Old Man’s Sex Advertisement



What’s your gender? Woman
How old are you? 23
What’s your race/ethnicity? White / Caucasian
What continent do you live on? Australia
What country and/or city do you live in? Melbourne
Highest education received: High school diploma
What’s your occupation? Waitress
What’s your current relationship status? Single
Religious affiliation: Agnostic
How religious are you? Not at all
What’s your sexual orientation? Heterosexual
How many sexual partners have you had in your life (including oral sex)? 7
How many hookup stories have you here posted before? 0

Old Man’s Sex Advertisement

How long ago did this hookup happen? 2 months ago

What was your relationship status at the time? Single

How would you best classify this hookup? One-night stand

How long did you know the person before this hookup? Just met that day

Tell us about your PARTNER(S). What did they look like? How well did you know them, had you hooked up before? How/Where did you meet them? How did you feel about them before the hookup? My hook up was with Stewart, a 72 year old man. Stewart turned out to be a rather large man, quite over weight with a big belly. He was about 5’11” tall with a “round” body shape. He was bald but had a big moustache and his chest and back were very hairy. His face was wrinkled and he looked a lot like the types of old men that were in the porn videos I had been watching.

How/where did the hookup BEGIN? What led to it? Was planning involved? Who instigated it? I had been at home alone, bored and watching porn. For the past 6 months I had been watching a lot of porn that featured dirty, fat, ugly old men and younger women. The videos really turned me on. After watching a few of my favourite videos I began browsing other sites and came across Craigslist. I noticed a post from a man who said he was 72 years old and wanted to hook up with a “naughty girl”. Impulsively, I sent a reply to the advertisement. While I immediately had a feeling of regret, I got a response almost immediately. He said his name was Stewart and a widower. He said he had not had sex for over 6 years. Anyway, I was intrigued and turned on by how naughty it seemed. I wasn’t sure about whether I could actually go through with having sex with a man that age, but I agreed to go to his home and give him a blowjob.

What happened DURING the hookup? What sexual behaviors took place (e.g., oral, vaginal, anal, kinky stuff)? How did you feel during it? How did they behave toward you? Were they a good lover? What did you talk about? How did it end? When I arrived at Stewart’s home I was very nervous. We had exchanged a few emails in response to his Craigslist post and he had asked me to wear something sexy for him. I had worn a long summer dress that buttoned down the front as I have traveled to his home. Underneath I had on a black lace bra and panties set, with black stockings and suspenders.

Stewart was quick to get things started, possibly because he was so horny but also because he may have sensed how nervous I was. He had been wearing a bathrobe when he answered his front door. As soon as I walked inside he undid the belt and I could see how hairy and fat he was. I could also see his wrinkly old cock – limp at the time. He walked over to me and began to unbutton my dress.

As he slid the dress off my shoulders, he looked me up and down. “Mmmmm…. oh god, you are stunning.”

He went and sat down in an armchair. “My wife never liked oral sex. Would you please give me a blowjob?”

I was so nervous but I knelt down on the floor in front of him. I looked up at him and saw him looking at me so eagerly. I was turned on by the way he hungrily started at my body. I bent down and tentatively licked his hairy old balls. He groaned and I immediately thought about the porn videos I spent hours watching. I started to feel a bit excited as I kissed and licked his balls some more.

As his wrinkly, old cock began to twitch and swell, I started running my tongue up and down it. He was beginning to get hard and I was relieved that at his age he could still get a hard on. His cock was very salty and his fat belly hung over it. I circled the head with my tongue and he moaned and groaned.

I began to slide my lips down around his cock and suck on him. “Ohhhh….fuck…. so good.” I heard him say. I continued sucking up and down his cock, feeling turned on by the idea that I was getting this fat, ugly, old man off. After only a few minutes, he begged me to stop, saying that I was going to make him cum too quickly.

The original plan had been for me to just give him a blowjob but he was now asking if I would let him touch me. He said he just wanted to lay on the bed with me and feel my tits. I had told him I did not want to have sex with him and he promised he would just fondle my boobs.

We went into the bedroom and I lay down on the bed. Stewart lay down beside me, his big belly looking like a huge white, hairy mountain. He reached a hand over and began to caress my breasts over the top of my bra. I had to admit that it felt good. “Please let me take your bra off.” Stewart was such a polite old man.

“OK” I replied and turned away from him so he could unhook the back of my bra. As I rolled back I saw the excited twinkle in Stewart’s eyes as he reached out and took my nipple between his fingers. He lifted himself up on on arm and slowly put his head down to lick my hard nipples. As I moaned he began to suck on my tits, his arm caressing my stomach and my arms. He was so gently and I was really turned on by the idea of this 72 year old man sucking on my 23 year old tits. “Do you like that?” he asked.

“Mmm.. yes.” I answered breathlessly.

“Call me grandpa.” I tensed. That seemed a bit weird but I liked the feel of his old lips on my nipples so thought it would be harmless to go along with it.”

“I like it grandpa.”

While stroking my arms, Stewart began to gently lift my arms above my head as he continued to lick and suck on my hard, pert nipples. Suddenly I felt something could touch my wrist. I had not noticed when we entered the bedroom, but I now realised there was a pair of handcuffs attached to the bedhead. He snapped them shut around my wrists as I looked stunned at him. “Don’t worry, grandpa won’t hurt you.”

I didn’t really know what to do. I was feeling uneasy but at the same time I felt this tingling of excitement. Stewart began to suck hungrily on my nipples and I couldn’t help but moan with pleasure. His had slide down my stomach and he began to slide my panties off. At the same time he gently rubbed his teeth on either side of my nipple, softly bitting it and then sucking and licking it as my back arched.

Stewart started to put his hand between my legs but I tried to hold them together. He began to try and spread them apart and while I still wasn’t sure about this experience, I was excited enough not to really resist. He shuffled down the bed and began to kiss my outer pussy lips. As he used his had to spread them apart, his tongue began to flick lightly over my clit.

Stewart then pushed my legs wide apart and pushed one of his wrinkly, calloused old fingers inside me. “mmm… so tight.” He began to push his finger in and out of my pussy; he could see I was wet with excitement. I was turned on by this fat, ugly, old man fingering me. After a little while he put a second finger inside and and finally he squeezed three fingers into my pussy. He was pushing them in to me hard and fast and when I looked at him his eyes were fixed on the site of his fingers in my young pussy. Stewart had a crazed look on his face. He was mumbling about grandpa finger fucking his girl, in between licking my clit.

It was when Stewart stood up and stopped finger fucking me that I realised I had been really getting off on this. He walked over to a set of draws on the other side of his bedroom and I wondered why he had stopped. He opened the top draw and I saw him take out a dildo. He was carrying it back towards the bed and I could see it was shaped like a penis and was black with a red cap at the bottom. Stewart began to twist the base and I could hear the vibration start.

Stewart knelt down at the foot of the bed, spread my legs apart and started to slowly insert the dildo inside of me. I was wriggling and struggling against the handcuffs, not sure if I really wanted this, but turned on enough not to scream out or verbally protest.

I could hear Stewart panting and groaning as he watched the dildo move in and out of my young pussy. I could tell he was really getting off on this as he pushed it in and out of me. He used on hand to push my left leg up and to the side so he could get a good look, while the other hand gripped the dildo as he pushed it in and out. His breathing was getting faster as he also began to fuck me harder and faster with the dildo.

When Stewart had been licking my clit I was almost ready to cum but it was clear to me now that his only focus was his own pleasure. After about 5 minutes or so of fucking me with the black dildo, he pushed it deep inside me, my young pussy clamping around it. This time he did not withdraw it, instead leaving it vibrating inside of me.

Steward slowly climbed back onto the bed, heaving his large, hairy body over my chest and kneeling on either side of my handcuffed arms. As he straddled me, he gripped his cock and shoving it into my mouth, said, “Suck it bitch… suck grandpa’s cock.”

The dildo was twitching inside my pussy as Stewart lifted his belly up over my head so he could get his old cock deeper into my mouth. He was pushing his cock into my mouth, calling me names and bellowing at me to suck him. It was easily the dirties sex I had ever had and I was so excited by it. I sucked his cock. I could see his fat, hairy belly above me as he pushed his cock into my mouth.

For a man of 72, I had not expected Stewart to be so forceful. But I was turned on by what a dirty, horny old man he was. His cock was thick and although it was a bit spongy it was harder than I had expected. He continued to fuck my mouth until I heard him groan out so loud. He thrust into my mouth once more and I felt a squirt of warmth and tasted the salty cum erupt down my throat. He kept his cock in my mouth as I sucked and swallowed.

When he finished, he climbed off me, removed the dildo from my pussy and undid the handcuffs. Stewart let me know that I was not expected to stay.

It was a dirty, nasty scene with an ugly, horny old man. I am sure all my friends would be disgusted but it was just like the porn movies I had been watching and it was hot. Stewart has emailed me to ask me to go back again but I am not sure yet whether I will hook up with him again.

How sexually satisfying was this hookup? Somewhat

Did you have an orgasm? No, but I was close

Did your partner have an orgasm? Yes, one

What happened AFTER the hookup? How did you feel about it the next day? What are/were your expectations/hopes for the future with this person? How do you feel about them now? I left almost as soon as it was over. I have mixed feelings about it. I know that I was really turned on by it. But I do feel ashamed of watching old man porn and I also feel ashamed and shocked that I was so turned on by such a disgusting old man. I would never tell anyone I know but I do think about it often and it make me wet to think about it. Stewart has asked for me to go back but I have not decided yet whether I will hook up with him again.

What precautions did you take to prevent STIs and pregnancy? (Check all that apply) None

What were your motives for this hookup? Fun, pleasure, horniness, Learning new things, experimenting

How intoxicated were you? Small amount of alcohol or drugs, not enough to feel it

What substances did you consume? Alcohol

How intoxicated was your partner? Small amount of alcohol or drugs, not enough to feel it

What substances did your partner(s) consume? Alcohol

How wanted was this hookup for you at the time? Somewhat

Did you consent to this hookup at the time? I consented to the original meet but things changed and I went along with it

How wanted was this hookup for your partner at the time? Very

Did your partner(s) consent to this hookup? They gave enthusiastic consent

To whom did you talk about the hookup? How did they react? No one

How would you best summarize people’s reactions about this hookup? I didn’t tell anyone

Did you get emotionally hurt as a result of this hookup? I don’t know / I’m not sure

Did your partner get emotionally hurt as a result of this hookup? Not at all

Do you regret this hookup? A little bit

Why do you regret this hookup? I am confused because I was so turned on by hooking up with this disgusting, fat, hairy, old man.

What was the BEST thing about this hookup? It made me feel so sexy

What was the WORST thing about this hookup? That I am ashamed to tell anyone about it

Has this hookup changed the way you think about casual sex, sexuality, or yourself in general? Yes. I still watch porn of old men and young women and had thought about hooking up with other older men as I did find it a real turn on.

All things considered, how POSITIVE was this experience? Fairly positive

All things considered, how NEGATIVE was this experience? A little negative

You have a hookup story to share? Submit it here!