A new Gentleman Friend

Well it’s been a while since I made a new playmate and decided I wanted a new one, an older guy again like Patrick, my older gentleman friend. So I joined a few sites and checked them out and decided on one of them that seemed to be fairly good and not many time wasters, so I paid for a full membership for a year. I create my profile with all my usual details and mentioned I was looking for a regular older gentlemen to have fun with, in the 50’s to max of 60 age bracket (I like older guys). Single , No beer bellies, which is an absolute turn off for me and a guy who look after themselves the best they can.

It didn’t take long before I got quite a few message, a lot of them the usual time wasters, some of which were literally one liners, they went straight in the bin, one guy stood out the most, he wrote quite a nice response which showed he was serious and here’s what he put.

“Dear Carrie,

I hope this email finds you well.
I recently came across your advertisement looking for older gentlemen playmates, and I am intrigued. Allow me to introduce myself; my name is James Harrington, and I believe I fit the profile you are seeking.
At 53 years old, I have a mature outlook on life, a wealth of experiences, and a keen sense of adventure. I am eager to explore new connections and share enjoyable moments. I value stimulating conversations, genuine companionship, and the excitement of building new
share a bit more about myself, I am currently single and recently divorced. This new chapter in my life has given me the opportunity to rediscover my passions and embrace new experiences. I prioritize looking after my health, maintaining an active lifestyle through regular exercise and a balanced diet. I am particularly interested in exploring the sexual pleasures and intimate connections that I may have missed out on in the past. I am looking forward to meeting someone who appreciates life’s richness and is open to exploring a meaningful and passionate connection.
If you are interested, I would love to know more about you and discuss how we might complement each other's interests and desires.
Looking forward to your response.
Best regards,
James Harrington”

I logged in and saw that he was online , I checked out his profile and saw the few pics he’d put on there, he was quite handsome, he was 6” tall, His hair, a mix of silver and dark brown, neatly styled, complementing his well-groomed beard that adds to his mature and refined look, so I responded to his email and said I’d be interested in having a chat and see where it goes, so we started emailing back and forth for a day, I quite liked all his responses and so I setup a webcam chat with him for that night, which he said he couldn’t wait. So the evening came and I logged in and waited for James to arrive in the chat and he did so exactly at the time we arranged, another sign of not a time waster. We began chatting and he told me about his recent divorce from Claire, who he had met in their twenties, and that they had a good life together, no children as she was not capable of having them which he was fine with. James mentioned he wanted more passion and adventure in the bedroom, but Claire was conservative and reserved when it came to intimacy, preferring to keep things simple and familiar. She was uncomfortable with experimentation, viewing it as unnecessary and perhaps even a little distasteful. He respected her boundaries, but the lack of variety and excitement left him feeling unfulfilled.

He tried for years to get her interested in the bedroom and nothing worked, so he made to decision and divorce her, which was amicable . Now he was free and single and wanted to find out what he had been missing, and hence why he was on this site. We talked for ages and I told him about me and Carl, we swing and some of the things we got up to and he loved the fact that me and Carl just made the most of life and have fun wherever possible, so we connected on that wavelength and he was very easy to talk to. We spent the next week webcamming and I thought we’ll spice things up a little , so on our chat I said to him ‘OK, I want you to whip out that cock of yours's, I would like to see it”.

I didn’t have to say it twice, he shuffled his trousers down and positioned the camera to point at his very erect cock, now he was a good size , about 7” I thought, but he had a huge nutsack, I looked up and down his shaft and it was a very suckable cock and was looking forward to playing with it.

“Ok, your turn now, let me see those nice tits of yours”, he said. I pulled up my pyjama top and showed him my ample cleavage. “Mmmm, nice, they are gorgeous”. We carried on talking about sex and kept our tits and cock on show.

“One thing I’ll mention is I am a VERY heavy cummer, I mean like bucket loads, and I can repeat it as well.” He said. At that point, I got tingles in my pussy, as you know I love cum and a lot of my FWB’s are not big cummers.

“Oh, that sounds fab, good job I love cum then isn’t it” and we both had a giggle.

“So I think I’d like to meet you then, we’ve been chatting long enough , one thing, on the 1st meet , Carl will be there for a short, he’s always there especially on the first one” I said to James.

“I completely understand, and that’s absolutely fine”, James replied.

“He’ll drop me off , we’ll chat and he’ll leave us to it for a few hrs”, I responded. So we setup a meeting for tomorrow afternoon at 1pm, which was a Sunday and James texted me his address, which wasn’t far at all, Sunday came in no time at all, so I showered and put on a nice casual outfit, nothing too fancy, but came off easy enough, shaved in the right areas and we set off. We pulled up outside his house , which was a nice detached property, quite private too, which was nice, and he saw us pull up and greeted us at the door and we said our hello’s and we gave each other a kiss on the cheek and a hug, and he shook Carl’s hand.

He was smartly dressed, jeans, t-shirt and a tracksuit top, he smelt very nice.

“Would you like some tea or coffee” he asked as we sat out his kitchen diner table , we both said coffee and we chatted some more and have a laugh and a giggle. James was very pleasant , he had a nice way about him, and from what he told me about himself, he was well travelled and had a nice glow to him. We chatted for ages and then James popped to the toilet and once he left the room , Carl said he was happy to leave me here with him and he’ll pop over to one of his sluts house as he had messaged her while we were chatting to see if she’s free, which she was, which conveniently was only a 10 minute drive away. James came back in the room and Carl said he was happy to leave me here with James and he’ll back back around 4.30pm, which gave us plenty of time to have fun. I kissed Carl and James showed him out.

James came back into the kitchen, I had my back to him and he came up behind me and cupped both my tits in his hands and said “Alone at last” and began to kiss my neck, which was lovely, I reached back and stroked his head and one hand on his legs and I moaned softly. I turned around we had a full on kissing session, lot of tongue, our hands all over each other. After about 5 minutes I said “Let’s go upstairs into the bedroom”, he nodded and he followed me up, touching my ass along the way. He pointed me to his bedroom, which had a king-size bed in it, plenty of room to spread out and have fun. We began to kiss again and I undressed him, pulled off his top and t-shirt, undid his belt, pulled his zipper down and his jeans dropped to the floor and he kicked them away, he just had his brief on with a huge bulge in them. I stroked the bulge and he moaned softly, I pulled down his briefs and they also dropped to the floor and he kicked them away next to his jean, he was full starkers now. Now his ball sack was indeed very big and he was standing to attention, I cupped his nuts in my hands and gave it a gentle squeeze.

I backed away from him and began to undress, I pulled off my top, my bra and my trousers, all I had left on was my crotch less panties and suspenders.

“Wow, you are gorgeous”, James said, I smiled and could see the tip of his cock was glistening in the light with pre-cum, I walked over to him, we kissed again and I dropped to my knees and began to lick the tip of his cock, tasting the sweet taste of pre-cum, I then began to suck on his meat as much as I could take in, James groaned loudly, he was certainly enjoying himself. He put his hand on my head and began to gently fuck my mouth. I grabbed his balls and squeezed them, along with lots of slurping noises. He reached down and played with my tits and squeezing my nipples, which I groaned at sucking his lovely cock and being touched.

I stood up and told him to lie on the bed, to which he did and we 69’d, James now had to my pussy which was now inches from his face, he put his hands on my ass and began to lick my wet pussy and groaned with each lick, he was enjoying it, I carried on sucking his lovely cock, running my tongue down to his balls and back up again, he groaned loudly each time. He was now deep probing my pussy with his tongue, lapping at my juices. I got off him and went over to my bag and pulled out some condoms and lube, I opened one and began to put on on his cock and he smiled as it covered his cock. I lay next to him and he immediately got on top and I guided his cock into my wet hole, we both gasped as he impaled me. I wrapped my legs around and he began to fuck he deep and slow, kissing me all over, sucking my tits and groaning heavenly.

He certainly filled me up and it didn’t take long for me to cum, I groaned loudly as I came, James pounded while I came, which was great as it made my orgasm more intense. Once I had stopped he resumed to the slow deep fucking he was giving me, he pulled out and asked me to get on all fours, I did as instructed and he pushed into me again, grabbed both hips and slow fucked me again, his ball sack slapping my pussy, it’s what gave me my orgasm in the first place, he grabbed both my tits and began to speed up the fucking, pinching my nipples, both of us groaning, he began to call me a whore, slut, cock slut and anything else he could think of, he knew I loved be called slutty names when fucking.

We lay down and began to spoon, his cock was certainly filling me up , While James wasn’t looking I put some lube on my fingers and lubed up my ass, I wanted him up there. We spooned for ages, turning my head to kiss and he played with my tits, I pushed him out and guided him to my pucker, as he slid in, he said “God yea, Fuck, that’s tight, Christ”. He slowly slid in all the way to his balls and began to fuck me . I turned round and kissed him and talked dirty to him and said.

“You like my ass don’t you?, come on fuck me hard, give it to me, I want to feel you explode in there”

Well he began to fuck me faster now, groaning loudly with each thrust and within a few minutes , he tensed and I felt the explosion into the condom, he pushed deeply into my ass with each squirt, “Yea, that’s it, fill me up, come on give it me” I said to him, his body twitched with each squirt, It was indeed a big load from what I could tell and he eventually stopped, out of breath and panting, we lay there for a little while and then we kissed.

“Fuck, that was amazing, I’ve never fucked someone in the ass like that”, he said with a huge grin on his face, he pulled and I turned around and saw the huge load in the condom, I was not disappointed.

“Mm mm, now that’s what I call a nice load, very full” I said and he smiled, I pulled of the condom and sucked his still erect cock, tasting his cum, which was delicious, he groaned and his cock twitched with each flick of my tongue. Once I had the last drops out of his cock, he got up and I handed him the condom and he went off to the bathroom and freshened up, my ass was gaping from the fucking it had just had. I lay on the bed and James came back in and gave me a huge kiss.

“That was amazing, now this is what I was looking for, these are the things I’ve missed out on”, he said with a huge grin on his face.

“Good, I enjoyed it too”, we lay there just chit chatting, touching, I wanked his cock and he played with my pussy and tits, some fingers got inserted as well while played and chatted. It wasn’t long before he was ready for round two and James was very horny, I grabbed a condom and put it on his cock and he immediately got on top of me and began to fuck me hard and fast.

“Oh, someone is horny” I said in between groans, James just smiled and proceeded to pound my pussy. He did this for a good 15 minutes and he began to tense and again filled the condom to full capacity, his body jerking with each squirt and he pushed his cock deep into me. He lay there for a while on top of me panting and puled out and yep sure enough the condom was brimming with cum.

“Mm mm, another big load for me”, I said to him and I pulled off the condom and sucked his cock again, I knew he liked it. Once I had performed the clean up duties, he again went to the bathroom to clean up and when he came back he immediately got between my legs and licked my freshly fucked pussy, he sucked on my clit and he knew exactly what he was doing, he shoved two fingers up my ass and fucked my pucker, it didn’t take long for me to orgasm, I grinded my pussy all over his face as I came, smearing my wet juices all over his lips and chin. Once I had stopped he got on top of me and we kissed, I could taste my juices on his lips and tongue.

“Only fair you get to cum too”, he said with a smile on his face, we kissed again and I said “ooohh yes, I did”. We again lay on the bed, just chatting and James asked if I’d like to watch some porn while we lay here and I said yes of course, a gangbang movie, some whore getting all her holes filled with cock and cum by about 6 guys.

“You’ve done that haven’t you”, he asked, “Yes, quite regularly , it’s amazing, having loads of cock to play with”, I replied.

He smiled, “so what’s the most you’ve had in one go then” he asked.

“Well, I’ve had 15 guys in one session, let me tell you, it was amazing, I had so much cock and cum in every hole, I’ve done that a couple of times” I said with a cheeky grin on my face. James’s face was a picture, he was amazed at how many I’d fucked, but also very happy as he knew this was going to get better and he was glad to have met me. This was the start of a good thing. We watched the porn movie and we cuddled, his hand on my tit and my hand on his cock. I noticed on the bedside table was a small glass, empty and big enough to hold his load, so I had a dirty thought. I was going to give him something he had never had before, I was going to drink his cum out of a glass in front of him to show my utter slutness. It wasn’t long before he was nice and hard again and I got him to stand by the bed next to the bedside table.

I dropped to my knees and began to suck his cock, I gave him a slow, deep sucking, he groaned at every stroke of my mouth, I made loads of slurping noises and groaned as I sucked his manhood, after a short while he grabbed my head with both hands and started to fuck my mouth, I knew he wasn’t far off, I looked up at him and he had his eyes closed, so I grabbed the glass of the bedside table and he began to tense so I stopped sucked and wanked his cock off and held the glass at his tip and watched as he unloaded the lovely white creamy nectar into the glass, he was now watching what I was doing, his face tensing with each squirt. He gave about 5 huge jets of cum into the glass, which was now very full.

I sucked his cock once he stopped and he watched me intensely as I pleasured him. I got comfy on the floor and poured the contents of the glass into my open mouth, I looked at him whilst doing this, he was grinning from ear to ear, I showed him the contents of my mouth and swallowed every drop, licked my lips and began to lick the last drops from inside the glass.

“Did you like that little show I put on for you”, I said with a slutty grin on face.

“Hell yes, never seen anyone do that before”, He replied.

I wiped my finger round the inside of the glass and managed to get a bit more cum. It was getting near the time for Carl to pick me up as we had been playing for quite a while, so we both got dressed and it wasn’t long before Carl turned up, he pulled into the driveway and I thanked James for a great afternoon and we hugged and kissed and said I’ll be in touch and went home. On the way home, Carl asked how it went, to which I told him he came bucket loads and fucked every hole and I swallowed him on the last one, he smiled and I asked him how his whore was, he said she was very horny, she had invited one of our friends over as well, Simon, and they filled every hole possible.

Shortly after getting home, James sent me a text, thanking me for a wonderful afternoon and showing him what he had been missing all these years and couldn't wait for another session. I met James again later in the week and had another condom full session, I always use condoms on the first two meets, I like to break them in. James did not disappoint on that meeting I can tell you. The third meeting was going to be the bareback session, which was only in a few days as he wanted to see me weekly at this point which I didn’t mind depending on what else I had going on.