Sandy Liberates Me Ch. 2

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Things get really wild and adventurous with the guys.
1.5k words
4.49
91.5k
9

Part 2 of the 2 part series

Updated 11/02/2022
Created 07/29/2002
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I decided to call in sick the next day. I was exhausted from a night of love making with Sandy. My ass was also a little sore, so I did not fancy sitting down in an office all day. We had also talked for hours. We knew each others every intimate secret before long. Sandy had not had many lovers, and I was her first since she had a couple of operations to become more feminine. She did not want to get rid of her cock though. How she was now was she wanted to be.

After a short sleep we slipped into her bath together, fondling each other all over. Then Sandy came to the conclusion that I needed to free myself of all my body hair. She set about shaving me from my chest down. I had never felt like this before – so smooth and fresh. It was sexy. I could not believe the way my cock looked with all the hair from balls gone. When Sandy sucked on my balls I nearly came right away. But she told me to save it for tonight.

We stayed in most of the day, but as the evening approached and we had finished a bottle of wine, Sandy said it was time to get ready to go out. “But I don’t have anything to wear, I’ll have to go home for a while.” I said.

“Don’t worry, you are going to wear something out of my closet tonight.” Replied Sandy.

I thought she was kidding when she presented me with a shiny blue dress. She had me dressed in sexy underwear and wearing a blonde a wig. I was starting to look like a woman and not a bad looking one at that. What was I doing. It must have been all the alcohol, because I did not put up much of a fight. We headed out, dressed as two women.

Sandy led me into a bar she said she frequented from time to time. She told me it was a place for guys to dress as women and be themselves. But then she gave me a challenge. “You know what would be really sexy, is to watch you go up to a guy who comes in here looking for someone just like us, and to suck his cock right here.”

I looked at Sandy thinking she was joking. “No way and certainly not here in front of everyone.” Sandy’s reply was “why not” and she pointed to 3 other couples clearly sucking each other off in various parts of the bar. “wow” is all I could say. Sandy then pointed to a guy standing at the bar who was clearly looking our way. “Go, and make sure you use a feminine voice – remember your name is Kylie.”

“Hi, I’m Kylie.” I said

“The name is Bruce. So pretty thing, you look beautiful and innocent tonight.”

I blushed as he guided my hands to the outline of his cock. If I thought about what I was doing I would have run. I should have run to be honest. But I wanted to please Sandy. I could see her watching closely as I undid Bruce’s fly and pulled his cock out. It was at least 8 inches long and quite thick and uncut. I knelt down and took him in deep. He held my head down and forced me to engulf it all. I was sucking hard as he thrust into my mouth. A crowd had gathered around to watch as Bruce fucked my face. In no time his cock was pulsing and cum was shooting out down my throat. He held me there making sure I took every last drop.

Sandy led me away telling me how sexy that was. I was greeted with a lot applause and lot of thanks from Bruce.

“There is a room out the back I am going to take you to now. I want you to position yourself on the bed and look as sexy as you can in your dress. Then when I signal you, you must remove all your clothing and lie down on the bed. Then I want you to service everyone who comes into the room in the next hour. After that, we will go home and it will be just the two of us for the weekend.”

I was so mesmerized by Sandy and everything I had already done this weekend that I barely questioned what she was asking me to do. I was hornier than I could ever remember. So I walked into the room and lay on the bed looking as provocative as I could. The room was surrounded by windows with all sorts of people gathered watching me. I was enjoying being watched.

Sandy signaled me to start removing my clothes. Some music came on to help me be as seductive as possible. Then Sandy’s voice came over on aloud speaker – “This is Kylie – who until last night had never experienced being with a man before. He wants to experience anything you have to offer.”

With that I was naked on this bed as at first two men entered the room. The one looked to be around my age, but a slightly bigger build, while the other was at least 10 years older than me and thinner – he looked like he worked out. They were both naked as they entered the room. Their cocks were clearly already getting hard. The younger guy lay down on the bed and pushed me between his legs. He urged me to take his cock in my mouth. As I began to lick it and get it nice and wet, the older guy positioned himself alongside my face also and started to rub his cock against my cheek. I then took turns sucking both guys. But fairly soon the older guy pulled away again. Then I felt his hands on my ass and a finger pressing against my hole. Meanwhile I still had the other guy in my mouth, sucking hard on his 7 inches. I nearly swallowed the cock whole when I felt the older guy pushing his cock against my ass which was perched at the end of the bed – with my knees on the floor. He rammed his cock into me hard. The mouth full of cock stopped me yelling out in any pain. When I moaned it seemed to stir the younger guy’s cock and before long he was filling my mouth with his juices. Seeing him cum set the older guy off and he filled my ass with his juices.

I barely had time to think when next walked in a group of ten guys. They were probably all around my age and looked to be a part of a football team judging by their builds. Each one approached me to suck on their cock for just a few seconds to get them all wet and give me a taste. Then they ordered me to lie flat on my back. With that they all started to jerk their cocks. Within a couple of minutes they had covered my body with their cum. They then each took turns allowing me to suck them dry.

I was surprised to see that it was a woman who walked in next. In fact there were three of them. They were all a few years older than me, and all with a slightly larger build without being fat. They weren’t my ideal woman, but I was relieved to be having some women after all those men – and these were definitely women. Then I noticed one of them helping the other put something on – it was a huge strap on cock – at least 10 inches long. When she was strapped on she ordered me to sit on her so she could fill my ass. Then one of the other women stood on the bed over my head, with her hairy pussy right in my face. The third girl then mounted my cock. As I thrust up into her pussy, the girl below me thrust further into my ass, while at the same time I was also pushing up with my tongue into the other’s pussy. We continued until I and the two girls came. The girl with the strap on pulled out of me which made me feel so empty after having such a huge thing in me. It was her turn to cum. She sat on my face for me to lick her ass and ordered me to massage her pussy at the same time. She flooded my face with her juices.

As she left I looked up at the clock and realise my hour had now past. Sandy came into the room greeted by applause, which she said was all for me.

It was Sunday morning now and I was back at Sandy’ place. She made me sleep the night covered in cum. I bathed the next morning and felt like a new person. She told me that she hoped I had now got sex with other men and women out of my system and that from now on it was just be the two of us. I smiled and nodded – I finally had the girl for me.

I hope you enjoyed this story - please email me your thoughts and if you want to keep in touch or you have some story ideas for first time gay experiences - let me know.

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5 Comments
AnonymousAnonymousover 4 years ago

I loved both chapters but the second one really made me horny, servicing all those people in front of an audience, mmm I love doing that, do write again soon. X sissy Lucy

AnonymousAnonymousover 8 years ago

Great story. There are many people who don't believe a guy could turn into a cum slut so quickly. I know it can happen because it did with me. I was 48 and had never. Thought of sex with a man. When it happened, I knew I wanted more Andorra. The first night I sucked off four guys then got fucked. I loved it all.

AnonymousAnonymousover 13 years ago
I want what you just had

I loved your story. That is exactly what I want to happen to me. I too want to dress up in sexy women's clothes and get used as a sex toy by numerous men with big cocks. I would love to spend a night or more with a beautiful "chick with a dick" and suck and fuck the whole night long. Please continue this adventure. It's making me really hard !!!

AnonymousAnonymousalmost 16 years ago
this was awsome

I loved that story and would love to read more like it!!!!!

golfjongolfjonalmost 17 years ago
Great and loved every part of it.. sounds wonderfu

I thought this was one of the best stories I have read. I enjoyed it and felt as though I wanted to be that man.. Write more like this one......

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