Trying Something New

It was Saturday morning, Kyle, a friend from work, and I was finishing a round of golf. Pulling my ball out of the 17th hole, the conversation turned to sex. He started telling me about all the things he and his wife have done. He ended by saying they often have anal sex and his wife enjoys it.

Knowing his wife, Kathy, I found it hard to believe. Kathy is 4'10" and petit. It was hard to visualize her having anal sex without screaming or clawing the ceiling.

All through lunch and on the drive home I couldn't stop thinking about them having anal sex.

After nine years of marriage, my sex life is still pretty active. It's mostly the missionary position with a little oral mixed in once in a while. There may not be a lot of extra pizzazz, but I'm satisfied. I think she is too.

I spent the rest of the afternoon doing some odd jobs around the house, While my wife, Lisa did her weekly cleaning. We had barbecued burgers for dinner. After cleaning up, we sat down to watch television. With nothing on, but reality shows, we both decided to read. Between articles of my magazine, my mind wandered back to what Kyle said earlier.

I laid my magazine down and looked across the room.

I asked Lisa,

"Have you ever had anal sex?"

With a puzzled look, she said,

"No. Why do you ask?"

In a sarcastic tone, she asked,

"What are you reading?"

At the risk of having Lisa think different about Kyle and Kathy, I told her about our conversation on the golf course. At the end of my monologue of Kyle's revelation, Lisa asked,

"Have you ever had anal sex?"

"No. I have often wondered would it would be like, but I don't know."

Forgetting my train of thought I kind of left my answer incomplete.

Putting her book on the end table, Lisa picked up her iced tea. In a tone of curiosity, I asked her,

"Have you ever thought about it?"

Setting her glass down after taking a sip, she answered,

"I had a girlfriend in college who said anal sex was great. She also said her and her boyfriend had anal sex when she was on her period and they were horny. As for me I always figured it was painful. No one has ever come out and ask me to try it and I didn't volunteer."

CSI Miami came on. We both got into the show and the conversation died. The show was interesting and entertaining. all during the show I kept thinking about our conversation and wondering what Lisa was thinking.

Sliding between the sheets, I started admiring my Lisa's beautiful body. Wearing just a pair of hip hugger panties, my eyes started roaming down her body. At thirty eight, her large round breasts have started to sag. working a full time job, she hasn't really had time to work out. She has gained a few extra pounds around her stomach, hips and butt.

I think the extra pounds adds to her beauty. She thinks she's unatractive and will not wear a bathing suit. we leaned close for a hug. After a long kiss, she said,

"After the earlier convesation, I'll bet you have been thinking about experimenting."

In a tone of excitement, I said,

"Yeah I guess I've thought about it."

After several more kisses and fondling her brests, Lisa said,

"I'll let you try it under one condition. You have got to give me a chance to give it to you in the ass with my vibrator, first.

Lisa got up. Getting a small vibrator out of her dresser and another larger one from her nightstand, she left the room. coming back with some baby oil, she said,

"How bad do you want to try this?"

Throwing the covers off me, I said,

"I'll try anything once, twice if it don't hurt."

Lisa crawled into bed next to me. Turning on the small vibrator, she started to grin. It was a look of control, total control. The vibrator started to hum. The noise was loud enough to make it interesting. The smaller one was five inches long and an inch around. With the little one still on, she leaned over and started kissing me. She let go of the vibrator. It rolled down my hip, landing near my cock. It started vibrating my cock and balls.

She broke off the kiss and rolled me on my side. Turning on the bigger vibrator, she laid it down. Pouring baby oil over both of them, sh picked up the smaller one. As she touched it to my ass, I started to cringe. Realizing my aprehenson, she reached for my cock to help me relax. Sliding it in my ass, the vibrations were tingling my sphincter.

she slid it in faster, while playing with my cock ad balls with her other hand. With a plop, she pulled it out. Grabbing the bigger one, I cringed again. It was seven or eight inches long and two inches around.

she slid it in my ass. It had a harder vibration. At first it hurt. The more she moved it, the more I got used to it. She reached for my cock and I almost burst. Sensing I was close to cumming, she pulled it out. grabbing the baby oil, she said,

"Here's your chance."

Lisa poured the baby oil in my hands then rubbed some on my cock. rolling on to her side, she said,

"Start with a finger."

I slid one finger in slowly, stopping a couple of times. I could tell she was getting used to it. I went with two fingers. I started moving faster. I reached a hand around and started to caress her breasts. Pulling my fingers out, I moved closer. With the tip of my cock at the opening, I slowly entered. I stopped with just the head inside. I started again. As we got going, Lisa started meeting my every thrust. Since I was so close earlier, it didn't take long before I erupted. I pulled out and shot my cum all over her back, butt and hip. We both laid down in a sweaty, oily cum filled mess. We talked a little about what happened and fell asleep.

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Submitted by : Anonymous
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Disclaimer: All posted stories include descriptions of sex scenes that could cause offence to some people. Please do not read this story if you are offended by perverse sexual material, or if you are under the legal age of consent for your own country. These stories are pure fiction and are not based on anyone living or deceased.

But it was getting late, and sooner or later it would be time to leave.
Chris went to the bar to order a final round of drinks. Watching him walk across the room, Amy was suddenly aware of how attractive he was, and how good he made her feel. she could almost imagine those big gentle hands holding her, those soft lips against her skin.

He turned and looked back at her and she blushed deeply at her own thoughts. How could she think like that They had only just met! But as he returned with their drinks she found herself unwillingly drawn to sit closer to him. wanting to touch him, she reached out and put her hand tentatively on his knee, all the time ashamed of her own boldness but unable to stop the nervous heat building inside her.

He placed a hand over hers and slowly moved to kiss her. Gently at first and then his tongue just gently stroking her lower lip, pushing her lips apart. She leaned into him, feeling her body responding to his touch as he pulled her towards him and kissed her more deeply.


Shaking slightly she pulled away, reaching for her drink quickly to try to calm her nerves. Common sense was telling her to leave, now, but her body was telling a different story. she felt so out of control, terrified at how far she could let it go and yet wanting it so badly. He was talking to her, asking if they could leave, his voice softer and suddenly breathless. He took her hand and led her from the bar, and she knew she would not turn him down.

In the taxi they kissed again, his hand stroking her thigh, and sliding slowly up under her skirt. She could feel the heat building there and the wetness, as his fingers stroked her through the material of her underwear. He ran his fingers along the edge of the fabric and gently slipped his forefinger underneath. He felt how wet she was and gently slid his finger over her clitoris. She pulled away from the kiss, gasping and shivering at his touch, her eyes showed how much she needed him, but she also looked fearful, overpowered by how fast thing were moving.

"relax," he whispered softly, reaching to stroke her hair back from her face, "it's alright."


At his house she knew she should try to go, common sense was screaming at her, telling her you don't know this man. But still she allowed herself to be led inside. Wordlessly he led her straight upstairs and sat on the edge of his large bed. He held on to her wrist and pulled her to stand in front of him.

Ashamed of herself but unable to resist Amy bent to kiss him again on the lips and neck as his hands reached for the buttons on her blouse. His fingers were warm on her skin, stroking her breasts softly and then up over her shoulders to slide the blouse down her back and onto the floor. Chris stroked up and down her back gently with one hand, the other holding her waist, and then unclasped her bra. All at once he was kissing her stomach, unbuttoning her skirt and kissing lower as skirt and thong fell to the ground. She shivered at being so exposed in front of this man who had revealed nothing of himself to her. Amy wanted to unbutton his shirt but he pushed her hands away.

"no, not yet." He whispered, standing.

Holding her shoulders he pushed her down onto the bed.

Shaking all over she lay, under his gaze, unsure what to do next. He watched her closely. It was almost uncomfortable, and yet she was so aroused by her vulnerability. She wanted to be touched again but was unsure how to ask.

Chris placed a hand on each thigh and slowly parted them wide. He was looking closely at her warm, wet lips, and reached to touch them, his two fingers pressing them apart to reveal everything to his gaze. He stroked her there. Up and down over her clitoris and gently teasing the entrance of her sex. Pushing a little way inside and making her gasp with pleasure. She wanted him inside her, raised her hips to meet his hand, to take his fingers deeper. But he pulled away, watching her quick breathing and her flushed face.

As he began to undress himself she sat up to unbutton his fly. He pushed her back,

"No, lie still, Amy." and slowly revealed himself. He was hard and erect and the sight made her want him all the more, but any attempts she made to touch him were pushed gently away.

"Lie still, Amy. Relax. I want to touch you."

He began stroking her again, but this time his fingers were slipping past her vagina, over her perenium. It felt strange and good to be touched there, and when he bent to lick this sensitive skin it sent new waves of pleasure through her. she had never been touched like this before. The warmth and wetness of the tongue was turning her on more than she believed possible.

Chris stopped, and pulled her into a sitting position. he looked deep into her eyes, seeing the way she was feeling.

"Turn over, onto your knees, Amy." He whispered, and she shakily did as he asked.

The tongue was back stroking and teasing her again, and she felt him part her legs further to better reach her lips.Then she felt him move higher and his soft tongue was gently running over her anus and around it. His hand slipped between her legs and stroked her there and she began to moan softly with pleasure.

Chris pulled away from her, and reached into a bedside drawer.

The feel of his lubricated finger on her anus was a shock to Amy and she flinched in sudden fear. "No!" This was something she had always been afraid to try, sure that it would be unbearably painful.

"Relax sweetheart."

He pulled her hips back towards him and began again his gentle massage. This time holding her near him. His fingers pressed a little harder on the tight anus, feeling how tense she was.

"No, I don't want that." Amy was so sure it would hurt her, but the feelings produced by his soft stroking were becoming far better than she had imagined.

"It's alright. Please just relax." He continued to slide the slippery finger over her.

She reached forward and hugged a pillow to her, burying her face in it to stifle the soft, high gasps of pleasure she could not help but make. The finger gently pushed into her. So slowly she barely noticed her muscles relaxing around it. Just the tip at first, pressing into her and then just stroking over the hole once again. Gradually she became able to take more of it, as he slowly pushed deeper each time.

Chris continued to hold her still, and gently relaxed and stretched her anus until he could insert another finger. Amy was shaking and sobing with the intensity of it. It was hurting a little but in a way that was part of the pleasure, she was giving to him something she had never given another man. Her hand strayed to her clit and she stroked it softly as she felt Chris gently open his fingers and stretch her further. He knelt on the bed behind her and slowly removed his hand.

Taking the lubricant he slowly rubbed some more into her and then onto himself.

"Just relax." He whispered to her as he pressed against her. She could feel it there, pressing up against her and so slowly sliding a little way in. The size made her gasp and flinch in pain.

"Please, stop" she sobbed.

He stopped pushing into her but did not remove his penis. Instead he gently rubbed her neck to relax her, and bent to kiss her shoulder.

"Just stay still and trust me, please." He pleaded with her. Then began to push again. Slowly, he could feel her giving in to him, he slid deeper into her and heard her gasp, "it hurts, Please!" but still he pushed deeper, watching hungrily as she was stretched around him, enjoying the control he had over her. He began to move within her slowly, while still she stroked her clitoris, sobbing into the pillow.

Gently at first and then harder he thrust as he felt her become accustomed to this new feeling. She began to push back into him, pushing so that he would go deeper still inside her. With each thrust she cried out, at first with pain. He was stretching her and filling her so completely, is felt as though she could take no more and yet she wanted him so much.

Chris could see a hint of blood as their lovemaking grew more intense, he could see how he was opening her wide to take all of him and hear her panting and crying as she struggled with the size of him.

But Amy was aroused too. The feeling of being used in this way was turning her on so much, despite the pain, she pushed back again and again wanting more of him inside. He moved faster and she clutched at the pillow, stifling her screams as she came hard and out of control.

He held her tight as he came deep inside her, feeling her shaking and crying from the strongest orgasm she had ever felt. She collapsed in his arms crying. Chris held her until she calmed down, stroking her and whispering to her as she fell asleep, exhausted.