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Sandy Liberates Me Ch. 1

By: nowiamhere



I have been committed to my career for so long now that I have almost forgotten about what a social life is. Sure I thought about sex and managed to pick up a few women from time to time, but nothing too serious. I was your typical straight workaholic type – for the record, I am in my 30s and with an average slender build.

Anyway, I escaped from work at 8pm knowing I had an hour to make it to the shops and buy a new pair of pants I was in desperate need of. I had been into 3 shops and it was now right on 9pm and I had not found what I was looking for. I was looking through the window of the next shop – they still looked open, so I wondered in. I browsed through quickly and grabbed a couple of pairs to try on. The sales assistant was taller than me with long legs, a beautiful smile, blonde hair and deep hazel eyes. If I wasn’t in such a hurry, I would have stopped for a little longer to soak in her beauty. I asked if I had time to try them on. She said “not a problem, but I am going to lock the front door as we are now closed.”

The first pair fitted perfectly, and so I politely yelled out to her “that I was going to take the first pair.” Before I could finish the sentence, she had the curtain open. “mmm they do look good…do you want to try the others on as well?” She stood there watching closely as I tried on the second pair. I felt a little strange at first, but then I thought, well this is kind of a professional setting so it must be alright. But then something happened which definitely changed my mind. She brushed her hand against the outline of my cock and moaned. I looked at her and smiled. That was it seems all she needed. She pulled the curtain closed in the change room and began to suck on the outline of my cock which was growing harder by the second. She looked at me with her sexy eyes and pulled the waistband down. Then she engulfed my cock in one go. I have 8 inches cut – average thickness. Every inch was in her hot wet mouth and she sucked me hard. She pulled off for only a second to tell me to cum in her mouth fast. I didn’t need much encouragement as she was driving me crazy. Here I was with one of the sexiest women I had ever seen giving me blowjob. Within a couple of minutes I was filling her mouth with my juices. She did not miss a drop. She then licked her lips and told me her name was Sandy and that I should get dressed and join her for a drink.

I paid for the pants without a word being spoken. She looked at my card to get my name (Kevin) and whispered for me to follow her to her city apartment.

Sandy lived on the 20th floor of a city block. The views were spectacular at night with all the city lights below. She told me to make myself comfortable on the leather lounge while she changed and made us a drink. When Sandy walked back in the room my cock was immediately back at full attention. She was dressed in a sexy teddy which barely concealed her perfect looking breasts. She was carrying just one drink with two straws. She straddled me as we sipped on the cocktail. I am not sure what it was – but I did not really care at that point. It was making me feel a little giddy, in a happy kind of way. Her ass was rubbing against my hardening cock. We kissed long and passionately for several minutes before she invited me into her bedroom. 

She removed my clothing piece by piece, licking my nipples and down my chest as she did it. I was standing there naked with just the moonlight to see the silhouette of this gorgeous woman before me. She slipped her teddy off to give me the first real look at those pert breasts. She was still wearing lace panties as she pushed me down on her bed, which had a burgundy silk sheet draped over it. I licked and sucked on those nipples as she fed them to me one by one. 

“Do you like my breasts – you are the first one to touch them since I had the implants.” Asked Sandy. “They are perfect” I muttered as I kissed her soft lips again.

“Kevin, have you ever had anal sex before?” I shook my head. “It’s such a sexual and personal thing – I want to feel you in my ass. Will you fuck my ass Kevin?”

Her voice was so sexy, I could not resist her. “I’d love to try anything with you.” 

I lay on my back on the bed. My cock was as hard as ever. When it is erect it curves back up slightly. So as I look down I could see the tip clearly. Sandy returned from the bathroom with her panties on as she straddled me. She pulled the g-string to one side as she placed my cock at the entrance of her hole. She had obviously applied some lotion while she was in the bathroom. My cock started to slide into her. It was an amazing feeling as she moved her hips from side to side. Her ass was tight and firm around my cock. Her tits were in my face as I helped her move up and down on my shaft. Each time she felt me get close she slowed down so we could fuck some more. Finally I could not take any more and I exploded deep inside her ass. She clenched her cheeks together to drain the last of the cum from me.

Then something happened which really took me off guard. Sandy fell forward to rest on my chest. There was something hard between her legs. I did not pay a huge amount of attention to it as after all I had just had the best fuck of my life with a gorgeous woman.

After a while Sandy asked me to close my eyes as she stood up off me. I could hear her remove her g-string and felt her crawl back on to the bed. Her knees were resting on either side of my upper body. She then asked me to open my eyes. As I glanced into her eyes she encouraged me to look down. I could not believe what I saw. In Sandy’s hands was a cock, and it was not mine.

“Shhh – don’t be angry. I could have let you go and never told you my secret. But I wanted you to have the chance to experience all I have to offer as I have never been with someone like you and felt so much sexual energy before.”

“I I I I …” was all I could get out.

“Try it – it can be our secret.” Said Sandy.

I tried to open my mouth to say something else, but Sandy had leaned forward and my open mouth was greeted with her cock. That sounds so strange. But she looked so much like a woman except for this 5 inch cock. Perhaps I should have registered when she kept her g-string on and wanted me to fuck her ass, but she must have had her cock tucked away – because I don’t remember seeing a bulge. I had no time to think of that now. I had a cock in my mouth.

She teased my lips with it, before then pushing it all the way in my mouth. She urged me to suck hard. Sandy was horny alright…she was oozing pre-cum and her cock was throbbing. I could feel the pressure start to build very quickly. Then it happened. Cum started to fill my mouth and dribble out the corners. She emptied her load into my mouth and then onto my face. Then Sandy leaned forward and kissed me. We shared her juices.

As she broke the kiss away she lay beside me looking at me with her sexy eyes. I was still thinking of her as a woman despite the fact that I had just had her cock in my mouth. I was confused. I was not gay. I had never even contemplated being with a guy before, yet here I was in bed with a sort of guy.

Sandy said “you are a fantastic lover. I hope you don’t think I tricked you. I know my looks are deceiving. But have you never been with a guy before at all?” I shook my head.

“I will understand if you want to leave and forget this ever happened and there will be no hard feelings. But I want you to know that I would like you to stay. I want you to experience all I have to offer.”

I was captivated by Sandy’s beauty and by the sexual chemistry. I was trying to justify the idea of being with a guy by thinking about being with a person who I considered beautiful and sexy rather than looking at the sexual activity itself. I was curious too. I wanted to stay.

I leaned over and kissed Sandy lightly on the lips. For the first time I felt another cock rubbing against my own. As I moved down to kiss her breasts and suck on her nipples, I felt her hardening again. She was so excited by my decision to stay.

Sandy stood up on the bed in front of me. I looked straight up taking in every part of this extraordinary body. Looking at the top half, I could not believe what was below. My eyes were fixated on her cock, as she grabbed both my legs and pulled them over her shoulders. “I want to be inside you,” she said.

It was probably a good thing that I did not have time to take in what she had just said. It was one thing to have tasted a cock and another all together to have one shoved inside me. That was something I had definitely never considered until just now. Sandy had already smeared her cum in my ass earlier so I was wet and loose as suddenly her cock thrust at my entrance. It pushed deep inside in one swift motion. I let out a yelp in pain, but she continued with her slow thrusts. After a few minutes the pain had gone and I was yearning for each thrust. Her cock was buried deep in my ass now and I was begging her to cum. She filled my ass with her juices until I felt them leaking out down my leg. I had never experienced anything like it before. 

Sandy Liberates Me Ch. 2



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.