When I was 34, I dated a 40 year old Puerto Rican woman I met through work. Getting alone time with her proved difficult, though, as she had three kids who, understandably, took up most of her time. When we did manage to have sex, it was epic – she had a body very much like Jennifer Lopez, so needless to say my mind fantasized a lot while we fucked!
Sometimes we would go weeks without having sex, and this really bothered me. I didn’t want to be the guy who complained about it because her kids were definitely more important but masturbating alone at home just wasn’t satisfying enough. I wanted that physical contact with someone. One night, after almost three weeks with no sex, I turned to “Old Faithful” – the Quest chatline, hoping to at least have phone sex with someone. I’d had moderate success with Quest previously – a few threesomes, a few fucks with strangers, and a few hot phone sex sessions with single women and couples. On this occasion, in 2013, I was about to get lucky again.
It was a hot summer’s night, and I was laying in bed with the ceiling fan on and the covers pushed away. The a/c was on but it was still hot. I was, of course, naked, but had only half-heartedly been masturbating. I had hit up the few girls I kept on call as my reserve fuck buddies – Jenna, a tall girl who I used to work with and who I fucked every few months; Brandy, a single mother who was a bit of a crazy chick but who was also tight as hell and willing to do anything; Beverly, a nurse who I had a fling with and had recently reconnected with after 7 years; and Donna, a middle eastern girl who I’d previously dated but who cheated (we stayed fuck buddies but decided a relationship was a no go area for us). Unfortunately, Jenna was out of town, Brandy had both her kids with her, Beverly was a travel nurse and was in California, and Donna didn’t answer (she was probably either drunk or fucking her boyfriend). My Puerto Rican girlfriend was, as usual, unable to get a babysitter. Frustrated, I dialled Quest.
I probably browsed the ads on there for 30 minutes or so, and I remember having to top up my minutes – $49.99 for about 200 minutes! I sent a few messages, received a few responses, but most of the conversations seemed to fizzle out. There seemed to be very few girls available in my area.
Just as I was about to hang up, I heard an ad from a women who said she was looking to chat, drink, and “maybe get together with the right person”. Taking a chance, I decided to send her a message, saying I was a 34 year old male and was looking for some fun. I waited to get confirmation that the message was delivered, and waited for a response. Several minutes passed, and I was about to give up, when I got a message back.
“Hi,” it said. “I like your greeting and would love to talk. What you looking for?”
I’d always found that being honest and direct helped avoid needless back and forth messaging with people who weren’t interested in fucking, so my response was simple: “I’m feeling horny, haven’t had sex in a while, and I’m looking for someone to fool around with.”
Laying back again, I waited for her to respond, but not expecting anything.
“Sounds good to me. How old are you?” came the reply several moments later.
“I’m 34,” I responded. “Would you like to connect live?” With that, I ***********ed option number 1 which would let her know I wanted to talk live. I waited.
“You are now being connected,” said the chatline.
“Hi,” I said, “How are you?”
“Oh hey, I’m good, how are you?” came the response.
“I’m good. What’s your name?”
“I’m Cathy, who are you?”
“Steve,” I said. “What are you looking for?
“Oh, just someone to hang out with, I guess,” said Cathy. “What about you?”
“To be honest, I’m really horny,” I said. “I’m looking to get laid.”
Cathy chuckled. “Really?” she asked. “And you’re 34?”
“Yes,” I said.
“Well, I’m 55, I’m a widow, and I’m overweight,” she said. “I think you’re a little too young for me.”
“I don’t care about age,” I said. “I honestly just want to get fucked.”
Cathy paused. “Well, I guess that would be ok. I’ve not been with anyone in a while.”
My heart started pounding. This was a good development! Anonymous sex with strangers has always been one of my biggest turn on’s and fantasies.
“Are you free tonight?” I asked.
“Wow, slow down there, tiger,” chuckled Cathy. “Tell you what. You can come to my place, and we can talk. I’m not guaranteeing any sex or anything beyond talking, but I’ll consider it after we meet, ok?”
I quickly agreed. We exchanged phone numbers, and Cathy soon texted me her address. It was in North GA, about 15 miles from where I lived. I quickly jumped in the shower, brushed my teeth, put on some clean clothes, and ran out the door. It was so hot I was sweating again by the time I got the a/c going in the car. I looked at the time – 11:25pm. The roads were quiet, very little traffic, even on I-75 south, so I made the trip in no time at all.
Pulling into a quiet cul-de-sac in Rossville, GA, I quickly saw Cathy’s house as described – white mailbox, red Ford Escape parked in the driveway. Sure enough, I saw Cathy sitting smoking on her porch, as agreed. I pulled in behind her SUV, turned off the engine, and got out.
“Hey,” I said.
She smiled and put out her cigarette. “Hey, glad you’re here! Let’s go inside where it’s cooler.”
She led me into her house. Decent size, decent little suburb, open plan living and dining area. No upstairs, everything was on one level. She sat on the sofa and gestured for me to sit on the chair opposite.
“So, your name is Steve?” she asked.
“It is,” I replied.
“Yeah, right,” she said. “No one gives their proper name on the chatline.” She winked at me. “But Steve it is!”
I grinned stupidly back at her. My heart was beating fast – I loved the thrill of anticipation. I looked her up and down – she was definitely what I’d call a BBW, very pretty in the face, greying hair cut short, but she wasn’t disgustingly fat, just a thicker older woman. She clearly took pride in her appearance and she seemed to smell nice.
“I see you, eyeing me up!” she said. “You’re a horny little fuck, aren’t you?”
I wasn’t sure if she was having fun or trying to ridicule me, but I didn’t really care. “I am, and I told you I was looking to fuck,” I said.
“You clean?” she asked.
“Yes. I work in healthcare and get tested fairly routinely because of the nature of my work,” I replied.
She hesitated, seeming to weigh up the situation in her mind. She reached for a glass of wine on her end table and took a swig.
“Ok. It’s been a hot minute for me as well, so looks like you get lucky tonight!” With that she got up and headed towards the hallway, before stopping, reaching for me and saying, “Come on then!”
I jumped up immediately and followed her down the hallway and into her bedroom, which was at the back of the house. She had a lamp on in there that she was able to dim down to a faint glow. The room was tidy, a large king size bed in the middle, and windows on two of the walls. A large dresser with a huge mirror stood opposite the bed.
Cathy got on top of her bed, leaned on one arm on her side, and said, “Take your clothes off, Steve.” She emphasized the word “Steve”, clearly still thinking it wasn’t my real name.
This is hot, I remember thinking to myself. Stripping in front of a complete stranger, a woman who was 21 years older than me, and who was willing to fuck!
I lifted my shirt over my head, bearing my chest. I slipped off my shoes and socks, then undid the belt and unfastened my jeans, before sliding them down to the floor. Shaking them off, I stood in front of Cathy in just my boxer briefs, my cock already hardening.
“Oh, you’re a good-looking boy, aren’t you?” said Cathy. “Very sexy young man.” I thanked her – I didn’t really work out, so I wasn’t exactly athletic, but I didn’t yet have a “dad bod” and looked fairly fit and strong.
“Why don’t you slip off that underwear and get up here on the bed?” she asked.
I was happy to oblige. The underwear slipped to the floor and I stepped out of it, fully naked now in front of this fully clothed older woman. It felt very erotic. I jumped up on the bed, and laid on my back beside her.
“I love your muscles!” Cathy said, as she gently began to run her hand over my chest and down to my stomach. To be honest, my muscles weren’t brilliantly defined, but they were visible, so I was flattered she thought I was sexy. Her hand continued to explore, and after a few minutes of rubbing my chest, stomach and legs, I felt her hand start to slowly creep up my inner thigh. I closed my eyes in anticipation, and within seconds I felt Cathy’s fingers tease the tip of my dick. I was already hard, but feeling her lightly touch my penis made me even harder.
“Oooh, you have no bother getting a big erection, do you?” said Cathy. “Can he stay hard, though, that’s the question!”
I groaned as she took my penis in her hand, and started to stroke it. Her hand felt amazing. Momentarily, she let go, and I opened my eyes to see her spit on her hand then work her spit onto my throbbing cock. Incredible!
Now all this time, Cathy was still fully clothed – she was wearing plaid shorts and a shirt (clearly pajamas). As she stroked me, I reached gingerly over to her shirt, and slowly started to unbutton it. I heard her inhale sharply as she noticed what I was doing. I unbuttoned her shirt entirely, then gently reached inside. My hand made contact with her right breast, very large and firm, with a large, erect nipple. Cathy’s breathing got faster, and her hold of my cock got tighter, the stroking faster.
“Mmm, hmmm!” she moaned. “That’s amazing!”
We continued like this for several minutes, her stroking my cock as I massaged her large breasts. She then stopped, stood up, slipped off her top, and pushed her shorts to the ground, before clambering back on the bed, fully naked.
She was a bigger girl, that was for sure, but she was fully shaven and very well-groomed over all. As she leaned in towards me, our lips met, and I tasted both wine and cigarette on her lips and tongue. The kiss was gentle, sensual, and I could feel her desire. I turned into her, so we were lying on our sides facing one another, and I felt a little overwhelmed by her flesh. I’d never been with such a big girl before.
Our kissing became more fervent, more lustful, and I felt her hands on my back and ass, pulling me in. My erect dick poked into her stomach, so I readjusted my position until it was pointing straight at her pussy. It made contact, and she shivered. As we continued kissing, she took my dick in one hand and began to rub the head over her clit. I could feel folds of flesh, and I could feel that she was wet. She rubbed my dick against her for several minutes, getting wetter and wetter, and faster and faster, until she suddenly braced and orgasmed heavily, shaking and moaning loudly.
“Do you have a condom?” she asked.
I did, so I jumped off the bed and went to get it. I hate condoms. They desensitize and I find it difficult to cum while wearing them, so I was disappointed. She couldn’t get pregnant at 55, could she?! But I obliged and put one one, before getting on the bed and rising on top of her, my hard cock pointing down at her wet pussy.
Cathy grabbed my waist, and then reached down to guide my cock inside her. It felt warm, but not great due to the condom, but I stayed hard and began to fuck her missionary style, feeling myself going in and out. I was actually really enjoying it. It was so different with a fat girl, but I found the flesh and shape of her to be erotic and intoxicating, and the sound of my dick sloshing in and out of her wet pussy was fantastic!
“Fuck me from behind,” she said.
I pulled out of her, she got on her knees and stuck her ass towards me. The condom was taking effect, and I was struggling a bit to stay hard.
“Take the damned thing off!” she hissed at me. “Just fucking do it!”
I didn’t need any more encouragement than that. Off came the rubber, the cock sprung to attention with very little effort, and I lined it up to her pussy. Entering her from behind without a condom felt incredible. She was warm, very wet and I could penetrate very deeply. I could feel her pussy tightening around my dick as we fucked, and I kept thrusting hard and fast and deep, hearing her moan and scream my (fake) name as she climaxed several times.
After several minutes of fucking, she said, “I want you to cum inside me!” Hearing that from a stranger, knowing that I couldn’t do that with everyone I fucked, really turned me on. My humping turned up a notch and it felt as if my cock got harder. I penetrated her with each thrust as deep as I could, thinking the whole time how cool it was going to be to cum inside a strange woman with no chance of any repercussions. I think this thought pushed me over the edge, because moments later I felt my orgasm welling up inside me, the muscles pushing it ever forward, until I absolutely erupted inside her pussy. Deep inside her, my dick was depositing stream after stream of hot cum. It was made hotter by the fact that at that very minute I thought about my Puerto Rican girlfriend, who thought I was at home in bed, when in reality I as cumming inside someone who I didn’t even know.
The orgasm seemed to linger, with more streams of cum than I remember producing up until that point in my life. Cathy screamed in pleasure as she felt it inside her, which was a huge turn on. Spent, I collapsed on top of her for a few moments, enjoying the feeling of my tender cock still enveloped in her pussy, before slowly pulling out, some cum trickling out of her and onto her bed.
“That was incredible,” said Cathy, still breathless.
“It was,” I agreed. I was out of breath too, but was quickly recovering.
We made small talk for maybe 15 minutes, then I got up, dressed, and left. As I drove home, I could feel my dick still wet from her pussy, and I could still taste and smell the wine and cigarettes.
Not long after I was home and collapsed into bed, my phone buzzed. It was a text from Cathy, saying, “Steve, thanks for tonight. I really needed that. You’re the youngest guy I’ve ever been with in terms of age difference, but it was so worth it. If you ever want to do it again, just let me know.”
I went back over there twice after that. On both of those occasions, Cathy tied me up and deprived me of an orgasm until she was ready for me to fuck her. I enjoyed being dominated. My girlfriend never found out. I actually fucked her one evening and then two hours later I was at Cathy’s fucking her. I came inside both of them.
After the third fuck session, I never heard back from Cathy. I saw an obituary for a Cathy Birt in Rossville, age 56, not long after our third session. I don’t know if it was her or not. The sex was incredible, and I’ll always remember her letting me cum inside her.