My first time with Bobby

by Shy Stuart

16 Sep 2019 2472 readers Score 9.2 (39 votes) PDF Mobi ePub Txt


As you may have read in the first chapter Bobby is an athlete, a good looking hunk who is never without a girl on his arm, but it's all a façade. Hidden under that macho exterior is a submissive gay man that longs to be on his back with his legs open.

I'm just as much the pussy boy too. Bobby had been helping me with my college course work. Thanks to him I passed all the exams with flying colours. Now with the exams out of the way we had more time to chat with and possibly meet the two older men Bobby had been talking with.

The two men concerned had invited Bobby around sometime ago and although he really wanted to meet them he was a little bit wary. That's where I came in, safety in numbers and all that sort of thing. Not that I would be any help to him in that respect.

I called around to Bobby's flat with the intention of having a bit of fun and chat with the two men to see if they liked me.

I knocked on the door, I could see Bobby peeping through the spy hole he saw me and opened the door. My mouth dropped open when I saw what he was wearing.

It was something akin to a cyclist bib and shorts but it was made of a black mesh material with a red trim. I just loved his smooth broad muscular chest and his plump looking nipples. I knew he had been pumping his nipples the last few weeks and today they looked like flower buds waiting to burst open. I ran my hands over his chest and down his strong arms and pulled him into me for a kiss.

As we kissed he took my hand and placed it onto his ass.

"Wow!", I said, "They're open back".

Bobby turned around and wiggled his peachy ass at me. I laughed and told him he was such a tart.

"I'm fed up of being the macho man, I want to be a pussy boy, a bitch for older men", he said.

Bobby took my hand and lead me into his bedroom.

"I want to show you all my toys"

On the bed were all sorts of toys, I felt like a kid in a toy shop. I recognised the vibrators and the dildo's but there were some other things as well.

"What's that?" I asked

Bobby gave me a horny smile and said it was a double dong, a two headed dildo. We can use it on each other later and put on a show for the two men.

"Fuck!  Like porn stars?", I asked.

"Yes", Bobby replied, "Like two pussy boys eager for cock".

I can't describe how this made me feel, it was lust and excitement, a bit like a thirst, a hunger for gay sex.

I pointed to a  funny shaped black thing and asked him what it was.

Bobby bent over reached between his ass crack and pulled out this funny t-shaped toy.

"It's a prostate massager, like this one", he said.

"It rubs against your prostate and perineum and makes you cum without even touching your cock"

"Bend over I'll lube you up and you can give one a try. "You'll need to loosen yourself up ready for the double dong".

I undid my jeans, looked around at Bobby and slowly peeled my briefs down over my ass cheeks.

He laughed, "You love being the tart as much as me don't you?"

I nodded and told him it came so naturally to me.

I bent over the bed sticking my ass in the air and Bobby lubed and fingered my ass. My head began to swim. It felt so fucking good to act like a submissive.

With one hand he parted my cheeks and inserted the prostate massager up my arse. Straight away I started to dribble cum, I had to take deep breaths to stop myself from cumming. Bobby pulled up my briefs and jeans patted my ass and told me my training had started.

The massager felt like it was going to slip out but Bobby told me to clench on it with my ass muscles.

"Men will love you if you can squeeze their cocks with your ass muscle", he laughed.

I pointed to two yellow rubber cups on the bed and asked what they were. Bobby said it was a snake bite kit, you use it on your nipples to make them bigger.

Bobby said he started with those but now he uses something called supple nips as you can leave them on for hours. He picked up some lipstick that a girl had left on his bedside cabinet and applied it to my nipples.

"This will make the snake bite suction cups stay on".

He stuck the cups onto my nipples. I could feel my nipples being drawn into the cups and they began to tingle.

There were other things on the bed including a leather harness and a rubber dogs tail butt plug.

There wasn't time to play with anymore of the toys as it was time to log into Skype and chat with the two men.

I gingerly sat on the bed still conscious of the prostate massager inside me.

Bobby positioned the laptop so we could be seen on camera. I asked him if he showed his face and he said yes so I agreed to do the same.

We logged in and the two men appeared.

I was shocked at first both men looked older than our respective fathers, easily in their 50's.

Bobby told me that Greg was the guy on the right and Mike the guy on the left.

Straight away I was drawn to Greg. He had grey cropped hair and a black trimmed beard. He looked rugged rather than good looking but I found him attractive. He had a twinkle in his eye and full kissable lips like Bobby. His chest was broad, tanned and hairy with a big tattoo that looked like wings. His nipples were pierced with large rings in them. His biceps were huge they looked as big as my thighs. He had a little bit of a belly but I kind of like that in an older guy. His bottom half was still a mystery but I was eager to see his cock.

Mike was the opposite to Greg. He was clean shaven with short but not cropped grey hair which was parted on the side. He could easily have played James Bond he looked that good. He had an athletic body smooth, with a defined chest and six pack.

Out of the two men it was Greg that excited me the most, he just had a feel of danger about him that appealed to me.

We exchanged all the usual pleasantries about the weather etc then the two men asked Bobby and I to kiss.

I looked at Bobby and we giggled like two school girls.

We both leaned in and kissed each other on the lips.

Simultaneously the two guys shouted "Proper kissing with tongues".

We leaned in again and had a good snog. Bobby is a fantastic kisser he has full lips like soft pillows. Instantly I got hard, I slipped my hard between Bobby's legs as we kissed and he tweaked my nipple.

The two men said they wanted to see our arses and they directed us to kneel on the sofa and stick our bums out.

We both did as we were told. Bobby got a cheer when the men saw the outfit he was wearing.

"Come on Stuart, get those jeans off", they shouted.

I watched myself on the monitor and undid my belt, button and zip and slowly teased my jeans and briefs down over my ass.

Straight away the prostate massager popped out of my ass.

The men laughed and Greg clapped.

Both Bobby and I had very cute bubble shaped arses. Bobby's ass was plumper than mine rounded like a peach. My hole was clearly visible when I bent over whereas Bobby's was hidden between his ass crack.

Mike told me to part Bobby's ass cheeks so he could see his hole.

I stripped off completely then took hold of Bobby's ass cheeks and parted them revealing the black prostate massager up his ass.

Mike told me to remove the prostate massager and rim Bobby's hole.

I did as I was told and slowly circled Bobby's hole with my finger.

"No", Mike said, "rim his hole".

I was so naïve I didn't know exactly what rimming was but Bobby whispered that rimming meant licking someone's ass and sticking your tongue inside it.

To be honest I wasn't sure about doing this but I got down on my knees behind Bobby and gingerly kissed his ass. The two men encouraged me to go further so I parted Bobby's ass cheeks and pressed my face between them. I knew hygiene was important to Bobby so I knew he would be clean down there but even so I was a bit nervous.

With encouragement I buried my head deeper between Bobby's ass cheeks. His ass crack was hot and moist with his ass cheeks like pillows against my face.

I could smell soap but also a very manly smell that excited me and soon I was lapping away and tonguing Bobby's hole. Then men told us to turn side on so they could see my tongue up Bobby's hole and we willingly obliged. Seeing Bobby's pink hole moist with my saliva really turned me on and I really go into rimming his ass.

The men instructed me to spit on Bobby's hole and finger him. I did as I was told, Bobby was gently moaning all the time so I knew he was loving every second. I turned to the men and licked the fingers that had been inside Bobby's hole and the two men cheered and encouraged me to go further.

Next it was my turn to have my ass rimmed. I couldn't quite believe how fucking fantastic it felt having my ass licked. Bobby really feasted on my ass like a man that had been starved for weeks.

Next Bobby showed them the double dong and asked if the two men would like to see us fuck each other.

It was Greg that suggested we come around to their house and have some real cock up our arses instead of a dildo.

I looked at Bobby a bit sheepish and asked him what he thought.

"Hell yeah", he said "lets go".

The two men could see I was a bit apprehensive so they left us to it to discuss it further.

I really wanted to meet the two men but I was a bit scared. I loved the stuff Bobby and I got up to but I was still confused about how I felt. Part of me didn't want to be gay but I knew the feelings would never go away. So with a bit of encouragement from Bobby I agreed to go around and meet the two men.

We grabbed a quick shower together and headed off to Mike and Greg's house.

When we pulled up outside the men's house I was shaking like a leaf, my whole body trembling with excitement.

We walked up the drive and rang the bell. Greg opened the door, he had a pair of jogging bottoms on but was naked from the waist up. Straight away I noticed his hard cock poking out under the material. He shook our hands and kissed us both on the lips. He lead us into the kitchen to meet Mike.

Mike was completely naked, he had a cock ring around his cock and balls which made his balls look huge and his cock purple it was that tight. Mike asked if we would like a cuppa. I looked at Bobby not knowing what to say but Bobby agreed so I did too.

Mike asked Bobby to help him with the drinks and Greg lead me into the lounge. I sat down on an armchair and Greg sat on one of the two sofa's. I really wanted to sit next to Greg but I didn't have the nerve. We chatted about general things then Bobby came in with Mike. Mike sat on the other sofa and Bobby served the tea and biscuits. It was all very civilised until Bobby sat next to Mike and slipped his hand between Mike's legs.

Greg looked over at me and patted the cushion. He asked me if I was shy and I said yes.

"You were brave on cam", he said.

I blushed.

I couldn't resist him any longer and went over and sat next to him.

To be continued...