Helping Hand

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Guy helps his sister in-law explore her fantasy.
1.9k words
4.4
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Part 1 of the 3 part series

Updated 10/26/2022
Created 03/17/2002
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My sister in-law Carolyn recently came from out of town to visit. My wife's birthday was coming up and Carolyn wanted to be here to celebrate the occasion and spend some time with her nephew. She and her husband have been trying to have children of their own for quite some time but have been unsuccessful. I could tell the stress was taking its toll on Carolyn when she arrived. She is an attractive, auburn-haired woman in her late thirties with a pretty face and a nice body. She's just a few years older than my wife but she looked quite a bit older when she showed up. She looked like the weight of the world was on her shoulders.

Carolyn's outlook seemed to do a 180 after she was here for a couple of days and her natural beauty began to shine through as she began to cheer up. One night after my wife had gone to bed, Carolyn and I were up playing some casino games on my PS2 and having some rum and Cokes. We chatted as we played and the subject of her attempting to get pregnant came up. She had been through it all. She'd seen doctors, been through all the tests, and even considered going through expensive in-vitro sessions because nothing had worked.

I told Carolyn about a theory I have had for some time. I thought Carolyn and her husband had been trying too hard and the stress they had been putting on themselves had affected their bodies in a negative way, resulting in their inability to conceive. I surmised they didn't really enjoy the act of making love anymore; they were just going through the motions of trying to make a baby. I told her she needed to relax somehow and she admitted she felt overwhelmed by the pressure she, her husband, and her in-laws have been putting on her to have kids.

I began to tell Carolyn about an idea I had that might help take her mind off the end result of getting pregnant while she and her husband were having sex. I went on to say that as much as she may have been enjoying the sex, I didn't believe she had really been letting herself go. She was too preoccupied with getting pregnant. I told her I would have to show her what I had in mind so she would be convinced it would work, but I didn't tell her what the idea was. Carolyn was unsure of what I had in mind but she was at the end of her rope and was willing to try just about anything. I told Carolyn the only thing I needed her to do was to just relax and trust me. Figuring she had nothing to lose, Carolyn agreed to go along with my plan.

I stood up and asked Carolyn to do the same. She gulped down the last of her drink and unsteadily made it to her feet. Carolyn was wearing a short robe that I untied and pushed back over her shoulders. I could see her full breasts sway through the silky fabric of her nightie as she raised her hands to meekly protest. She was hesitant, not knowing what I was going to do, but I assured her she just needed to trust me.

Carolyn was wearing a satin and lace maroon two-piece nightie. It was fairly modest, nothing wild or see-through, but she looked pretty sexy in it and I could feel my passion begin to swell. I led Carolyn to the sectional couch and sat back in the corner where the couches join. I then placed a bed pillow I had been leaning on while playing the PS2 in front of me, partially for a cushion and partially to cover my growing hard-on. I had Carolyn sit down between my legs with her back to me.

I leaned back against the couch, sitting upright, and had Carolyn lean back against the pillow. I moved her hair to one side, told her to close her eyes, and leaned in to whisper in her ear. In soothing tones I told her to just relax her whole body as I gently ran my hand over her arms and upper legs. I continued whispering warmly in her ear, trying to relax her, as I moved my hands up to her face and slowly traced her features with my fingers. Carolyn told me what I was doing felt very good and that she felt totally relaxed. I continued to run my hands gently over Carolyn's face, arms, shoulders, and legs as I whispered that I would need her to use her imagination for what I had planned. I told her that when she makes love to her husband she needs to let go, to lose herself in the heat of the moment.

"What's your favorite fantasy? What gets you hot just thinking about it," I cooed in her ear. In Carolyn's relaxed state her mind went blank so I began to probe as I continued my soothing actions. "Do you fantasize about making love to a complete stranger?"

"No," she replied. "How about making love to another woman?"

"Not really, it gets my husband off to fantasize about me having sex with another woman but I'm not really into it," answered Carolyn. "How about a threesome," I continued. It must have struck a cord in her because she hesitated, then softly moaned.

"Looks like I finally came up with something you like," I joked. "Does the thought of making love to two men at the same time make you wet," I asked. Carolyn responded with a throaty, "Ooohh yeah...," and now I knew what tact to take with her as I continued to whisper in her ear. "Have you ever made love to two men at the same time before," I asked. "No, but it's always made me hot thinking about it," she responded. "I want you to imagine what it would be like." With that I reached down and took Carolyn's hands in mine and began to guide her hands over her body.

"Four hands moving over your body, touching you all over, caressing you," I purred as I moved her hands to her breasts and cupped her mounds through her nightie. I moved her fingers to massage her breasts, grazing over the stiffening nipples, as I went on. "Two mouths planting soft, wet kisses all over you. Licking you, sucking you, tasting you." Carolyn's breathing was becoming more labored as she got hotter. I left her hands on her breasts and she continued to massage them and I stroked her stomach and legs. "You're completely nude and they are slowly working over your entire body with their hands and mouths. Can you feel it," I asked. "Oooh, yeah," she moaned as she pushed up the top of her nightie so she could play with her bare breasts. I watched as she worked her beautiful exposed nipples, tugging and twisting on her hard pink nubs. My now-raging hard-on strained against the pillow as I wondered if Carolyn could feel it.

I again placed my hands back over Carolyn's, feeling the soft skin of her breasts as I laced my fingers through hers. Our hands massaged her mounds as I breathed hotly on her neck, sending shivers down her body. I took Carolyn's right hand from her breast and guided it slowly down her bare stomach. "Can you feel one of them move between your legs," I ask as I slide our hands under the thin elastic waistband of her lingerie bottom. "You're practically begging him to touch you as his hands near your pussy." Our hands glide over her neatly trimmed pubic mound and I slide our middle fingers down her soaking wet slit. Carolyn is very wet and I can feel her juices covering our fingers as they slide up and down her opening. I guide our fingers in small circles around her swollen clit each time we get to the top. As we make another pass over Carolyn's slit, I push our middle fingers into her pussy and she gasps slightly.

I move her hand back to her clit and remove my hand. I whisper that she needs to tell me what happens next as she massages her clit. "Oh, one of them goes down on me as I suck the other one," she moans. I could tell Carolyn wasn't totally lost in the fantasy yet by the fact that she wasn't too descriptive about what was happening. She also stopped after the brief description. I obviously was going to have to goad her along to get her to totally let go.

I move my fingers to my mouth to moisten them and begin to glide my wet fingers over Carolyn's nipples as I ask, "Does he have a big cock?"

"Mmm...it's sooo big. My hand barely fits around it," she moans. I continue to lead her, "What are you doing to that huge, throbbing cock?"

"I'm running my tongue around the head of it as I stroke it. Then I take it into my mouth and suck on it."

"What happens next?" Carolyn is rubbing her clit rapidly as she speaks. "I suck on his cock as he pushes it into my mouth, then they switch places and I get on my knees to suck the other guy..." she trails off. I pick up the story as she concentrates on her clit.

"And the one with the huge cock moves behind you?"

"Yesss..." she responds. "He rubs the engorged head of his thick cock up and down your wet pussy but doesn't go inside. He begins to tease you, pushing just the tip of it inside. Tell him what you want him to do."

"Ooohhh fuck me. Stick that big dick in my pussy," she moans as she furiously rubs her clit. I continue, "You've got two cocks inside you, one in your mouth and one in your pussy. Suck that guy's hard cock while the other guy fills your pussy from behind with his big dick." With that Carolyn lifts her hips off the couch as she breathlessly cries, "Yes...yes...oh yesssss," and brings herself to orgasm as I tug on her nipples.

Carolyn's orgasm subsides as she collapses back onto the couch. "Oh God, that felt so incredible," Carolyn pants as she tries to catch her breath. I stop massaging her breasts and take her hand from her pussy. I move it up to my face and take her fingers into my mouth one at a time, tasting her juices and sucking them clean. "See, that's what you need to do the next time you're with your husband. Fantasize about something that gets you so hot it takes your mind off making a baby." Carolyn realizes her top is still pushed up and sheepishly pulls it back down. "Seeing as how I just got so lost in the fantasy that I masturbated in front of my brother in-law, I suppose it is possible that your plan might work. Feeling suddenly tired, Carolyn says she needs to get to bed. She turns and leans in to give me a goodnight kiss and I am surprised when she opens her mouth. I reciprocate and we kiss passionately but briefly. Before Carolyn pulls away, she whispers in my ear, "That's for before, that was the most incredible orgasm I've ever had." I watch her ass jiggle through her nightie as she walks away toward the hallway and out of sight.

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