Chapter 1
“Oh how I want him!” I would often think to myself when I saw Dan. Everything about him was perfect. From the cut of his suit to his gorgeous hair, from his laugh to his choice of coffee.
We had been working together at the bank for six weeks, since my transfer from the city. When I first saw him my heart skipped a beat, he was the personification of what I find attractive in a man, tall, slim, well groomed, well dressed. He was handsome without being pretty, I could tell that, unlike other men I had known, he did not spend half an hour in front of a mirror before work every day.
I am not so conceited, however, to believe he was attainable to me. When I look at myself naked in the bathroom, I see a nice 23 year-old female body. My legs are quite shapely and my breasts, though average in size, are perky and free from stretch marks. I am pleased with body, but I am not pretty. Though I do not think myself ugly, I am in not doubts about the unlikeliness of my ever winning a beauty contest. My other great fault is that I have no dress sense. I have tried hard, I watch TV programs and read style magazines, but when it comes to buying clothes for myself, I never seem to get it quite right. Suffice to say, I always saw myself in a league well below Dan.
Chapter 2
I was in the lunch room one day in November, reading a book, when Dan and a few of his friends came in and sat at the table behind mine. Without taking my eyes off the pages, though remembering to turn the page occasionally, I stopped reading to eavesdrop on his conversation. For a while they talked about work, then football and I was beginning to get bored and considering returning to my book, when the topic changed again.
“So are you and Dirty Debbie still together?” The voice was Steve, a friend of Dan’s. I did not know to whom he directed the question, as my back was to everything. But I prayed silently that it would not be Dan who answered. It was not.
“Yeah we are,” Chris, another of the guys, answered. “I’m not going to stay with her, she is a moaning bitch. But I’m going to get a few more dirty nights with her before I get rid of her. Not many girls are up for the things she is, so I’m going to get it while I can”
“They don’t call her Dirty Debbie for nothing!” Steve again this time.
“I’ll tell you what, I’ve never been with a woman like her.” Chris lowered his voice considerably, and I had to strain to make out what he was saying.
“The first time we had sex, she told me to fuck her in the ass, and let me cum in it. She has me rimming her and everything.”
I was not familiar with the word ‘rimming’ and was making a mental note to look it up, when I was given a clear indication of what it might mean by Steve.
“Doesn’t it taste of shit when you do that though?”
“Do you think I would be doing it if it did?” Chris answered. “Anyway, she always showers before she comes to bed so it will be clean.”
They stopped talking for a few moments and ate their food. I was shocked. I could not imagine asking a guy to lick my ass. Certainly I have had men go down on my in the past, and I enjoy it very much, but my ass? I could not imagine such a thing. I was still baffled when Chris spoke again.
“Have any of you ever done that?” He was answered in grunts which I took to be all nos.
“I have done anal with a girl, but only after a week of begging.” The voice was Craig, a rather fat guy who I did not like. I was just about to scoff to myself, when I heard Dan’s voice for the first time.
“Craig, you can’t beg a girl to do anal! If she said no for a week then finally agreed, she probably just gave in. She probably didn’t want to do it at all.”
“I don’t care what she wants Dan! I care about what I want.”
“You’re a dick Craig,” Dan answered, my love for him soaring. “I have always wanted to try anal, but I would never ask for it. It has to be asked for, like Dirty Debbie did. If I thought a girl wasn’t liking it, I wouldn’t do it.”
“I’ll be done with Dirty Debbie soon,” Chris piped in again. “If you don’t mind sloppy seconds.”
“Mate, if you think you’re the first person who’s been there, you’re dumber than you look,” Dan said with half a mouthful of sandwich. At that point, Steve started talking about his new mobile phone, and the conversation switched to that. I closed my book and left the lunch room.
Chapter 3
That evening, as I showered, I ran a soapy finger over my asshole. I had done this all my life as part of cleaning of course, but this time I tried to imagine my fingertip as Dan’s tongue. The sensation was quite nice, and as I became aroused, my other hand made it’s way to my pussy without my knowing it. Soon I was rubbing both my clitoris and my asshole simultaneously, and it wasn’t long before I came.
Panting, I came to my senses and realised that I had just experienced my first anal stimulation. I can quite honestly say that I had enjoyed it.
A little later I was in bed. I set my alarm for the morning, and composed myself for sleep. But sleep would not come. I could not help but think that if I had enjoyed my anus being stimulated, would I also enjoy actual penetration? Without really deciding to, I switched on my bedside lamp, and in the drawer below it I fumbled for my vibrator. When I found it, I looked at it, imagining how it might feel in my ass. It was not a long vibrator, nor very wide. I decided to try it.
I lay back down in my bed, turned the vibrator on, and put it to my clitoris. It was still sensitive from my orgasm in the shower, so soon I was aroused and wet. Taking a breath, I rubbed the end of the vibrator around my pussy, moistening the end. When satisfied, I moved it down to my asshole. Again the sensation against my anus was quite pleasant, but when I pushed the end in and felt my soft skin stretch, I found myself wincing. It was not comfortable.
I removed the vibrator and used my fingers to transfer some wetness from my pussy to my ass, then tried again. I was surprised to find that my ass allowed it in quite easily. But I must be honest, I didn’t like the feeling.
Chapter 4
They were looking. I had done it. They were all looking at me. It was the Christmas Party, a week before Christmas Day. I had spent a lot of money on this gamble, but it was working. My hair had been done in a salon, it normally costs me about £25, but I had paid nearly £100 for this one. It was totally different to what it had been. I had always been a natural blonde, but they had put subtle highlights in it and changed the style completely. I had also had my make-up professionally done. I had found that I could be made to look reasonably pretty with the right knowledge, and I was sure I could replicate the look myself in future. I had side-stepped the problem of my inept dress sense, by using common sense. For the first time in my life I had gone to a designer store. There, I bought, with advice from the store assistant, a dress which cost as much a half my month’s rent.
But it was working! That was the important bit! It was working! All of the men were looking at me, looking away, then looking straight back. The dress emphasised my shapely legs and my bum. My back was almost nude and there was a divide between my breasts, showing that I wore no bra. When I saw, no, felt Dan’s eyes caress me, my heart fluttered. Then it almost stopped completely, BECAUSE HE WAS COMING OVER!
I will not write what was said between us, not because it is not important or interesting, but because I hardly remember it myself. I remember him knowing my name, which I did not expect. I remember him telling me how wonderful I looked, and I, returning the compliment. The fact that I had been drinking a lot did not help either. I had had a large glass of wine before coming out, and was drinking double Vodkas with Coke. I was more than a little drunk when what I had hoped so much would happen, did. Dan gave me a sign. A little one, but enough for me to be sure. Someone was trying to get past behind me, and Dan put his hand on my waist to gently move me to one side. His hand was there just a moment longer than was necessary. I knew then, that if I went through with my plan, there was a chance it might work. I pressed my body against his, feeling my breasts flatten against his chest. I raised my chin to his face and he stooped his to his mine. He was a wonderful kisser, and as soon as the kiss broke, I whispered in his ear.
“I want you Dan, tonight.” He was startled, I could see it, but like the true gent he was, he did not immediately jump at the opportunity, but kissed me again.
Soon we were in a cab, heading to my flat.
Soon we were in my flat.
Soon we were kissing.
My dress was off, I was naked kissing him. I could feel his cock, fully erect, straining to get out of his jeans. I groped it with both hands.
“This guy wants some attention I see,” I whispered in his ear in my huskiest voice.
I dropped to my knees and unbuttoned his jeans, pulling them down. He was wearing black boxer shorts, and his cock flicked up once it was free from the restraint of his jeans. I yanked down the and took his cock in my mouth. Voraciously I sucked it, tasting the first few drops of his pre-cum from the tip.
I looked up, still sucking. He had taken off his shirt, so all he wore was the pair of boxers at his knees. I stopped sucking and stood up, stroking his cock with one hand. He kissed me, and as he did, he ran both of his hands down my back to my ass. He squeezed and pulled at my ass cheeks, before one hand found its way between them to my pussy. I parted my thighs slightly to give him better access. He rubbed my labia gently, and probed my opening only slightly. I quivered with pleasure, perhaps showing even more than I felt in my eagerness to please him. Suddenly he picked me up in his arms. Even though I am only 120 pounds, he lifted me with such ease that I was surprised. He lay me down on my own couch, but with my buttocks on the arm, and my legs hanging over it. Then he dropped to his knees, and gave me the best oral sex I had ever had. I am not sure how long he did it for, but I came three times, the last so hard that I cried out. I had never been with a man who seemed to enjoy giving oral so much.
Finally though, he spoke. “Do you have any condoms? I don’t have any.”
“No,” I replied, “But I am on the pill, so it is OK.”
“Sure?” Dan asked. How much more could this man impress me? Normally guys hearing that just stick it straight in. Not Dan though.
“I’m sure, and if you don’t fuck me now, I’ll cut it off!”
He stood up then, and guided his cock into my pussy. I was so wet that its full length instantly slid in. The position was perfect, my body was on display to him, my legs wide open so he could see his cock thumping into me, and I could see his lovely toned torso working. I was so turned on that I started to cum immediately, and as I did, Dan put a thumb on my clit and started rubbing. I then learned what a multiple orgasm is. Wave after wave rocked me to my soul, I cried tears of pleasure and I am sure every neighbour must have heard me.
Dan then flipped me over, into doggy style, and fucked me that way. I had hoped he would do that, it was time for my plan. I flattened myself as much as I could, so my ass cheeks were tight and round and spread, and my asshole was clearly visible to him.
“Will you fuck my ass Dan?” I asked. It was not my choice of words, left to myself I would have said, “Shall we do anal?” or something like that, but I had been watching anal porn in preperation for this, and that is what they always said.
He stopped fucking me. “You want me to fuck your ass?”
“That’s what I said, wasn’t it?” As I said this, I reached down to my ass, and started teasing my asshole with my finger.
“Erm, do you have any lube or anything? I don’t want to hurt you.” I was ready for this too.
“Lick it first, get it wet for me.”
He did not need further encouragement. It was even better than I imagined, He teased and probed my ass with his tongue, while I reached between my thighs to rub my clit, and soon I was coming again. As I did, Dan stood up and put the end of his cock up against my anus.
“Are you ready?” He asked.
“Fuck me!” I yelled.
Slowly, he pushed the tip into my ass, and the familiar feelings came back to me. I had practiced this moment many times with my vibrator, but still not managed to enjoy it. As I felt his cock slowly fill my asshole, I simulated pleasure I moaned and groaned, as I had heard the pornstars do. In truth, there was some pain and it was tremendously uncomfortable. As I felt his pelvis make contact with the back of my legs and buttocks, I pulled away, so that he almost came back out, and at the last moment thrusted back in again, taking him fully in my asshole.
“Dan!” I cried, “Fuck me, fuck me hard!”
He grabbed my hips and started thrusting hard into my ass. It was so uncomfortable, so painful, but I hid it. I moaned with pleasure, I told him how good it felt, but I didn’t like it. This was my plan. I got my fantasy, at the cost of giving him his, and I was not finished. I moved forward, causing him to slide out of my ass, then turned around and took his full length in my mouth. This was something I had seen the pornstars do. When I first saw it, I could not believe that a woman could suck a cock straight from her ass without gagging, but then I saw more and more women do it without even flinching. I had read up on it and found out that, with proper preperation, it could be done safely and is not even particularly unhygienic. I had visited a clinic that afternoon and had my first enema. I was as prepared as was possible. However, as I did it, I was still very very anxious that I would gag. I did not, his cock tasted odd, but not like what I was afraid of. I could do it without any particular displeasure.
Dan however was shocked.
“Wow!” He said “You are one dirty girl!” I could see he was not actually put off though.
“The dirtiest!” I replied, “Now put your cock back up my arse so I can suck it again.”
“Lets go to the bedroom,” Dan suggested. “I want to hold you while I fuck you.”
In the bedroom Dan lay me down with my back to his front, the Spoons position. Then he gently guided his cock back into my asshole, and fucked me further. Again, I simulated the pleasure, making the noises I thought he would like to hear, but I still could not find it pleasurable.
Until.
After a few minutes of the Spoons position, Dan reached round and began rubbing my clit again. All of a sudden, once my mind was not so occupied faking pleasure I started to feel some. As he rubbed, I found that my ass relaxed. Then it was more than relaxed, it was eager. I felt the second multiple orgasm of my life building. It was coming more slowly than the first, so I had time to anticipate it.
“Dan,” I panted, “Don’t stop, fuck me harder! Yeah! Faster! Oh God, I’m going to cum so hard!”
Dan thrusted harder into my ass, and his fingers kept a perfect rhythm on my clit. I came. I came like I never have before, and as I did I felt Dan’s cock begin to throb in my ass, and I knew he was coming too.
“Cum in my arse Dan fill my fucking arse!”
Dan cried out and I felt the jets of hot cum spurt into my ass. I was truly loving it, the perversity of it, the dirtiness! I knew I had to suck his cock again.
When he withdrew his cock, he was in that far away place men go after they ejaculate, and he rolled on to his back. I too rolled over and took his cock in my mouth again. It tasted this time of his spunk, and as I sucked, I thought to myself.
“Amy, I could get used to this.”
Via: https://www.lushstories.com/stories/anal/the-price-of-desire