A Little Help From a Friend

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Widowed man gets a visit from wife's best friend.
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Part 1 of the 3 part series

Updated 06/08/2023
Created 08/28/2016
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I was in the living room reading the paper when I heard the door to the garage open, then slam.

"Hi Tom!!" It was my friend Kelly's cheery voice. I got up to greet her, giving her a kiss and a long hug, taking the opportunity to run my fingers through her hair.

Kelly and my wife had been best friends, though she and her husband Walter were really friends to us both, and we had often gone to dinner or other events together during the previous ten years. Kelly had taken it upon herself to look after me since my wife had passed away about four months earlier, dropping food off and helping me with some of the other aspects of moving on after losing someone.

I'm pretty independent, and normally would be brushing off the assistance, but the truth was, I liked Kelly. No, I adored Kelly. She had just turned 73-I'm 59-but has a good outlook on life, and she's a lot of fun to be with. She has a pretty smile, and I love the way her blue eyes light up. Unlike a lot of women her age, she has not cut her hair, and her chestnut locks cascade down over her shoulders to about midway down her back. While some might consider her not all that attractive, I didn't mind the bit of a belly, and I really do like her chunky hips and thick thighs, and the way she often would wear tops that showed off her grapefruit size tits. She's really cute in a grandmotherly kind of way. We'd always been flirty, and we have an easy comfort with each other. We'd never laid a hand on each other, except for a hug when meeting or parting, though I suspect our spouses thought we had a crush on each other.

Today, Kelly had on a pair of denim shorts and a wrap top that crossed over itself just below her bust. The top was a little loose, but not enough that she was falling out of it. From the way she was bouncing as she walked through the kitchen, it appeared she was not wearing a bra, and it sure didn't feel like it when I hugged her.

"I brought you some chicken enchiladas," she said, opening the fridge. I enjoyed her cooking, and her enchiladas were always a tasty treat.

"Thanks," I said, clearing some space for the pan. "I love these things. It won't take me long to finish the whole pan."

"Last time I brought these over, you said you'd make me some brownies," said Kelly, teasing about a prior promise. She loved my brownies-not that they were anything special, just Duncan Hines out of the box. Like me, she loves them fudgy, and any time I made them, I'd make sure she had a few extra to take home.

"You doing anything the next hour and a half or so?? I'll make some up now. Just think, hot, gooey, fudgy brownies to take home."

"I'm not in a hurry, and you know how I love chocolate," said Kelly, smiling. "What can I do to help??"

"Reach down into that cabinet and pull out the large glass pan," I said, pointing to one of the lower cabinets. Kelly leaned to open the door and reach in. I was not thinking about her top, but when she leaned forward, my suspicion about her lack of a bra was confirmed, as I could see her left breast swinging free. This was a new thing, as she had always worn one in the past, and I often got a glimpse of a pretty bra when we'd all be out together. She handed me the pan, and I pulled the mix out of the pantry. We got the rest of the ingredients together, and got started.

Kelly was helpful, and we worked well together, moving around each other easily, gently guiding each other with a hand on a shoulder or waist. Unlike in the past, now our touches lingered, Kelly leaving her hand on me, and I doing the same. I pulled her close to me a couple of times. She'd briefly lay her head on my shoulder when I did that, and I'd kiss her hair. I'd occasionally done that when we were out if our spouses were not looking; Kelly had a way of putting her arm around me, knowing I'd react by pulling her close and kissing the top of her head. Now that we were alone, we took advantage of the fact that we didn't have to sneak it. Sometimes when I'd lean to kiss her, she'd look up and meet my lips with hers in a short kiss. This was new. We'd always been flirty with each other, but today, Kelly seemed quite playful. As we finished and put the brownies in the oven, I again hugged her, leaning down to kiss her hair, as I had done many times. She looked up as l leaned over, her lips meeting mine. We shared a short kiss, then another, slightly longer.

"Now you see how the magic happens, not that there's much to it," I said as we stood facing each other.

"I love how fudgy and smooth they are," said Kelly, looking up at me. "And I think we have plenty of magic."

I smiled at her a moment. Was she really coming on to me?? "You see how I do it," I said, trying to keep things from getting out of control. "Just make sure all the mix is blended, and stir til they're really smooth."

Kelly laughed. "Well, they always seem like magic to me." She looked up at me again, this time with a look in her eyes I had not seen before. "Being with you today has been like magic," she said, standing up on tip toes and giving me a slightly lingering kiss. As she kissed me, she was toying with the button that was the highest one I had buttoned on my shirt.

"Yes it has, and keeps getting more magical," I said, figuring, what the hell, go with it, let's see where this leads.

"I know it's been several months since Dee passed, and I thought, as a friendly gesture, I could give you some, well, relief."

I looked at Kelly a moment. "Kelly, you know I've had a crush on you for years. If this is a serious offer, I'm not going to turn you down."

Kelly smiled, undoing my button, and playing her fingers in the thick hair on my chest. "I knew you were fond of me, and truth be told, I didn't mind the attention. I've had something of a crush on you too. I used to live for the days we'd all be out, and you'd hug me and kiss the top of my head. So yes, I'm quite serious."

"How are you going to explain this to Walter??" I asked.

"He's OK with it." Kelly undid another button, now playing her hand on my chest.

"Really??" Walter was a good guy, and we got along well. He didn't seem the type to share his wife, despite the running jokes about putting her to work, or trading her in for a new model.

"Actually, it was his idea." I gave Kelly a curious look. "As you know, he's had some health issues in recent years."

This was true. He'd been fighting emphysema for as long as we'd known him, and it was now affecting his day to day life in a more significant way than it had even a couple of years prior. Kelly and Walter had never discussed the intimate details of their home life, though I got the impression Kelly liked a good roll in the hay. She had made comments on more than one occasion that she was never a student in her school days, but enjoyed the attention she got from the boys.

"He's been feeling bad about not being able to take care of me as well as he has in the past," said Kelly, looking at me wistfully. "And he knows that it's been several months since you lost Dee. He thought if I came over to see you, we could spend some time together. You'd take care of me, I'd take care of you, and he'd feel good knowing that I was with someone he trusted, which would be a relief to him." Kelly stood on her toes and kissed me.

"How do you feel about this??" I asked.

Kelly smiled and looked up at me, a gleam in her eyes. "I think it's great. How often does a married woman get a 'hall pass' to make love with her crush??" She kissed me again. This time, she lingered, her right hand flat on my chest, her left reaching around me to pull me close. I leaned into her, taking her in my arms, savoring the kiss I'd thought about for years. Our lips parted, Kelly sinking back to the floor, looking up at me. The look in her eyes was love, desire, and apprehension all at once. I wasn't sure at this point if she was going to stay on the course she had started, or bolt. Yet, there was a look in her eyes I had not seen before. I caressed her cheek, then played my fingers through her hair. I leaned down to kiss her, again feeling the softness of her lips as we joined. Her tongue darted in and out of my mouth, wrestling with mine in a long, deep kiss that left no doubts as to our feelings.

We pulled away from our kiss, looking deep into each other's eyes. I took her by the hand. "Come on," I said, leading her toward the sofa. We sat and continued to make out, Kelly opening more of my shirt. She seemed fascinated by my chest, playing in the hair and rubbing me all around. "You really like playing in there, don't you??" I asked playfully.

"I love a hairy chest, but Walter hardly has a hair on him," said Kelly, now working her fingers through the hair more gently. "I'm really enjoying this. Whenever we went out and you'd wear a button down shirt, it was all I could do not to climb into it, especially since you always had it open enough to show off your chest so well. I'd imagine what it would be like to be doing what I'm doing right now."

I returned the gesture, playing first with Kelly's breasts through her top as we kissed, making her nipples poke through the thin material. Then I reached in, holding her right tit, playing with the nipple, and pulling it out of her wrap style top. Now that I had one breast out, I kissed down Kelly's neck, making her squirm, then latched onto the nipple, swirling my tongue on it. Kelly sighed as I gave it my full attention, and I soon had her nipple standing tall. I moved back up Kelly's chest and neck, kissing her again, pulling her left breast from its confinement.

"Your chest it pretty appealing too," I said to Kelly, breaking our kiss. She smiled and sighed again.

"I love how you play with it," she said. "I haven't felt that good in a long time, you're really bringing out some feelings I have not had in quite a while." I pulled Kelly's top off, freeing her tits for my pleasure, taking them in my hands as I kissed her, caressing them gently, bringing a soft moan from her as I played.

Kelly by this time had unbuttoned my shirt, and was running her hand through the hair on my chest, reaching down into my shorts, feeling the hair above my cock. "Wow, you have a lot of hair in there!!" she said, playing in my pubes with her fingers.

"Would you like to get a better look??" I asked. Silly question. Kelly undid the button on my shorts, looking me in the eye. She slowly pulled the zipper down about half way, rubbing all over in the thick hair around my straining dick. She then reached in a little deeper, finding my now stiff erection. She stroked it a couple of times inside my pants, then pulled the zipper all the way down so it stuck up into view. She again stroked down on my, holding my erect cock in her hand.

"Wow, that feels good, so thick. I wondered what you were hiding in there all these years."

"You've been checking me out??" I said in mock disbelief.

Kelly laughed. "Of course. I told you I was boy crazy in high school. You didn't think that changed, did you?? I noticed you first from behind-you look really good in jeans-then from the front. A couple of times when we hugged, I thought I felt you against me, so I checked when you pulled away. I liked how you looked, and how you felt. Now I'll get to feel you a lot closer." Kelly smiled and kissed me. I reached over and unbuttoned her shorts, pulling her zipper down as we kissed.

"Now I get to see what you've been hiding," I said, teasing her. I lifted her ass off the sofa, sliding her shorts down, revealing a pair of red lace panties. They were sheer, and I could see they were hiding a nice bush, a few stray hairs coming out from the leg band. "Very pretty," I said. "I was afraid I'd find granny panties."

Kelly looked at me. "A girl has to have a little fun. Nothing wrong with feeling frilly." She smiled and kissed me. I kissed back, enjoying the feel of her lips on mine. I pulled her toward me, rolling her slightly on her side. As she turned in my direction, I pulled down the far side of her panties, working them over her ample but shapely ass. She lifted the hip nearest me, and I slid them farther down, finally working them to mid thigh. I eased them over her knees and to the floor. Kelly, suddenly realizing she was naked in front of me, put her hands across her belly.

"Don't look, I'm so fat," she said, her voice a mix of annoyance and embarrassment. I looked into her blue eyes, and took her hands in mine. She seemed reluctant to let me pull them away from her. I beheld her in all her glory.

"Kelly, love, please understand a couple of things. First, when guy gets a girl naked, it's like he's won the lottery. However you see yourself, we see you as beautiful. We've known each other almost ten years. It's not like I didn't have some idea of your shape-and I'm not exactly fit and trim myself. You don't have to be rail thin to be attractive."

Kelly smiled at me, then kissed me. "You're sweet. But I really need to lose this belly."

"Maybe," I said. "But I still think you're gorgeous, and I wouldn't change a thing." I held her cheek in the palm of my hand. "I've come to love you over the years. I'm not going to let a little belly get in the way." I kissed Kelly deeply.

When we parted, Kelly reached down to pull my shorts off. "I think we need to get these out of the way." The shorts hit the floor, leaving us both naked. "See, I'm not exactly George Clooney," I said, making Kelly laugh. I kissed her again, first on the lips, then down her neck toward her tits. Going for the right one first, I kissed it all around and on the underside, at the same time playing with the left breast with my right hand. Kelly let out a sigh as I made contact with the nipple of her right breast, then squirmed as I squeezed the nipple of her left. Her hands were cradling my head as I attended to her tits, sucking alternately on each, making her nipples stand up. I found she enjoyed having my mouth on her, and I sucked gently, then more forcefully, flicking each nipple between my tongue and teeth. I felt her moan, then sigh as her hips bucked. I released the left nipple and kissed up to her face again. She met me forcefully in a deep, sensuous kiss, full of desire.

Kelly looked at me as our lips parted. "Who needs George Clooney," she said softly. I kissed her again, short and sweet, then worked back down her body, this time passing her boobs and going to her belly. I kissed it all around, telling her I loved every part of her, even the parts she wasn't too keen on. She smiled. "That's one of us." I continued downward, reaching the patch of dark red hair that spread from hip to hip.

'Ooh, a red haired girl," I said "Fiery, I bet."

"I was a lot redder in my younger days," she said, then got a sad look. "Then I went gray. That's why the dark hair now. It's out of a bottle, I'm afraid. Walter likes this color."

"I do too. But I'd love you just as much if you were gray."

Kelly looked down at me. "You're sweet."

I kissed along the top of her bush, ticking the lower part of her belly, making her laugh. I worked across to her left thigh, then back over to her right, then down along the right edge of her pubes. I could see her pussy was already spreading, her outer lips opening to reveal her inner self. I then licked along the edge of her outer lips on the right, just grazing her clit as I reached the top of her slit. She jumped and grabbed my hair, holding my head tight as I licked down the other side, then inserted my tongue just inside her, licking all the way up to her clit.

"Mmmmmm, that feels so good," Kelly sighed as I slowly ran my tongue up and down her slit. She was opening up wide now, and getting quite wet. "I have missed this. It's been so long." Hmm...maybe Walter wasn't so inclined to go down on his wife. I was more than willing to take up the slack. I put a finger in Kelly's pussy as I gently sucked on her clit. She sighed again, and I felt her pussy juice as I played with it. I inserted a second finger and continued to lick. Her hips started to shake as I pushed in and out, finally burying my nose in her bush as I licked inside her. The next thing I knew, she was crying out as she came, her hips thrusting into my face, soaking me with her orgasm. I lapped it up as fast as I could, then kissed her thighs as she held my head close to her. Just then, the oven timer went off. Perfect timing. I hoped it didn't break the momentum.

"Mmmmmm, that feels so good," Kelly sighed as I slowly ran my tongue up and down her slit. She was opening up wide now, and getting quite wet. "I have missed this. It's been so long." Hmm...maybe Walter wasn't so inclined to go down on his wife. I was more than willing to take up the slack. I put a finger in Kelly's pussy as I gently sucked on her clit. She sighed again, and I felt her pussy juice as I played with it. I inserted a second finger and continued to lick. Her hips started to shake as I pushed in and out, finally burying my nose in her bush as I licked inside her. The next thing I knew, she was crying out as she came, her hips thrusting into my face, soaking me with her orgasm. I lapped it up as fast as I could, then kissed her thighs as she held my head close to her. Just then, the oven timer went off. Perfect timing. I hoped it didn't break the momentum.

I looked up at Kelly. "Brownies are done," I said, kissing my way up to her mouth.

"Better go get them, or I won't be the only thing overcooked," said Kelly, kissing me. I got up and pulled them out, setting them on the stove to cool. I returned to the living room to find Kelly sitting up. I sat next to her and kissed her softly. "That was wonderful," said Kelly, smiling. "Better than in my nicest daydreams."

"I'm glad," I said. "I've thought about doing that with you for a long time. It was way better than I ever imagined." Kelly kissed me then held me close. We broke our kiss, Kelly still stroking me. "That feels good, I love your touch," I said as Kelly worked up and down on my reviving cock.

"I love the way you feel in my hand, the way you're swelling." I was. My cockhead was getting bigger as she continued to play with the shaft. She changed her approach so she was playing with my balls as well as my cock. I was getting close to coming. I put my hand on hers, stopping her motion.

"I'm getting close. If you're not careful, you'll be playing in a lot of sticky goo in my chest hair very shortly."

Kelly kissed me quickly. "Mmm, I can feel you pulsing in my hand." She kissed me again. "I bet you have a lot for me." She resumed her stroking, very slowly and gently, up to the head, then back to my balls, then she'd stop for a minute of two, just holding my balls and the base of my cock, edging me, watching the head pulse. "That's so hot, watching you throb in my hand, feeling it at the same time." Kelly looked at me. We both felt my cock stiffen and pulse more intensely. She looked down at my cock as I felt a familiar surge.

"Don't move," I told her urgently. My cock started to ooze come like a volcano spilling over, a thick glob emerging from the head followed by a thick stream of semen that slid down the head, over her thumb, finally dripping into the thick hair above my cock. Kelly looked at my pulsing dick erupting its sticky load with an expression of pure lust.

"Oh, God, Tom, I want that inside me." As she released me, she climbed up to sit on my lap, her red haired pussy now just inches from my pulsing erection. She stroked me slowly, smearing the semen she just elicited from it all over and up and down, and looked at my still seeping cock, contemplating what she was about to do with it. She looked at me and smiled. It was a sad smile.

"It's been 54 years since I had someone else inside me."

"You can still back out of this if you want," I said, wanting to give her a way out if she was still not sure of herself. Kelly looked at me, and kissed me again. She smiled, this time with love and desire in her eyes.