The Personal Ads

It was the late 1980s. No internet, no craigslist, no online dating. Looking to satisfy a craving, I entered the world of newspaper print personal ads. These "sex wanted" ads would usually be in the back of the local alternative news & arts weekly papers. Newspapers with titles like "The Village Voice", or "The Reader". In fact, Hollywood made a good but now forgotten film about it simply titled "The Personals".

"Wanted W4M

Are you an older mature woman who desires a younger man?

I prefer ages 50+, I'm in my 30s

All serious inquires will get a reply

Box # 334216"

With the ad submitted via postal mail, there was nothing to do but wait for publishing and (hopefully) replies. The local paper would receive the replies, put them into an envelope and mail them to the ad poster about once a week.

Fast forward 2 weeks.

The first batch of replies finally arrives. 6 or 7 total. Not bad.

Most of the replies were average and similar to each other. One was from someone that apparently didn't read my ad (just like craigslist today, some things never change). And then there was one that jumped out at me....

"Dear 334216,

You ad caught my eye immediately.

I'm an older woman who needs to be with a younger man.

Maybe you.

Please write.

Remember, fantasies can be fun!"

FANTASIES CAN BE FUN!..........WOW!

I wrote back and then took her short letter to bed with me and read it over and over while holding it up with one hand. It didn't take much to get totally turned on back then. Porn in the 80s was limited to magazines at the dirty book stores, peep shows, rental video tapes, and more mainstream publications like Playboy and Penthouse.

I heard from Fran a few days later. This time is was a 2 page letter...

"...I long to be with someone as young as you again. It has been too long for me. I hope we can meet soon, and I really hope that we hit it off. Remember, fantasies can be fun!"

Again, she wrote "fantasies can be fun!" My imagination went wild.

We set a date to meet. It would be at the Arts Museum. Her name was Fran. She described herself as 64 years old, somewhat heavy but curvy, with shorter gray hair.

I arrived early and stood outside near the main entrance. I looked around over and over, no Fran. It must have been 20 minutes, and then suddenly, almost from out of nowhere, a woman matching her description came walking up the steps, wearing a hat, with her head down. Was it her? Is she shy? Embarrassed?

I walked toward her and said, "Hi, um, Fran?"

"Yes. Hi, I'm Fran."

"Hi Fran, I'm Jonathan. It's nice to meet you!"

"It's nice to meet you too," replied Fran.

"I'm really glad you replied to my ad!" I said.

Fran replied, "I wasn't sure at first, but then.....well, now I'm glad I did."

"Me too." I continued on, "Would you like to go inside and see some of the exhibits and talk a little?"

"That sound nice, Jonathan. Lead the way."

Walking around the museum, I'm not sure either one of us was really looking at any of the exhibits. It almost felt like a nervous teenage first date. As we continued to stroll about, Fran made the first move and wrapped her arm around mine and pulled me in closer to her. I gave her a gentle pull back and thought to myself, "everything is going to be okay."

We walked about some more, arm in arm, when she turned to me and said, "The museum is nice, but maybe we could go somewhere more private?"

"Would you like to go to my place, Fran? I have a nice, modern apartment not far from here."

"Okay," Fran replied, "I took the bus here, do you have a car?"

"It's parked just outside."

We headed out of the museum and drove over to my place.

"Looks like a nice place, good neighborhood." Fran said.

"I like it. It's quiet, but close enough to everything."

She took my hand as we entered the lobby and headed down the hall.

"Well, this is my place Fran. Come on in."

She looked around a bit and then we both sat down on the couch. We were quiet for an uncomfortable moment or two, like we had both forgotten how to speak.

"It's really...," we both started to say at the same time, then we both laughed.

"I'll go first, I'm really glad to be here....and you seem really nice Jonathan."

"I'm glad you're here too Fran. I really liked your letter."

"You did? I'm pleased."

I took her hands in mine and asked "Would you like to read it together?"

Fran said, "That would be lovely."

I took her letter out of the drawer in the end table and said to her, "Come closer, let's enjoy this together."

I read out most of it to her, with her reading next it next to me. Then, turning to her, I said, "I especially liked the last sentence." I looked at the letter again and slowly read to her "Fantasies can be fun."

"Fran, I can't tell you how, forgive me, how turned on I got when I read that last sentence."

"I'm glad you noticed, and I gotta admit, I was hoping to catch your attention with that."

"I like fantasies too, Fran. I have a lot of ideas in my head."

"Bedroom ideas?" Fran dared.

"Yes, especially bedroom ideas."

"You're ad, Jonathan, well, with the age differences and you looking for a much older woman and all, well....it does kind of suggest a few things in particular."

"Yes, it does, it was meant too. I have some ideas, really kind of personal secret ideas."

Fran replied, "I have some really private personal ideas too."

"I like you Fran."

"I like you too Jonathan."

We gave each other's hands a warm squeeze.

"I share with you if you share with me, kind of like I'll show you mine if you show me yours." I said.

Fran giggled, "I like the way you think."

"Okay then. How about you write your idea down, but hide it from me Fran. I'll tell you mine, and then you can show me yours.....I mean what you wrote."

"You're on."

"Well I guess it's me first." I said softly. "I'm kind of embarrassed."

"Don't be embarrassed Jonathan, I'm here now, just the two of us alone, and I suspect I'm thinking a lot like you. So, go ahead and tell me what you're thinking sweetheart."

"Okay, let me whisper it in your ear." I put my arm around Fran and pulled her ear to my mouth and whispered, "I have a mother and son fantasy idea."

Fran looked up slowly and a smile came across her face. Without saying a word, she unfolded the small piece of paper she wrote on and handed it to me. On it was written.....

"Mother and Son fantasy"

We both exhaled loudly, an exhale of relief. We turned to each other and kissed for the first time.

"Jonathan, I was so hoping, this is going to be so good."

"Fran, you are just perfect for me. I love the way you look. So, what is next?"

"I have an idea Jonathan, how about we relate to each other as mother and son whenever we are together, no more Fran and Jonathan, just me pretending to be your mommy and you pretending to be my son. I think it is called role playing. We can both feel free to get into character and speak to each other in our play roles."

"That sounds wonderful. I'm ready Fran, I mean....um.....Mom.

"I'm ready too...Son."

"Mom, we have always been close, but now I'm having, well, feelings for you. I mean, naughty feelings."

"Son, I love you, and it is okay. A lot of people have, well, feelings for each other. Sometimes they are naughty."

"Mom, I just want to kiss you."

"You know you can kiss Mommy anytime you want too. I like your kisses."

I leaned forward and kissed Mommy, but softer and longer than anything could be considered appropriate.

"Son, Mommy's blushing. I didn't expect.....but I liked it. You can do it again if you want."

I kissed Mom again, only this time a bit harder. All of a sudden Mommy slipped her tongue into my mouth and gently explored my tongue.

"I love you Son."

"I love you Mommy."

"Son, do you remember when you were very young and I breastfed you? I have a secret. Every time I fed you, it felt so good I had an orgasm. I'm dry now, but would you like to try it again?"

"Oh yes Mommy."

"Okay then," Mom said. "But if you are going to see me like that, I need to see you too."

Mommy stood up and unbuttoned her blouse exposing her large rounded sagging breasts. Her nipples hung on the bottom of each breast protruding out almost an inch.

"Son, it's your turn now. Take off your pants."

I stood up and loosened my belt, unzipped and slowly pulled my pants and underwear down. My cock sprang out toward my Mom.

"Son, your pee-pee so beautiful, and big. Now, lay your head down in my lap so I can breastfeed you."

I laid down under Mommy's beautiful and heavy breasts. She guided her right breast to my mouth and at the same time found my pee-pee with her left hand and started to lovingly squeeze it.

"Drink all of Mommy's milk, child. Mommy loves you."

I started to suck on Mom's erect nipple and she let out several moans. She stroked my head and hair with her right hand and continued to squeeze my cock with her left hand. There my cock was, with my Mom's hand around it, standing straight up, at least 8 inches.

I grabbed Mommy breast with both hands and tried to suck all of it into my mouth. Mommy tilted her head back and let out a hugh sigh.

She said, "That's a good start, but there is more we need to do. What we are doing together is called incest, Son. It is wrong by just about any measure on the planet.....and it feels incredibly good. So, if we are going to 'love' each other in this special way, we need to balance it with punishment for our sin, or we will go crazy. I'm going to stand up now, and I want you to do exactly what I say."

"Yes Mommy."

Mommy stood up and took off her pants, revealing a heavy patch of dark and thick pubic hair. She then spread her legs, placed her hands behind her head and said to me, "Son I want you to punish me for what I did with you, and for what I plan to do next."

"Punish you? How Mommy?"

"I want you to take the open palm of your hand and spank Mommy's pussy."

"Um, okay Mommy. I love you."

"Then go ahead, Mommy says it's okay."

I put my hand between Mommy's legs and slapped upwards, making contact with her hairy pussy area.

"Ummmm. Good. Again."

Slap

"Again, harder."

Slap!

"Yes. Again. Even harder!"

SLAP!

Mom let out a yell and panted, "Dear God, yes."

"Okay Son, now it is your turn. You're a sinner too. Stand facing me and take your hands away from your cock."

"Yes Mommy."

"Are you ready?" asked Mom.

"Ready for what?" I asked.

"You'll see."

With that she started to slap the sides and underside of my erect cock, lightly at first, the harder and harder. Eventually it hurt enough that tears came to my eyes.

"Are you okay," Mommy asked.

"I'm okay. It really hurt, but felt good all at the same time."

"Like I said Son, we needed to receive punishment if we are going to do things together."

Mom then said, "What we are going to do next will be pleasure for you and punishment for me, but don't worry, I'm okay with it, in fact, I need it. Let's go into your bedroom."

I took Mom's hand and led her to the bedroom.

"Son, pull back the sheets."

"Yes Mom."

"Son, I'm going to get on my hands and knees now, on the bed, and I want you to love me anally."

Mommy crawled onto the bed facing away from me, got on her knees, and reached back with both of her hands and pulled her butt cheeks wide apart.

"Son, I want you to take your tongue and lick Mommy's butt hole. It is a really naughty and dirty kind of sex, that is why we needed the punishment first."

I did as I was told and moved my face close to Mommy's butt. I grabbed each butt cheek with my hands so Mommy could use her hands to support herself, and I started licking. It didn't taste good, or bad. Not much taste at all. But to hear the way Mommy was moaning it was doing something. I started to lick harder and harder, trying to pull her asshole open with my hand and, I don't know why, but I wanted to stick my tongue into Mommy's asshole as far as it could go. Mommy was panting really hard by now and suddenly she stiffened up and let out a loud yell, "YES!!!!!!"

Mommy turned over, grabbed me, and pulled me on top of her in a bear hug and said, "Dear Son, that was so hot. I love you so much. Now I need to do something for you, something special. I want you to take that beautiful, huge, red hot cock and fuck mommy IN THE ASS!"

Mommy got back on her hands and knees and not another word needed to be said. I think we both understood we were about to physically bond in one of the dirtiest, most taboo, and almost downright sick forms of incest imaginable. Yes, I was about to butt fuck my own mother.

I got behind Mom, my cock was rock hard, pre-cum dripping out of it, and it felt like it was one-thousand degrees hot. I placed the huge mushroom head of my cock against Mom's butt hole opening and, with one slow thrust, inserted all 8 inches deep inside of her body. Mommy let out a scream and tears flowed down her cheeks.

"Mom, you're crying."

"It's okay Son, it's tears of joy. Now, FUCK ME please. FUCK your Mommy in her ASS!"

With that I started to move my cock in and out, watching it appear and disappear into my Mommy's anus. Mom started to moan with each stroke and I started to breath heavier and heavier. With Mommy's encouragement, I started to fuck her faster and harder, adding more power and length to each stroke. Her arms were trembling. Her heavy, sagging breasts were slapping her stomach and then her face with each thrust.

Mom then said, "It's time, go for it son. Mommy wants this more than anything in the world."

I pulled my throbbing cock all way back and then, with all the force I could muster, slammed it back into her as deep as it could go.

Mommy screamed, "DEAR GOD! FUCK! FUCK! OH MY GOD! FUCK ME! FUCK ME! DEAR GOD!"

I let out a blood piercing yell and my cock exploded shooting wave after wave of white hot cum deep into her body.

I laid on top of her with my still spasming cock inside of her. We were both drenched with hot smelly sweat, in fact her hair was soaked. I reached around her from behind and clamped myself onto her. We both fell to our sides together and laid there motionless forever.

I asked Mommy, "Is this heaven?"

Mommy said, "I think it must be."