Let me preface this by saying this story is 95% true. I say 95 because it happened around 10 years ago and the fog of time makes fools of us all. I’m also not a writer by any means of the word, in fact this is my first decent attempt at writing anything since high school. This story won’t include any unrealistic expectations regarding sex or sexual experience, primarily just my feelings and opinions at the time. If this goes well I have a few more true stories like this one I could share. All of these stories took place in Sydney, Australia. Names have been changed to protect identities.

Story Description: Inexperienced young man meets mature couple via internet who organise a meetup and indulge in a threesome.

From a reasonably young age, probably around 11 or 12, I discovered internet pornography. This initially stemmed from spending too much time on websites like newgrounds or ebaumsworld and slowly overtime getting exposed to more and more mature content. By the time I turned 18 I personally felt pretty experienced sexually, well without actually having done anything physical. I assumed after turning 18 that it would be easy to find a partner, but unfortunately I didn’t have the self confidence to actually talk to anybody. I occasionally paid for private shows on cam to cam websites, but that was as close as I really got. This eventually led me to adult matchmaker websites which is where all of these stories originally stem.

I had paid for a membership on one site in particular so that I could see photos, send messages, and actually get noticed. Unfortunately for me there weren’t a huge amount of people who were interested in a single 19 year old male. Don’t get me wrong, I don’t think I looked half bad (6 Foot tall, slim, pasty white, brunette, with some well-defined biceps), but the age seemed to be a killer to most conversations. I consider myself to be straight with some bisexual tendencies. I’m not attracted to men at all, but don’t have any issues being around them in a group setting. I’m also pretty fond of Transgendered Women. Basically so long as they looked like women I didn’t really mind what was downstairs, and had no issues playing with it.

One of the responses I got on this website was from a couple in their late 50’s. From the pictures on their account she seemed a bit short, maybe around 5’3”, short black hair with bangs, a little chubby, perfectly shaved, and some pretty sizeable E cup natural breasts. I don’t recall if there were any photos of him. We started messaging back and forth, then shared phone numbers. I then received a phone call, originally expecting it to be him on the other side, but it was her. Her name was Mary, and she said his was Richard. She asked me a lot of questions about what I was looking for and why I was on the site. I explained a bit of my backstory and that to me age is only a number, and that I feel attracted to women of any age, but more so for women with a bit more maturity and experience. She suggested I should meet them both for coffee.

They lived about an hour from me by train and at the time I didn’t own a car, but I wanted to make this work. I caught the train to a shopping complex near them and we met and had coffee. The conversation was much more innocent then I’d anticipated, but I suppose we were out in public. We really all just wanted to get to know one another. I spoke about my current studies, crappy job, and dreams for the future, and they spoke about their life together, kids that have moved out of home, grandkids, and what they get up to in retirement. At the end they decided that they wanted to invite me over for a fun night soon if that’s what I wanted. I agreed and we organised it for a week or two later on a Friday night. They had also mentioned that they’d prefer If I was shaved or neatly trimmed downstairs. I had never shaved before and had quite a thick bush, so this led to me shaving for the first time in preparation.

It was now Friday evening and I was on the train headed towards their house, and I was feeling a little bit nervous about what to expect. It’s worth mentioning that I had had two sexual experiences by this point through the website (possible future stories) but neither of which had involved vaginal penetration so still technically considered myself a virgin. I never told them that though.

When I was a few minutes out from the station I gave them a call and they told me they were already waiting and that they would pick me up from the carpark. When I saw Mary I thought she looked stunning. She had bright red lipstick, was wearing a full length black coat, knee high boots, and a tight white knitted sweater perfectly showing off her breasts. We got in the car and they drove the 5 or so minutes back to their house. When the car was parked in the garage and got out Mary pulled me in tight and gave me a deep passionate kiss. This initially caught me off guard as I’d never been kissed quite like this before, but I leaned into it and it was amazing. When we stopped she said “Welcome to our house, make yourself comfortable” and smiled.

When we got inside we sat down around their dining room table. Richard asked what we wanted to drink. Mary said she wanted a glass of white, and I asked if they had any bourbon. To my surprise he had some Jack and Coke premixed cans in the fridge, so we had a drink and were just talking about life. Richard was telling me about when he walked the Kokoda Trail some years ago, Mary was telling me about the cruises that they enjoy now since retirement. I asked about their home as I considered this to be a bad part of the city, but their house was so nice and modern. Richard explained that when they were buying a house they had to make a choice. Buy the worst house in the best suburb and be considered the “Shit of the Kings”, or buy the best house in the worst suburb and be considered the “King of the Shits”, so they chose that. It made me laugh but it’s certainly something that stuck with me from this experience.

I asked if they’d done anything like this before and they said they try to every now and then since all their kids had moved out. They mentioned that they had a pretty regular partner for 5 or so years until he turned 30 and moved away. Mary then excused herself and Richard said we should move to the living room and keep talking. A few minutes later Mary emerged wearing what I can only describe as a skin tight fluro-yellow dress that went down to just below her round ass, and had a few holes in the material to reveal skin underneath. I was honestly in shock, then Richard jumped up and said “Wow, you look amazing honey” and started making out with her passionately whilst feeling her up. I remained sat on the lounge feeling a bit awkward about the whole situation. Richard then stopped kissing and said “Don’t be shy, come on over and kiss my wife”. I did as I was asked, It was even more passionate than before. Richard then grabbed my hand and placed it on Mary’s breast. I squeezed hard and she let out a moan through our kiss. My cock was starting to get very hard inside my jeans. We were probably standing and taking turns kissing and feeling up Mary for about 5 or so minutes, when she took a step back, stripped out of the dress, and said “come on boys, time to go upstairs”. On the way upstairs I noticed a few small Statues with huge penises, possibly from Thailand or South America, and erotic art all over the walls, this gave me more insight into how sexual Mary and Richard really were. I asked Mary what they wanted in terms of protection. She said they they’re both clean and get regular checks, and that she’s way to old to get pregnant again, so it was entirely up to me. I decided not to use any.

When we got to the bedroom she sat down on the edge with her legs spread wide and said where do you want to start. I had always wanted to eat pussy so decided to start there. I got on my knees, spread her legs, and went to town with my tongue. It tasted different to what I expected, I now understood the fish analogy, but it was still turning me on. Richard had joined her on the bed and was making out with her some more, but the moans which slipped through was making my cock harder and harder. I soon heard Richard say “I bet you want to see his cock don’t you”, she said “Yes please”. I stood up and removed my shirt. She stood up, gave me a quick kiss, turned me around, and pushed me back onto the bed. She then undid the button on my jeans, and promptly pulled off my jeans and briefs together, leaving me now just as naked as she was.

She slowly crawled up over my body giving my rock hard 7” cock a glance, then stared into my eyes with a lustful gaze as she licked the length of my shaft while I was throbbing. She then slid the full length of it into her mouth and started sucking up and down. It took all of my mental capacity not to cum then and there. I then felt a deep moan on my cock and I looked up to see Richard had now stripped off and was fucking Mary from behind whilst my cock was deep in her throat, and she was absolutely loving it. After a few minutes Mary hopped up and said “I want you in me”. She turned around and lay on her back on the bed. This was it, I was about to “officially” lose my virginity. I climbed on top a little clumsily and slowly lined up and slid my throbbing cock into her pussy. It felt fucking incredible. I was pounding harder and faster into her, in a way kind of losing control of myself. She was moaning and without being aware I was getting very close to cumming. I tried to stop but I was already too far gone and started pumping shot after shot of cum deep into Mary’s pussy. I felt a little embarrassed and didn’t want her to know that I’d cum so I didn’t moan and tried to keep going. This lasted for a minute or so before everything felt weird so I pulled out and said I needed a drink of water. She pointed me to the bathroom and said not to be too long.

In the bathroom I grabbed a drink and took a few minutes to compose myself. I didn’t want to return whilst soft so I pulled out my phone and put on some porn. After a minute or two this did the trick and I was able to return to their bedroom.

When I returned Richard was eating out Mary. I was a little mortified as I’d just cum in her, but he looked up at me and said it was delicious and gave me a wink. It was clear to me that Richard was into men as well and I wasn’t quite sure how to handle this so I just tried not to think about it. As I crouched down next to them Richard reached for my cock and commented on how nice it was. I nervously told him I appreciated the comment but that I wasn’t into men and I’d prefer if he didn’t touch me like that. He seemed to take it well, then Mary said “don’t worry Rich, I still can” as she grabbed hold of my cock and started stroking it with a tight grip. I then noticed her breasts were jiggling up and down while Richard was still eating her out. I leaned down and put her nipple in my mouth and started sucking while squeezing her breasts with both hands. She let out a huge moan and squeezed my cock even tighter.

After a few minutes Mary said “I need you both”. I was unclear as to what that meant, but Richard immediately shot up and lay on his back on the bed. Mary climbed on top of him straddling his cock and sliding it into her pussy, then leaned forward spreading her cheeks and asked me to stick my cock in her ass. I did try but was having trouble keeping it up enough to enter. She said “Please, I need your cock”, but I just couldn’t. In the end I licked my fingers and used them in her ass instead which seemed to satisfy her enough.

Soon enough she asked me to move around the front and stand over Richard so that she could suck my cock whilst still riding him. She was vigorously sucking and sucking until I couldn’t take it anymore and I came in her throat, and on her chin, which dribbled out over her voluptuous breasts and down onto Richard’s face. She then leaned down and started kissing him swapping my cum back and forth whilst he fucked her harder and harder eventually cumming and letting out a huge moan.

After this we just lay side by side for a bit, eventually deciding to get up and clean up a bit. Mary directed me to a spare room where I could stay for the night. She gave me a goodnight kiss, then left me in the room. I put on my briefs and a singlet and climbed into bed. I could here light music playing and mumbled talking from downstairs. I lay awake on my phone for a bit, and over analysed what just happened, thinking I’d done really bad and that I’d ruined the night for Mary and Richard. Eventually I got tired and fell asleep.

A few hours later whilst still asleep I started feeling something. I initially wasn’t sure what it was but it felt great. As I slowly woke up I realised that Mary had climbed into bed with me, had removed my briefs, and was rubbing my cock. It was still dark but I reached over running my fingers through her short hair, then pulling her in for a kiss. I asked if Richard was here, she said that he wasn’t, and that he was happy sleeping but wanted her to make the most of my young cock whilst it was here. She then climbed on top and slid my hard cock into her pussy. She started bouncing up and down with her huge breasts right in my face, it was incredible. She kept it up for a few minutes until I couldn’t last anymore. I let out a massive moan and ejaculated stream after stream of my thick cum deep into her womb. She then gave me a deep kiss then climbed off. She cleaned the cum off my cock with her tongue, and climbed out of bed. Right before leaving she said “keep your pants off and go back to sleep, I’ll be back soon. I was stunned but super excited. It was really hard to fall back to sleep but soon enough I managed.

About an hour later I slowly awoke to that good feeling again, only this time in was her lips that were tightly sucking on my cock. After she woke me she gave me a kiss again, lay on her back and asked me to climb on top. I slid my cock in her tight pussy and started thrusting. It felt amazing and Mary was moaning the whole time. She asked me to tell her when I was going to cum, as the last times I had given no warning. I took that on board and fucked her hard and fast for several more minutes until I felt it again. “I’m cumming” I said to which she responded “Yes! Fill me up!”, so I gladly obliged. Afterwards she cleaned me up again and said the same as before, “see you in a bit”.

She slipped back into the room a couple more times that night, swapping back and forth between cowgirl and missionary positions, and each time I lasted a bit longer, and learned a little more about what made her feel good.

I woke up mid-late morning the next day to the sun shining through the window. As I left the bedroom I heard Mary and Richard talking in their room. I knocked then walked in and they Mary said “Good Morning Stud”. Richard said “I hope you enjoyed yourself last night, she just keeps going like the energizer bunny”, then laughed. I said “don’t worry, she did an amazing job”. Mary then asked if I wanted to join her in the shower, I couldn’t refuse.

The shower didn’t lead to any more sex, but it certainly was an extremely sensual experience. She covered the shower loofah with soap and lathered up my entire body, giving special attention to my cock. I then got to lather her up, spending a lot of time with her amazing breasts. We then rinsed off and made out passionately for a few minutes before hopping out and drying up.

We got dressed and went downstairs where Richard had made us all some breakfast. After 20 or so minutes we all hopped back in their car and they drove me back to the train station. We all said how much of a good time that we’d had and couldn’t wait until next time to do it again. I gave Mary one more kiss, shook Richard’s hand, then walked over to the platform to wait for my train home.

All in all I felt really awkward following the experience, but over time I came to understand this experience helped me discover my boundaries and comfort zones, expand my sexual horizons, and build my self confidence.

If you got this far, thanks for reading. Like I said this is just one of a handful of similar experiences I had 10 years ago, and If you enjoy this one I’m happy to share the others.