are wondering about all the cloak and dagger stuff?"

"I'm guessing you are married or otherwise involved, and that you don't want anyone at work to know you are meeting someone half you age for...whatever it is."

"That is pretty close. So why did you stick around after the phone call?"

"I did tell you that I am attracted to older women, and you are the prettiest lady I have seen. I have no problem with you being married, It would seem that most mature women are. So, are you married?"

"Yes, but it's not a simple as that. But let's talk about you. How long have you been wearing women's panties?"

"What?"

"You heard me. And don't give me that bullshit about buying them for your mother."

"Okay they were for me. But that was the first time. Honest."

"Then why now? You are, what, 20? 22? I would think you would have indulged that fantasy years ago, maybe with Mom's panties, maybe a sister's. Of course, you are in college; that's a time to experiment!

"That's it, I was experimenting. I wanted to see how they feel."

"And how your cock looks in panties. Goodness knows I have been imagining how you look wearing them."

"Really? I was picturing how you looked in them, too."

"You have? I hope you didn't embellish too much. I would hate to disappoint."

"So you are saying I will get a chance to evaluate you?"

"No, maybe. That will depend on several things. My husband being the main factor. But not how you think.

"I'm not sure what to think, anymore, but I suppose I'm up for anything."

"Give me your number and I will call you. I have to go now. Wait for my call. I want to kiss you but this is not the place. Soon though."

She was gone in a flash. Leaving me with many more question than answers. But if it meant getting it on with this lovely lady, then I could wait.

******

Another week passed before I heard her voice on my answering machine.

"Hello, cutie. Sorry I didn't call you sooner. I had to get some things settled. Do you know the bar at the Riverside hotel? I will be there at about 7:00 Thursday. I really hope you can make it. Bye!"

This was interesting. Meet her at a hotel bar! Hell yes I'll be there.

The bright sunlight disappeared suddenly as I stepped through the door to the bar. I was blind momentarily until my eyes adjusted to the dim light. I could make out a handful of customers and I finally spotted Peggy. A scruffy old guy was talking to her, doubtless trying to pick her up. I made my way over to the other side of her. This allowed her to turn away from him. He continued talking to her until he realized she was not paying attention.

"I hope you choke on that drink I bought you," he said, walking off.

She smiled at me. "Sorry about that. I couldn't get rid of him."

"Glad I could help. I can certainly understand why he didn't want to leave. You look fantastic."

And she did. Her hair was pulled back, her make-up was a bit over done but sexy nevertheless. Her blouse showed a lot of cleavage and her short skirt highlighted her shapely legs. She balanced on impossibly high heels.

"Thanks. I was shooting for 'fantastic.'"

"I must say you always look great. How did you get out of your house looking this sexy? Your husband didn't notice?"

"I booked a room here and got ready there. As for my husband, would you believe it was his idea. He even picked out my outfit! Don't look, but that's him at the third table to your right."

I would say I was shocked, but compared to my recent exploits, this was almost mild. The first older lady I had fucked was by invitation of her husband. I casually turned my head. Her husband was an average guy, salty grey hair wearing a tropical print shirt. He was staring intently at us. From the empties in front of him, he had been drinking heavily.

I turned back to Peggy. She gave me a shy smile.

"He discovered swinger's magazines and bought one with local ads. He became obsessed with me having sex with another man. He has been pestering me to try it. I had no intention of doing it until you walked in the store. I knew I wanted you immediately, but I still needed to make it look good. We sent in an ad looking for a young guy. I got several replies and I told him I was meeting the one that I picked here."

"And he is here to, what?"

"He wanted to look out for me in case you were a psycho. Beyond that, we will just to see. He can stay here while we go up to the room, or he can go with us if you don't mind an audience."

"Let's just go to the room and see how that goes."

Peggy grabbed her purse and headed out, stopping briefly to say something to her husband. He gave me a serious look as I walked past his table. I simply nodded and kept following his wife's luscious ass out the door to the lobby and down a hallway to their room.

Once in the room Peggy transformed into a sex starved tigress. She told me she hadn't had sex with Henry, her husband in a couple of weeks in anticipation of today. I believed it. She wrapped me up in a hug and began planting deep passionate kisses on my lips, cheeks, and neck. When she came up for air, she began shedding her clothes starting with her blouse. As she peeled it over herded, I saw the sexy black bra that no doubt came from her store,

In response, I quickly unbuttoned my shirt, dropping it next to her top on the floor. We had another round of kisses This time I bent down to kiss her ample cleavage. I couldn't wait to see and taste her breasts so I reached around to unfasten her bra. She held the cups in place for a few seconds of false modesty before dropping it to the floor. I was at last able to see and feel her full tits.

Rather than stoop down for access, I eased her onto her back on the king bed. I caught a brief glimpse of he black panties as she pushed herself back. That gave me a better idea. She raised her hips as I reached under her skirt and hooked her panties. I pulled them off over her tall high heels. I then stuck my head under her skirt. It was a tight fit under there, but it was worth it as my mouth made contact with her sweet pussy.

The combination of my pussy eating and her two weeks of celibacy lead her to a quick and powerful orgasm.

"Fuck me, now. God, I need your dick."

I peeled my pants sown and her eyes lit up when she saw the bright red panties that she had sold to me. This was no time for a fashion show, so I stripped the lacy garment off. My cock is nothing to brag about, but Peggy looked at like it was a porn star's cock.

"I wanted to fuck the minute I saw you, Jonathon! Don't make me wait any more!"

I followed orders and lined up with her slick hole and drove forward, sliding smoothly into this incredible lady's most intimate place. The heat and moist friction was beyond anything I had ever experienced.

She was certainly enjoying herself as she had several smaller orgasms as I pumped in and out.

About then I heard a key rattling the door. I was afraid it was the hotel employees checking on the noise coming from the room. I started to pull out, but Peggy's legs were wrapped around me.

"Relax, I told Henry to give us a few minutes and to come on in."

By this time he was standing beside the bed. I could smell beer.

"She has a great little pussy, doesn't she, kid?"

"Henry, I told you you could watch, but you had to keep quiet! And his name is Jonathon, not 'kid.' You understand."

"Yes dear,"

He moved to sit down on a chair and we made eye contact. I could tell he was apprehensive but maybe excited as well.

With that interruption out of the way, and with Henry now watching her, Peggy was reinvigorated. She matched my thrusts, She then had me lay on my back while she mounted me cowgirl style. I assumed it was so she could see Henry's reaction, Henry was now naked himself and his hard-on betrayed his arousal.

"You like watching your faithful wife fucking other men? I can see that you do. You better like it because I like it and I'll keep doing it. Do you know how many men have asked me out since we have been married? Dozens. And I won't tell them no anymore. You would like that? Me going out and fucking strangers. I may bring them to our house and fuck them on our bed"

"Yes! With that he approached the bed to kiss her.

My head was now hanging just over the edge of the bed. As Henry kissed his naughty bride, his cock presented itself to my mouth at a perfect angle. Thinking, "why not," I opened wide and took his whole length.

He initially tried to pull back, but sighed and pushed in deeper.

Peggy did not immediately notice that her husband's cock was being deep throated. However his moans alerted her to the fact.

"Henry, I'm the one who is supposed to be getting another guy!"

"Ah...uhh...uh," was all he could say. I was sort of proud that I could render him speechless with my oral skills.

"Jonathon, I knew you were a pervert, I didn't know how much of one. Suck him good."

I intended to do just that! The fact of having my cock deep in Peggy's pussy while sucking her husband was a huge turn on. Apparently it had the same effect on them as well. Peggy yelled out with another orgasm which caused Henry to unload in my mouth. All of which sent me over the top. I shot several big blasts of my cum deep inside Peggy's grasping cunt.

Henry surprised Peggy once more by burying his face in her cum-filled pussy. I had a feeling they needed some alone time to sort things out in their relationship. I dressed and headed home. Now this was my kind of couple. I had a feeling it wouldn't the last time that I would spend time with them.

*********

In a couple of years, word of a new deadly virus had caused me to break off all sexual contact with men, I had graduated school and had moved out of the apartment I had shared with Steve.

As if that weren't enough change for me, my life was about to be rocked even harder.

After splitting with Steve, I moved back in with Mom and Dad to save a little money. Having fucked my Mom on that fateful night there had been some tension between us but that had eased a little with each holiday visit. I still felt ill at ease when all three of us were in the same room, but it was manageable. And I could not look at Mom and not see the naked body I had once ravished. I caught her staring at me as well. The subject of that night never came up.

She had said Dad had given her permission to see other men and I knew full well she was making use of that fact. She went out at least once a week, "with the girls." But my former lover, Carol, who also Mom's best friend knew of no such group.

"She hasn't told me, but I would guess she is getting fucked. And probably by some young guys. She likes them young!"

"Thanks, Carol. I really didn't need to hear that."

"Goodness knows that I like them young, too."

"So you and Frankie are still going strong, I take it."

"Yes."

"That's good. Well, nice talking to you."

"Ok Jon. Oh, are you going on the opening day deer hunt? Frank is going, but not Frankie, He says he just doesn't want to hunt anymore."

"I don't either, maybe he and I can get together this weekend. Maybe compare notes, you know, guy stuff."

"Ok I will let him know."

********

With Dad and my brother gone to hunt, Mom had the house to ourselves. I started to bring up the night in the hotel, but chickened out. Let sleeping dogs lie.

But that would soon change. We were expecting the hunters home after dark Sunday, Around midnight, Mom got the visit that no wife and mother wants to hear. Dad, my brother Sammy, Frank and two other hunters had died when a space heater had set fire to the hunting lodge.

It was a horrific event that hit us hard emotionally and financially. The same went for Carol and Frankie. Frankie had already been prepared to take over his dad's construction business. I hadn't yet found a permanent job but we subsisted on Mom's work and whatever odd jobs I could rustle up.

I got a call from Frankie after a few months, saying that though he took over the company he still needed someone to take his place doing sales calls. I immediately accepted. He said there was some other matters we added to discuss in person and he invited my Mom and I to a barbecue at their house Saturday as well. I accepted that also.

Mom was happy to go to a social event again. I think Carol's shared pain was the only reason for her to go.

Once there we had a good time. Good food and a pool helped in that regard. The swimsuits the moms wore certainly did. Both wore skimpier bikinis then thy might normally wear this soon after being widowed. Maybe this was coordinated since I doubt either one would have dared dress so provocatively alone. If the plan was to get us horny, then it worked.

Soon it was time for a talk. Frankie called us into the house. Is at between Mom and Carol on the large sofa where I had first seduced Carol. The cool inside air combined with the damp bikinis brought their nipples to poke prominently against the fabric.

Frankie started things off by stating the obvious; we were hurting financially. He pointed out that hiring me would help both our causes, but would it be enough?

"I want you to consider this: Sell your house and invest the money."

"Where would we live?"

"That's the beautiful part. You and Joan can move in with us! We have four bedrooms an plenty of space. Of course rent free. And don't forget the pool. That would be an excuse for these hot ladies to keep wearing bikinis.

We discussed the pros and cons for a couple of hours. We decided the pros won.

"Great, it's settled. Let's celebrate." Frankie had iced some champagne to celebrate. He made an effort to keep the ladies glasses full until they were giggly and beginning to slur their words. He stood to speak again.

"I suggest we make tonight your first night here." The moms giggled. He sat down next to Carol and pulled the strings holding up her top. Her nice tits jiggled free, They were as pretty as I remembered.

My mom was watching them.

"Mom, we haven't discussed that night."

"Jon, I have wanted you so much, but it would not have been right. Still isn't, really. But with your Dad... I guess if Carol thinks it been a proper mourning period, then I do, too." Carol apparently thought so since she was now naked riding Frankie's hard pole.

Mom leaned in and whispered, "don't worry we are both back on the pill, so give me a proper fucking."

"We?"

"Well, yes. Carol and I planned this. The best part was filling my prescription. The pharmacist knew your Dad so I'm sure that it got his attention. Now I just need your attention!"

I leaned across her body to kiss her. I ran my hand down her belly then slid it under her bikini bottom. Her lips spread for my probing fingers. Three went in smoothly. As I gently stroked her slick canal she threw her head back moaning loudly. I ripped her bikini top down exposing her breasts. Frankie, who was now pounding his mother's pussy missionary, had a perfect view of my mom's tits.

Mom lifted her ass and peeled her bikini bottoms down. I flipped her onto all fours and settled in behind her. I stopped to enjoy the view of Mom's ass and Carol's jiggling breasts. In this position it would have been very easy for her to lean a little and take one of Carol's boobs. I wondered if anything had ever gone on between these two friends. That thought made my already hard cock even harder if that was possible. I aimed at her swollen pussy and filled it up.

The whole situation was surreal. Two friends fucking their mothers like they were cheap hookers. I guessed that all of us had been celibate since the tragedy. I know that I had been and I was sure Mom had.

Her pussy was as hot as a furnace. I got into a rhythm. I knew that I wouldn't last too long. But I lasted long enough to bring a screaming orgasm. That triggered my own climax, flooding her womb with my seed.

Mom and I stayed in the same bedroom that night, making love once more. However in the morning I woke to a naked Carol sucking my dick back to life. Since Mom was nowhere to be seen, I could only assume she was with Frankie. I assumed correctly.

"Wait for us!" It was my mom with an aroused Frankie. Both were naked.

"Come in, Joan," said Carol."We have room."

12