I woke up late on Sunday morning, replaying the previous day's events in my head and giving myself an erection. I reached for my phone to cast some porn to my bedroom TV, but checked my email first out of habit. John had sent me an email entitled, "To keep you going. Sarah has approved me sending these," with a Google Drive link.

I opened it and cast it onto the big screen from my phone. John had sent me a selection of high-res photographs of Sarah in various lingerie sets; Sarah wearing various strapon dildos, in assorted outfits including a picture of her wearing a large strapon, a pair of red net tights and high-heeled boots that made my cock instantly hard. 

Also included were a couple of John in stockings, suspenders and a bra, plus some selfies wearing sheer black tights this time with his face hidden by the phone. I wondered if he'd taken these for a website. Finally, there were several photos of them fucking, taken by photographing their reflection in the mirrored wardrobes in the spare room. Sarah on top in two of them, one of him fucking Sarah doggy style and the one they’d sent me of Sarah pegging him.

I brought up the picture of Sarah with the red tights and boots and fixated on that. It wasn’t the same strap-on she’d fucked us with the night before, but a rather intimidating green and red tentacle dildo that looked to be about 9” long with a narrow tip that flared out to a thick base. I initially thought it would be painfully uncomfortable, but I couldn’t stop imagining it up my arse! I wanked myself off looking at that and the picture of John in his stockings and suspenders, hard cock waving around in front of him, imagining Sarah fucking my arse and John fucking my mouth until I shot my load on my chest. I lay back afterwards, wondering about this newfound sexuality. John had said he was bi, but I’d never really felt attracted to men, fantasies about getting my arse fucked aside. Maybe it's a time, place and person thing for me! I did wonder if John had any experience with other men and decided I would ask him when I next saw him.

I got up and showered, remembering how good the different toys had felt in my butt, and decided I needed some. When I finished and had dried off, I got on my laptop and Googled for sex toys. I spent about two hours researching anal toys for men before finally settling on a vibrating, thrusting remote control prostate massager and a seven-inch realistic dildo with a suction cup. I sent my order, then logged back into my email to open the pictures John had sent. I realised I hadn’t replied to John’s email thanking him, so I replied describing the fantasy I’d had while wanking off to the two pictures. That got me hard again, so I stripped off and took several selfies of my hard cock in front of the computer screen displaying their photos, then went into my bedroom and took several full frontal selfies in the mirror with one bent over, showing my arsehole. I sent John the best of each view attached to the email and shut my laptop down.

I had to travel on business again that evening, my old employer was not quite ready to let me fully retire, and I didn’t get back until late Wednesday. I’d had a brief reply from John in my email complimenting my pictures and saying the tentacle dildo was an experience, but I’d had nothing since, which I was a little disappointed at. I was hoping for more pictures, to be honest. I did get home to find a parcel waiting for me with my new sex toys, but I was too tired to open it. I left it on my kitchen table for the morning and went to bed.

Thursday morning, I awoke early, excited to open my new toys, but forced myself to have a shower first to make sure my bum was clean. Once I’d showered and dried off, I took the box into the bedroom, connected my phone to the TV, and then opened Google Drive to look at the pictures of Sarah and John again. I opened the box and examined my purchases. The dildo was fairly standard, with a powerful suction cup at the bottom. I had a vague plan to fuck myself with it to get ready for John, even though Sarah had already fucked my arse with something of a similar size; however, I was dying to try the prostate massager. The two I’d had in my arse the previous weekend had felt fantastic, but too much had been going on for me to focus on them. The larger one with the vibration felt best, so the one I’d bought was about the same size but more sophisticated in what it could do. 

I made sure it was charged and played with the remote to make sure I knew what each mode did, then lubed it and my arsehole. I touched the tip of the toy to my arse and pushed it in. I felt a little discomfort as it opened me up, but no pain. I slide it all the way in, feeling it push against my prostate. I settled back, clenching my bum and stroking my stiff cock. I reached for the remote and switched modes to a pulsing vibration, then played with myself while watching a slide show of the pictures John had sent. I felt that warm, wet feeling again in my arse as my prostate was stimulated and I pushed the button that started the dildo thrusting. My cock twitched as the toy pulsed and thrust inside me, precum leaking from my slit. I stroked my cock, watching the pictures of John and Sarah as the massager did its job. I shot a load of cum onto my chest and hand as the picture of Sarah in the red tights and tentacle dildo was displayed on the TV.

I pulled the dildo from my arse, switched it off and cleaned myself up, then went shopping. I got home, had some lunch, then messaged John to check if we were still on for our lads' Friday night drink. I received a reply almost immediately saying he was looking forward to it, and could we hang around in my flat as he wanted to chat. I asked if Sarah was going to come over with him, but he told me his daughter was home for the weekend, so Sarah was taking her out for a girls' cocktail night.

John arrived at 5 pm on Friday, which was quite early for him, and we decided it was too early to order food, so we decided to have a couple of beers.

“So what did you want to talk about?” I asked.

“Sex mostly!” John laughed, “Sarah said I should fill you in on our sexual history and find out about yours.”

"OK, any particular reason?" I asked nervously.

"Titillation." John laughed, “First off, do you have any questions for me and Sarah?"

I relaxed and took a drink. This should be fun, I’ve always liked talking about sex with partners, which I suppose John now was.

"Am I the first guy you’ve been with? You said you were bi," I asked after a moment’s thought.

"Technically, yes, with Sarah," John replied, "but I had sex with two guys and three girls before I got together with Sarah"

"Technically?" I laughed.

"We’ve had several threesomes with one of Sarah's old boyfriends. She transitioned to female in her early twenties. We first had sex with her two years ago, so she’s been a woman for longer than she was a man!"

"Was it spontaneous or arranged?" I asked, fascinated.

"She came to see us after a breakup, we got drunk, Sarah got flirty, as she does, and we ended up in bed together. Sarah sat on her face while I fucked her arse and fingered Sarah’s pussy and bum."

"Nice!" I laughed.

"After that first time, we met up twice more to have a threesome. She’s very much a bottom and doesn’t get erect despite still having a cock, so it was always me fucking her, which was nice, but I do like to switch."

"Switch?" I asked naively.

"I can be a top or a bottom," John replied.

"Ah, OK. I suspect I am, too. I’ve fantasised about having my arse fucked for years, so Sarah fulfilled that for me, but I would like to explore some more!" I smiled.

"Good to know!" John laughed. "Gina got me properly into cross-dressing. I’d always enjoyed wearing tights and stockings during sex, but hadn’t gone any further. The second time we met up with Gina for a threesome was at her house, and she was wearing some stunning lingerie. She’s about my size, so Sarah asked if she would dress me up. We stopped short at makeup, but I had the full stockings, suspenders, bra, skirt, blouse and high heels."

"Blimey!" I exclaimed, "It sounds like you were having fun. I loved you wearing tights, by the way, one of my top fetishes. Why did it stop?"

"She got back with her old boyfriend," John explained. "I'm glad you liked the nylon, I have the same fetish. I'd love to see your cock in tights.'

"Ah, that sucks that it ended. Maybe I can wear tights for you next time we have a threesome?" I said.

"I would like that very much. Sex with Gina was fun while it lasted, and afterwards we were both keen to try another threesome, but we've not found anyone suitable until you". 

"I’m honoured." I smiled, raising my glass.

"OK, your turn. I know you’ve had at least one threesome. You blurted it out when we were drunk once." 

"Yes, in my mid-twenties. I was in Amsterdam for a conference and hired two prostitutes for an hour. It was fun but brief, and both had fake boobs, which I don’t like. They had a 69 while I watched, then one rode my cock while the other rode my face, and they swapped halfway." I confessed, "I’m not sure it was worth the money I paid, but it had to be done!"

"I can understand that!" John laughed. "Sarah and I were going to have a threesome with a prostitute in Thailand once, but we both chickened out. We decided it needs to be someone we know and like if we're going to share. We did pay two girls to fuck each other while we watched, which we both really enjoyed. "

"No ladyboys?" I laughed.

"We didn’t get a chance, but always said we would if we went back. I mean, get someone over to the hotel to perform for us. Probably."

"Any other group sex experiences? You mentioned having a threesome with Sarah's best friend. I’m going to guess that it was Eleanor?" I asked, naming one of Sarah’s school friends.

I’d met Eleanor a couple of times when we were all sharing a house and got on really well with her. She is tall, raven-haired, dark-skinned and great fun to hang out with. We got on really well but as she’s gay, it never went any further.  

"Yes, you know she’s gay, right?" he asked, and I nodded. "Her and Sarah used to get together when they were in sixth form for sleepovers".

"Oh, I see!"

"She wanted to have sex with Sarah again, and we agreed she could, but only if I could watch. Unexpectedly, she agreed, and it was one of the sexiest things I've ever seen in my life!" John exclaimed, "Three times and each time as good as the first!"

"When was this?" I asked.

"Just before we got married and twice afterwards," John replied. 

"Lucky man, I would have loved to see her naked back then. I wanked a lot thinking about her!" I laughed.

"Yes, she has a fantastic body, but she’s not interested in men at all!" John laughed. "You’ve had some gorgeous girlfriends, though. Sandy, Maisie and Debbie, to name three."

"They were all lovely to look at, but Sandy was toxic, Masie cheated on me constantly, and Debbie wanted kids and left me for another bloke.I have been fucking Debbie recently. She’s the lady I mentioned who likes to use a vibrator on me when she sucks me off."

"Isn’t she still married then?" John asked.

"Yes, with two kids, but her husband’s sex drive is nowhere near hers, so she has affairs. We generally get together a couple of times a month, sometimes for a quickie, sometimes for a full session if her husband has taken the kids out for the day.  She fucked me with the vibrator because I asked if I could do her anally, and she said yes, but only if I went first!"

"I never had that with Sarah, I fucked her arse on our third date on her suggestion." John smiled.

"Nice. The fifth date is my personal best for a girl requesting anal!" I replied, thinking that was actually with John's sister!

"With my sister?" he smiled, making me jump.

"How the fuck do you know that?" I asked nervously. John could be quite protective of his baby sister.

"She told me the night before her wedding. Well, not about the anal, but that you and she had been getting together when you went to gigs. She told Sarah she likes anal when they were drunk once, and that the first time was in a hotel after a gig. I figured it had to be you!" John explained.

"Err, sorry?" I started. I wasn't sorry; it had been fantastic.

"She’s a grown woman; she can make her own mistakes." John laughed. “How come it didn’t last with her?”

“Distance mainly, but me being a dick and not wanting to be tied down. I regretted not making more of an effort once she was married and unavailable.” I sighed.

"OK, I understand. My turn - How many partners have you had?" John replied.

"23, most of which were one-night stands and including the two hookers," I replied honestly, "The men and women you’ve been with. Do I know any of them?"

"One of the guys you know, Davey, and one of the women was Joanne," John replied, naming his best friend at school and the very wonderful Joanne, with whom I’d had casual sex with throughout University. She told me she’d had a night of fun with John when she’d called round for me when I was away for the weekend. That was a couple of weeks before he got together with Sarah, so it hadn't happened again.

"Davey and I were close, and I told him about losing my virginity to another lad on holiday.” John started.

Gpo

‘You can’t just casually lead with that and not give details!’ I laughed.

“We used to go on walking and camping holidays with family friends for a couple of weeks most years. Their son was my age, and we shared a tent together. It started with us talking about a couple of girls we’d seen earlier that day and turned into a masturbation session in the dark. 

Next night, we did the same, only this time we wanked each other off. By the end of the first week, I sucked his cock for the first time, and a couple of days after that, Mike came to the tent with a bottle of baby oil and asked if he could fuck me. I got on all fours, and he lubed me up, using his fingers on me, then pushed his cock up my bum and fucked me.”

“Nice, did it hurt?” 

“Not really, he used a lot of baby oil and he had a fairly small cock.” John chuckled. “It felt great though. We fucked twice a night for the next four nights, always doggy unfortunately. I wanted to experiment, but he wouldn’t!”

“Did you fuck him?” I asked, remembering what he’d said about being a switch.

“We tried on the last night we were there, but he wimped out. That was the last family holiday I went on before University. I think it was just something he did on that holiday for fun. He wasn’t really into guys, but I realised I was. I did fuck a girl called Bev at a Christmas party and a half a dozen more times before I left for Uni. Nothing to tell there really; she was quite vanilla” 

“So how did you end up having sex with Davey?” I prompted.

“He was curious after I told him about Mike and a virgin, so I offered to suck him off." John continued.

"Just once?" I prompted.

"Oh hell no, we used to go to his house after school as his parents both worked.” 

John took a drink of his beer and went on, "Dave was really nervous at first and would only pull his cock out of his fly for me to suck. He was a chubby lad at school and very body conscious. I finally convinced him he might as well get naked since he’d cum in my mouth, and you can’t get much more intimate than that! He agreed, but only with the lights dimmed, and at that point he started to suck my cock too."

"Just oral then?" I asked.

"For the first six months, yes. The lights came up a little as he gained confidence, and we would take it in turns to suck each other off. He had a lovely cock, a little longer than mine but not as thick. One night, we'd been in a '69 but broke away before either of us came because Dave thought he heard a car on the drive. It wasn’t, and as he came back to bed, I grabbed him and we started wrestling. He was bigger than me, so I ended up face down with him pinning me down. I remember vividly how his hard cock felt against my bum and how he started to slide his cock over my bum and quickly shot his load on my back."

John stopped for another drink, his face quite red as he told his story.

"We switched over and I did the same to him, but purposefully slid my cock between his butt cheeks and over his arsehole until I came on his back. We cleaned up as we were running out of time, but the next day we got naked straight away, and he asked me to lie face down. 

He produced a bottle of lotion from underneath the bed and smeared my bum with it, straddled my legs and started to rub his cock between my bum cheeks. He didn’t really seem to know what he was doing, but he was breathing heavily, so I guessed he was enjoying it. I squirmed underneath him, trying to encourage him to fuck me, and finally, his cock hit my arsehole at just the right angle, and his cock slid inside me. He pulled out straight away and apologised, but I told him not to stop and that I’d been wanting this for weeks! He pushed his cock back inside me and fucked me until he came inside me."

"Bloody hell, that’s hot," I said, realising I’d been holding my breath.

"Oh, it gets better!" John laughed. "He rolled off me, lying face down and opened his legs slightly and asked me to use plenty of oil. I oiled him up, slipping a couple of fingers in and out while I oiled my cock with my other hand. I got on top of him like I had the night before, but this time guided my prick to his anus and pushed in. He moaned but whispered, "Keep going", so I slid all the way in. I gave him a minute to get used to having my cock inside him, then fucked him hard, blowing my load inside him in minutes!”

Again, John stopped to finish his beer.

"We fucked and sucked each other all through the second year at the 6th form. There was no real attraction between us; it was just sex. He went on a gap year with some other friends after our A-levels, and I worked for my Dad for the summer. We had sex one more time before we left for University, then I met Sarah and he met Sylvia, so we never did it again." John finished.

I had another drink and shifted in my seat. I’d had an erection for the last 20 minutes, and it was getting uncomfortable. I could see John was in the same boat. He saw me looking and laughed.

"You hard too?" he said.

"Yes, do you want to see?" I grinned, winking at him.

"Yes, and I’d quite like to suck your cock too."

"Is Sarah OK with that?" I asked, excited.

"Yes, she told me to go and have fun with my newfound gay relationship!" John smirked..

I got up and pointed at the bedroom door. John nodded in agreement, stood up and followed me to my bedroom. We stripped naked and got on the bed, lying on our sides facing each other. John reached down and stroked my hard cock, and I did the same to him for a couple of minutes. We looked in each other’s eyes as we wanked each other off. I realised I was enjoying this and the closeness of his naked body. John leaned forward and kissed me on the lips then leaned back and let go of my cock.

"Time to suck." John smiled.

John swivelled round and presented his cock, taking mine in his mouth. I took John's erect penis in my mouth, tasting his salty precum. When we’d done this before, we were both semi-hard, and I was shocked at the size and firmness of John's cock as it slid in and out of my mouth. I reached around and fondled his bum, pulling his cheeks apart to run my finger over his anus. John's mouth felt tremendous on my cock, alternating pressure and working his tongue on my slit. John slipped one finger in my bum, and I shot my load in his mouth, totally unexpected, and a little out of control. Something that hadn’t happened since I was a teenager! His cock slipped out of my mouth as I groaned loudly with pleasure. 

“Bloody hell, you were ready!” John laughed after sucking me dry. “My turn now.”

I expected him to come closer so I could suck him, but he got off the bed and fumbled in the pocket of his discarded trousers, finally coming back to the bed holding a small bottle of lube.

“Oh!” I said.

“Are you up for this?” he asked, a little concerned that he’d assumed too much.

“Yes, please!” I smiled, leaning over and kissing his lips.

John kissed me back, then turned me around.

“Show me your arse,” he demanded.

I got on all fours in front of him and thrust my hips back. John grabbed my buttocks and spread them, his face pushing between them and his tongue sliding over my anus. I groaned with pleasure as he rimmed me and fondled my semi-hard cock. He sat back panting after a couple of minutes.

“NIce?” he asked.

‘Yes, my first time,” I replied.

“Not your last if I have anything to do with it!” he laughed, putting his head down again and licking my arsehole vigorously for another few minutes.

I fell forward on the bed, face down. John opened my legs, straddling one, and I felt his fingers on my bum. He squirted lube onto my arse and his fingers and started to work two fingers in and out of my arsehole.

I moaned again as his fingers left me, and his weight shifted. A moment later I felt his cock push against my bum, so I pushed back to help him in. He’d prepared me well, and his thick cock slid into me with little resistance. I groaned into the pillow as John started to fuck me, slowly at first, keeping his weight on his arms and legs. I started to buck back, encouraging him to go faster and deeper. He leaned forward, resting his entire weight on my back, his legs on top of mine, forcing them to open wider. His cock slid its full length inside me, and he wrapped his arms around mine, kissing the back of my neck as he thrust his cock deep into my arsehole.We fucked like this for five minutes, his cock pressing against my prostate and making me shiver with pleasure, my cock growing hard again under my body.

He slowed, then stopped, slipping his cock out of me and getting off the bed.

“Get on your back and come to the end of the bed.” He instructed,

I slid forward, opened my legs and pulled them back to expose my arsehole to him. John walked forward, his hard cock leading the way, and slid his cock back up my arsehole. 

“Smile for Sarah!” he said, taking pictures with his phone. I smiled and wrapped my legs around his hips as he started to fuck me again, harder this time. I watched him take a couple more pictures of his cock sliding in and out of my arse and shivered again, my fingers finding my nipples and pinching them.

John dropped his phone on the bed, grabbed my legs and fucked me harder than ever. I started to cum and pinched my nipples hard, cum squirting from the end of my cock as he fucked me. I groaned, legs shaking as more cum erupted from my cock as he hit my prostate again. John’s breath was getting faster, and I realised he was moaning with pleasure. He pulled almost all the way out of me then pressed back in hard, holding himself rigid in my bum. I felt him cum inside me, a warm, wet sensation. He pulled halfway out and thrust back in, groaning loudly as he shot a second load inside me.

He pulled out of me with an audible plop sound and I felt cum run out of my bum. John leaned over me and licked my cum off my chest and cock before lying next to me on his back.

“OK?” he asked.

“Yes, that was incredible. I should have done it years ago when I had the opportunity.” I laughed.

“Oh yes?” John asked, turning on his side to look at me.

“A gay friend confessed he had a crush on me once and asked me if I wanted to experiment. I chickened out but always regretted the decision," I explained.

“Well, you won’t hesitate if he offers again, will you?” John laughed, “You’re experienced now!”

“I am, did you send the pictures to Sarah?” I asked, noticing his phone on the bed.

“No, I’ll show them to her later in private. I can’t risk someone else seeing her phone! Shall we order food now? I’m starving!” he laughed.

We ordered a takeaway and had another couple of beers while we waited. We both put our underpants and shirts on but didn’t bother getting fully dressed. The food arrived, and we watched a film while we ate, but I couldn’t get the way it felt when John’s cock penetrated me out of my mind. I took his not getting fully dressed as a good sign he’d want to go again.

I put my hand on his leg and gently stroked him, my fingertips teasing his cock and balls as the film reached a climax. John leaned back and sighed as my fingers explored. As soon as the credits started to roll,  John stood up, pulled off his shirt and underpants to reveal a firm erection.

“Bend over!” he demanded. “I’m going to bugger you again.”

My cock twitched at the word bugger, and I stripped off, knelt on the sofa resting my arms and chest on the back and pushed my bum towards him, my hard cock swaying underneath me.

John lubricated my arse, rougher and faster this time, his fingers moving in and out of me quickly, making me grunt.

“You like that?” he asked, adding a third finger.

‘Yes, very much,” I sighed.

“Sarah has small hands. She can fist me. Especially after she’s been fucking me with that tenticle dildo I sent you a picture of.” John said softly, still finger-fucking me, “She’s already confessed she has a fantasy to fist us both”

My cock twitched, and I looked back at John to see if he was serious. He winked at me, pulled his fingers out of my bum then guided his cock into my arse again. He pushed balls deep in one hard thrust of his hips making my breath explode from my lungs. He grabbed my hips and fucked me hard and fast, giving me waves of pleasure until I could feel myself building to orgasm again. Before that happened, he gave one full-bodied thrust, and I felt him cum grunting with pleasure. He pulled out, then knelt next to me on the sofa.

“Your turn,” he said, offering me his arse.

I got up and lubed my cock, pushing two then three fingers then four fingers in his bum making him cry out. I mounted him, pushing my cock all the way in like he had with me. He grunted and pushed back against me. I grabbed his hips and started thrusting, hard and fast. John looked over his shoulder, watching my face as I fucked him.

“Come on, fuck me hard!” he demanded.

I lost my rhythm momentarily in shock but recovered and pulled my cock almost all the way out of his arse before slamming it back in, my belly slapping his butt cheeks. I did this again and again, getting quicker until I finally shot my load deep in his arse. I held myself inside him and felt his anus contract, squeezing my cock until I slowly slid out of him with a stream of cum.

We cleaned up, and John left for home half an hour later, promising another threesome as soon as he could arrange it. I knew they were just about to leave for a three-week holiday as they’d asked me to keep an eye on the house. I was eager to fuck them both together, but I’d have to make my own amusement until then!