Delivery Boys – Chapter 8

Chris called Saturday morning to arrange meeting at his place for that evening. I really wanted to see him but could not miss my Saturday evening shift in Delivery Boys Gay Escorts. I told him that I will be working in restaurant that evening. He was not too happy about it but was not pushy either. He is slowly getting his place sorted after moving there. We agree to meet at his place on Sunday late afternoon.

Saturdays are always busy in Delivery Boys Gay Escorts. That is why we stay later these nights. Basically, many guys try to pick up in clubs and saunas but if they are not successful then they turn to several gay escort agencies operating in Sydney. The biggest rush is either in the afternoon and then it gets quiet between 6pm and 11pm. There are always at least four escorts available on Saturday’s afternoon and night. Manager asked me to start at 3pm this Saturday. When I will finish will depend on how busy we get later that evening unless I score two clients – in that case I can leave early if I wish. I guess it is fair proposition.

I spent most of Saturday morning studying. Had a light lunch and douched after that. Checked on my undies in the wardrobe and thought about getting some new ones, more sexy ones. Train ride was pleasant, and I arrived at the escort agency just before 3pm. Manager was happy to see me there as one of the boys did not turn up – called sick, and one will be late. I went to the lounge and then to the laundry as nobody pulled freshly washed towels out of the washing machine.

Just finished putting towels into dryer when manager came to call me out. Client just arrived. Only two of escorts were on duty at that time. The other guy was already in the reception room with the client and I walked in after him.

OMG! He is so…

OMG was first thing on my mind when I walked in the reception room and saw the client. He was short and extremely overweight guy.

“Hello sweetie how are you? Oh, you look so feminine boy. I like that” he asked immediately and then sort of complimented me. 

I went through usual introduction while he was rubbing the bottom of his stomach.

“Thank you and see you soon” he said after I finished.

I walked out of the reception room wishing he does not pick me. This is the very first time I had that feeling since I started working as a gay escort. I heard stories from more experienced gay escorts about this stuff but never thought it will happen to me. That is one negative thing about being escort for an agency. You are not allowed to decline serving the client. To my horror, manager walked in the lounge soon after and told me to go and meet the client.

Well, such is life I guess. I picked towels, condoms and lubricant and went to meet the client. He requested room on the same level. I guess it is because it would be hard for him to walk upstairs. Took client to the room, gave him towels and walked out to get more towels, condoms, lubricant and some massaging oil. And I was not in rush to get back to the room, but it was unavoidable. I would rather provide massage than sex to this customer. 

Customer was laying on his back when I walked in. His penis was already erected surrounded by huge stomach. Balls were hanging – he had very big balls. I undressed slowly and walked towards the bed, placed accessories on the bedside table. 

“Would you like to start with a massage Sir?” Hoping he will say yes to it. That would buy me some time.

He did say yes and turned around with difficulty and puffing. His body was taking good part of the queen size bed. Very hairy back and arse. I splashed massaging oil over his shoulders and started massaging him from side while still standing. 

“Pop on top of me” – he said and I had no choice but to do it.

I massaged his neck that was part of his back. He was puffing all the way. Then I moved slowly down his back and eventually got to his arse. They were like two round topped mountains. I could not see his hole and did not really want to see it anyway. Then he grabbed my arm and pulled me on side, and touched my cock.

Bed gymnastics

“You are not hard” – “I am bottom Sir…” – “You have problem with erections?” – “Sometimes…” – “So young and having erectile problems. That is not good. You should see your doc” – “I am thinking about it Sir” – “You have nice body” – “Thank you Sir”. He turned me on side and was behind me. He was trying to penetrate me but his stomach kept pushing me away. I could barely feel his cock touching my hole but not really penetrating.

After some bed gymnastics on the bed I ended up on top of him. Unwillingly I took his cock in my hand and guided it to my arse after placing condom on it and lubricating. I had to lean backwards and rest on my arms to be able to allow penetration. Eventually he penetrated me and I started stroking while he was puffing. He was stroking my cock at the same time.

Finally, he moaned, his body started twitching. He cum and I was feeling relieved that the whole thing is getting close to its end.  Quickly after getting it off his penis, I took condom of his cock and wrapped it in the tissue. Client was laying on the bed for a while breathing deep and then slowly got up. “It was good. Did you like it?” – “Yes Sir, I liked it…”

“I will shower at home” – he said and started getting dressed. It was only just over half an hour since we got to the room. I took him out after he dressed and walked to the lounge. Now, that was easy money I thought. Escort that was late finally arrived.

The next client arrived some half an hour after I finished with the first one and I asked manager not to go and greet him and it was fine. Not that I was tired from the first one, but I just was not in mood. Around 6pm I was picked up again by a client. It was straight forward vanilla stuff. Nothing to talk about or remember. I could leave after I finished with him but manager asked if I can stay and I agreed to it under condition to leave by 11pm.

Around 9:30pm we were called to present ourselves to the client that just arrived. I was to go in second. I walked in and for the second time this evening OMG was the first thing going through my mind when I saw the client. This time for opposite reason. He was young. Probably not older than me. Dark face, probably Arab gay boy. I stumbled when giving my usual presentation.

“Do you wear female underwear?” – was his first question – “No” (I did not feel using Sir would be appropriate in this case). – “You would look great in female underwear” he said. “Thank you… I am gay… I am feminine…” – “I like that. Do you kiss?” – “Yes, I kiss” and that was all. I walked out somehow confident I will get to see him. And I was right. However, I was not sure if he is gay… When you work as a gay escort you develop some sort of ability to judge people’s real preferences. 

Feminine boys walk “girly” better than real girls

“I had a shower already” client said after I took him to the room. “That is fine. I am going to get more towels, condoms and lubricate and stuff and will be back soon”. I quickly picked what I needed and went back to the room. Client was sitting on the side of the bed in T-shirt and shorts. I took my jeans off and he stopped me from taking my undies off.

“Stay in your underwear and T-shirt” he said. He took the towel and wrapped it around my waist. “That is better” he said “Look like a skirt. Go to the bathroom and walk out like that. But like a girl… You know what I mean? You are so feminine boy” – “I think I know” I replied and went to the bathroom and then walked out like, well, like a girl. Actually, I think that feminine boys like me can do girly walk better than real girls.

“You will resist me a bit” he said and walked towards me and pinned me to the wall. “You are early from school girl” – he said. I got the idea what he wanted to do – “You are squeezing my hand. It hurts” – I said. He squeezed it more and pushed me with his body towards the wall. I could feel his hard cock pressing my stomach.

“You promised to see me last night but did not turn up” – “I had to study” – “Not all the time” – “My father would kill me if he knows” – “You are early from school today. He will not know” – he put his arm behind my back and pulled me firm towards him – “You know I am not allowed…” – “You have another boyfriend? – “No. I don’t” – “What is the problem then? You don’t like me?” – “No. I like you” – he started kissing me and I put my arms around him.

His hand went under my towel and he started pulling my undies down slowly – “You know we are not allowed. I am virgin” – “If you like me then you will give me your virginity” – “We are not married” – “I will marry you” – “I am still in school till the end of this year” – “It is only two more months” – “My parents would throw me out of the house” – “I will take you in my house” – “Not before marrying me” – “I will marry you” – “You have to talk to my parents first” – “Let’s walk in the bush and talk about it” he said, took me in his arms and walked to the other side of the room and placed me down on the floor – “It is quiet here. Nobody can see us” he said while his hands were under my towel.

“I am scared” – “You know me. No need to be scared. I will show you my cock. Have you seen hard cock before? – “No. You know I am virgin” – he pulled his shorts down and his cut very dark cock popped out. I got completely into my role of a virgin girl and like turned my head away not to see his cock. He leaned over and took my head in his hands and made me look at his cock that was only centimetres away from my face. “Oh, it is so big. I am scared” – “Lick it” he said and pulled my face till it touched his cock. I started licking it and then took it in my mouth. He pulled it out of my mouth after just few strokes. I was sensing that he might be close to cumming as his cock was pulsating. “I will be gentle with you”


“Please, let me go. I am scared” – “Just touch it” – I obeyed and started stroking his cock. It was thick and somehow rugged as his veins were pulsating. He took it out of my hands and suddenly pulled my undies off, stretched my legs and got on top of me. I was very hard and I could feel my precum dripping. He made sure that towel was still around my waist and covering my cock.

“Please let me go” – “Nobody can see us” – “It will hurt” – “Yes it will. Girls have to hurt” – “I cannot marry if I am not virgin” – “Nobody will know except me and I want to marry you anyway” – “What if my parents say no to it?” – “I will tell them that you are not virgin then and they will have to” – “They will kill me” – “No they will not. Particularly if you get pregnant” he said as his cock was rubbing my hole.

The client had a lot of precum and my hole was completely wet and I could smell it too. “Please don’t I am scared” – he touched my penis – “You don’t have period? You know, girl thing” – “No, I had it last week” He took my top off – “I like your small tits” – I covered my chest with my hands like hiding from him. He took his top off. Nice, well built moderately hairy chest appeared. He started kissing me passionately, grabbed my legs and placed them on his shoulders – “You will be fine. Little pain and then you will like it” – “I am scared” – he pushed his cock firmly trying to penetrate me but it was very painful and he did not get far.

I am not sure if he had much if any experience in bed – “I need some lubricant” – I got up to get lubricant and condom – “We should use condom” – I said in a voice that was different to my girly-talk till now. “I am clean” – he said – “You fuck raw often?” – “Never” – “Why now?” – “I have never before…” – “Never had anal sex before?” – “No” he said after a pause.

I figured that and was happy to proceed hoping that conversation did not spoil our roleplay. I throw condom on the floor and he grabbed me and pulled me down. My legs were back on his shoulders very quickly. I rubbed plenty of lube on my arse while he was kissing me and then went to put some on his cock. He resisted and I realised he is very close to cumming. “Just relax” – I said sounding like a professional gay escort (well I am). I took his cock in my hand close to his balls and squeezed it strongly (apparently that helps with delaying ejaculation) and held it for a while. His breathing changed a bit and I gently put lubricant on his cock without massaging it too much.

Lovely virgin Arab gay boy

Little help from my hand to guide him to my arse and he pushed it in. I moaned as his thick tool pushed deep inside penetrating me. He was gentle to my surprise. I think he was trying to restrict stroking to delay cumming but it happened pretty quickly. We started shooting at almost same time. I was still in our roleplay and was moaning in a girly voice begging him not to fuck me and that stuff. He pulled out. The fact that I cum made him more relaxed – “Was I fast?” – “No. Just right for me” – I said watching his cock covered with cum dangling above.

He looked at his cock and said – “Girl would leave blood on it first time” – “I am not girl, but you made me feel like it” – I thought it was a compliment. Ten minutes later I parted with him on the door and got a lovely kiss “Thank you” he said and disappeared. “I really love feminine boys more”

I got back, had a quick shower and let manager know I am leaving. He thanked me again for staying after second client and I rushed to catch my train. It was very good night, I thought while travelling. Eh these men – this was the second one who wanted to make me baby. His question about wearing female underwear came to my mind. Maybe I should…

To be continued…

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