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Mom’s Best Friend

Category: Mature
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“You are joking. Please tell me you’re joking?” I doubted my mother understood the desperation in my voice, but I was disgusted and disappointed. How could she do this?

“I’m not joking Chris.” My Mom was still calm, oblivious to reality as usual. “I told Megan to call you. She’ll be in town next week and I thought it would be wonderful if you could take her to dinner. It’s not like you have this busy social life and you can’t fit her in. You’re always telling me that you don’t get out enough.”

She was right, but the reason I never got out was because I was always working, not because I didn’t have any friends. Being a first-year attorney was like that — 60 hours a-week, at least. And taking an old lady out to dinner? That didn’t count as “getting out”. Not to me anyway.

Megan Davis was my mother’s best friend, had been for as long as I’d known her, and though it had been years since I’d seen her, I couldn’t imagine a worse fate than spending the evening with someone on my mother’s wavelength. My spare time was precious and I had work to do.

“Look,” mom continued, “I know you don’t have a lot of cash to spare. Take Megan somewhere nice. I’ll pay. Just make her feel at home. Please?”

“It’s not the money mom, “I objected, “I just have a ton of work to do next week. I…”

“I gave her your number. I expect she’ll call you early next week.”


Megan called Monday. She was in town for just a couple of days, at a horticultural convention I’d never heard of. I shook my head as she spoke enthusiastically about getting together, thinking, “This is not real.”

I thought about telling her I just couldn’t get away, but she was so enthusiastic about meeting I lost heart for that tactic. We agreed on meeting Wednesday evening, at a high-end steakhouse a few blocks from my office. I hit the button on my cell phone and shook my head again, still not quite believing that this was happening.

My memories of Megan were fairly dim. She had been around a lot when I was growing up, but had moved away about 10 years earlier, when her husband died unexpectedly and she wanted to be closer to her sister. My mother and Megan had kept up their friendship by calling each other, seemingly every day, and my mother visiting her at least once a year. Megan had always been kind and friendly to me, but ten years was almost half my age and she couldn’t possibly relate to my life now.

Predictably, I got to Callan’s steakhouse, where I’d booked a table, almost twenty minutes late. I did have a lot of work on, but it was entirely possible that subconsciously I was trying to make this evening as short as possible. Megan was waiting at the bar when I got there, nonplussed by my lateness.

“Chris, my dear boy.” She opened her arms effusively to hug me. “I’d say you haven’t changed, but that would be a complete lie. What a handsome young man you’ve turned out to be.”

Her dialogue might have been straight from a bad movie, but her appearance almost shocked me. I recognized her easily from memories and pictures, but she looked younger in person than I’d expected, by at least fifteen years.

I’d expected Megan to portray my mother’s age and to a certain extent, her image, but I was dead wrong. I’d forgotten that Megan was 8 years younger than my mother and at 42, she was in great shape, trim, tight and full of life. Megan wore a yellow, red and orange summer dress, a one-piece with a flowery pattern. She had on white casual shoes and big white earrings. Other than that, all she had was a white purse. Her face was tanned but smooth. Wrinkles at the edges of her eyes gave away that she wasn’t thirty any longer, but not much else about her body did. As I cast an eye over Megan’s dress I noticed her trim waist, full hips and beautifully formed breasts. As we were lead to our table I followed her and noticed her wonderfully rounded bottom. This was my mom’s best friend? I shook those thoughts from my head and sat down.

“So,” she immediately reached across the table and grabbed my right hand in both of hers, “tell me all about your first job.”

Over appetizers I told her about my first few months in the law firm I’d been taken on by. She seemed genuinely interested and my mother had obviously been providing at least some details of my life over the last ten years, especially that my social life had all but disappeared lately.

Megan’s hair was jet black, shoulder length and wavy, and her eyes a kind of sea blue. Her face was full of expression as we talked and when her eyes opened wide the contrast against her hair was startling, but I liked that she was engaged in the conversation. This was far better than the lost evening I’d figured was coming my way.

“So, no girlfriend then?” Somehow I knew that one was coming. What is it about that question that all friends and family ask, and everyone who gets asked hates?

“No.” I brushed it off. “Not right now.”

“But you are seeing girls, aren’t you.” Her face was earnest and almost concerned. “You young boys need some of that… companionship. Am I right?”

I nodded, embarrassed, not sure what else I could do. It wasn’t like I was going to admit not having had a good fuck for almost six months!

Fortunately she changed the subject quickly and we got onto the more comfortable territory of my mother’s obsession with daytime TV shows. We ordered steaks and shared sides and the evening fell into a more comfortable rhythm than I had expected, by a long way.

Megan talked about current movies, books and music in a way I hadn’t expected. All because I’d figured she was my mom’s friend and only had similar interests. As each minute went on I realized that preconception was fading fast. I also realized that I’d better quit drinking the wine before Megan caught me looking at her cleavage.

“So tell me,” Megan looked at me intently, “are you seeing anyone right now? You can tell me, I won’t inform your mother if you’re keeping it from her. You’re far too handsome to not have a girl in your bed.”

I wondered if she was a little tipsy herself, but couldn’t believe that two glasses was enough for that. I also noticed that I wasn’t nearly as uncomfortable with the question as I’d been earlier.

“Nope,” I shrugged, “nothing to hide. No one in my bed.”

“Well, we’ll have to do something about that.”

Okay, so I found it a strange comment. Sure, I was thinking she was using a general, royal “we” and her words were spoken in a very offhand manner, but I did puzzle over just how she was going to do anything about it.

We were too full for dessert so Megan finished the last of the wine and we had some coffee to round off our, now chatty, evening. I paid the bill, briefly wondered if it would breach my credit card limit, and tried not to let the shock show on my face.

Having entered the evening wanting it to be a short as possible, I was now wondering if I should offer to extend our chat with a visit to a piano bar I knew that was not far away. I decided that was a good idea but Megan replied, “Oh no Chris, there’s no need for that. You have a car though, right? How about you take me to my hotel? Save me trying to find a cab.”

Of course, I readily agreed.

“That’s settled then.” Megan flashed a smile at me and reached for her purse. “Come on young man.” She reached across the table and took my hand. We got up together and walked out of Callan’s arm in arm.

Megan’s hotel was several minutes away, almost on the other side of town and as we drove she asked many questions about the city. Often my answers were greeted with friendly pats of her hand on my thigh. By now her gestures weren’t unexpected, but I was aware of the effect they were having on me a lot more.

When we got to the hotel Megan directed me to the underground parking lot, rather than the front entrance, and gave me her electronic room key to open the barrier. I guessed that I was supposed to park and escort het at least to the lobby, so found a spot near the elevator, parked, walked around and opened the door for her. Megan offered me her hand as she got out, thanked me and we again fell into an arm in arm walk to the elevator. Once inside, Megan pressed the “6” button for her floor. A few thoughts crossed my mind but I shook them away quickly… that was just plain crazy.

Megan continued our conversation, almost completely one-sided at this point, while I followed quietly and my thoughts filled with what we may or may not be doing. Her matter-of-fact tone and actions lent innocence to our actions, but there was no doubting the fact that I was accompanying a beautiful mature woman to her hotel room — not something a 22 year-old can ignore, or take for granted.

When Megan opened her room door an entered she didn’t indicate for me to follow her, but I did so just the same. No matter what this was about, I knew that I was supposed to follow. Once inside she placed her purse on one of the two soft chairs beside a small table. The Hotel room was standard, upscale for sure, but not luxury. The bed was pristine with lots of pillows of different sizes. There was a small suitcase on a stand and a few small artifacts Megan had left around.

Unsure where to sit, I stood and watched as Megan bent down to a small refrigerator and pulled out a bottle of wine. She found a couple of glass tumblers and held one of them up, along with the wine. “This okay?” I nodded and she indicated I should sit. I sat on the edge of the bed.

Megan turned and gave me one of the glasses she’d poured and then she sat on the other chair next to the table. Before taking a drink of her wine she unclipped her large white earrings and put them down. Picking up her glass again, she leaned over to me with it and offered, “Cheers.”

Our glasses clinked and I took a full mouthful of the wine. Then I reached over and placed my glass on the table also, conscious that if I kept it in my hand I would drink it quickly and I still had to drive home.

“You look a little tense.” Megan held her glass and sipped again. “You’re not nervous are you?”

I tried to look relaxed and shrugged. I should have asked her, “Nervous of what?” but the truth was, I was nervous!

“Relax.” Megan urged, putting down her glass and moving to sit next to me on the bed. “Nothing to be nervous about. I don’t bite.” She placed her hand on my thigh and let her shoulder rest against mine. “I’ll only bite if you want me to.” Megan gave a little laugh. “I much prefer the softer side of things though, don’t you?”

I turned my head slightly and Megan brought her lips to mine. There was no urgency as she kissed me, just a gently kiss that allowed me to feel her soft lips and start to kiss her back. Our mouths opened together and I felt her tongue softly enter my mouth. There was still no urgency in Megan’s sensual movements, but I did feel her hand rub my thigh a little harder as her tongue found mine and we explored each other’s mouths.

When we broke the kiss Megan inclined back on the bed a little, leaned on her arm and looked up at me. “That wasn’t so bad, was it? Feeling a little less tense now?”

I smiled down at her and leaned over, my turn to kiss her. Megan eased back further as we kissed, lying on the bed now. Her hand came up to caress my neck as I played with her tongue and felt her soft lips, urging me to stay with her and enjoy the long kiss. There was no doubt I was less tense, and now aroused, but it was still slightly weird, the thought of making out with my mom’s best friend. Megan’s hands came to my sides, feeling my flesh through my shirt, making me feel better by the moment.

“Sit up.” Megan instructed when we broke the kiss, pushing herself upright and swinging her legs off the bed. Two steps and she was in front of me. She looked down and just had time for a quick, wicked smile, before kneeling in front of me.

“You don’t mind if I have a look in here, do you?” Her hand massaged the front of my pants and she looked into my eyes. “No, doesn’t feel like you mind.” She started to pull away my belt and her fingers worked on the clasp and zipper of my pants.

I eased my weight off the bed when she grabbed my pants at the sides of the waistband and pulled. Megan pulled my pants underwear away with one swift move and then pulled my shoes and socks off so she could complete the extraction of clothing from below my waist. I was hard, already throbbing, already red, when her eyes came back to see what she’d uncovered. I leaned back a little, letting my shirt pull away from my erection. Megan took in the sight for a moment before she reached out to take hold of me.

The luscious feeling of a new hand around my cock was sublime. I looked down and watched her hand as it varied pressure on my shaft and explored me.

“Not such a small boy anymore, that’s for sure.” She smirked, watching her hand now as it pulled my foreskin away from the head of my cock and down the shaft. “Been a while since I’ve seen an uncut cock. Beautiful.” She licked her lips.

Megan’s hand felt warm and soft as she gave me a few long, delicious strokes. I groaned with pleasure as she worked my cock, a groan that brought a wide smile to her face. She looked up and watched my face as she stroked me again. “Does that feel a little better?”

I nodded, feeling incapable of adding anything worthwhile to the conversation at that point. Megan slowly brought her head closer to my cock. I knew she was going to take me in her mouth, but the deliberate way she moved was all the more erotic because she appeared to be savoring the move. I watched as my cock disappeared under her head and then I felt the warm wetness of her mouth close over me.

Megan didn’t immediately start working me up and down, but kind of stayed there for a few moments, swirling her tongue around the head of my cock and sucking on me. Again, it seemed like she was savoring the moment, showing more experience and restraint than I was used to in the girls I’d known.

As she started bobbing her head up and down on me she brought her hands between my legs and eased them apart. This allowed her to make longer strokes on me, taking me to the back of her mouth and allowing her tongue to brush along my cock with each stroke. Megan worked her hands further up my thighs and her fingers reached my balls. As she gently eased them out and up I felt a huge burst of excitement and groaned loudly.

Leaving one hand to play with my balls, Megan brought her other hand to wrap around my cock and stroke and twist in time with her bobbing head. She took a moment to crane her neck and look up at me. Obviously seeing the pleasure in my face, she smiled as much as was possible with my cock in her mouth, and resumed her work.

Megan had only been stroking me for a few minutes when I realized that I was approaching climax. I worried momentarily about cumming too soon, spewing cum into Megan’s mouth and appearing to be a little boy who couldn’t control himself. Then I realized that Megan knew exactly what she was doing and probably knew exactly where I was on the excitement meter. I relaxed and let her continue, resigned to her having control over my approaching orgasm.

Lifting her mouth off me, but continuing slow movements with her hand, Megan looked up at me and said, “It’s okay baby. Let it happen… relax and let it be good.” Then she clamped her mouth over me again.

By then it was impossible to do anything but comply with her soft words. I felt her mouth slip up and down my shaft, her tongue licking at the head of my cock as she almost came off me, then descending on me again. Her hands moved in complete synchronicity, one holding my balls, making sure the varied the pressure and increased the pleasure and the other slipping up and down, supporting her mouth as she slowly eased me closer to exploding.

By the time my climax arrived Megan had her movements down to slow and essential. It was like she knew exactly how much pressure to exert to keep my climax at bay but building. When it started she stroked faster and clamped her mouth tighter around my cock.

My whole body shuddered as the climax broke, sparking through my every nerve with red hot pleasure and divine release. My cock started twitching in Megan’s mouth and had pulsed inside her several times before the first spurt of cum shot out from the end of my cock and into her mouth. Megan didn’t flinch as she stayed covering me and I twitched several shots into her. As my cock started to relax a little and the flow stopped Megan sucked hard on me, her tongue swirling as she tried to collect all of my juice.

When she pulled off me finally, I slumped back on the bed and sighed deeply — reveling in one of the biggest climaxes of my life.

Megan kept her hand on my cock as she came up from her kneeling position and sat on the bed. “That was nice,” she cooed, “I take it you enjoyed as much as I did?” I could hear the laugh in her voice but felt her eyes looking down at her hand and my cock.

“That was… spectacular.” I managed to reply after a few seconds.

“Good.” Sue leaned back and looked at my flushed face. “You have a lovely cock here. No pressure, but I’m looking forward to feeling it inside me.”

By now I felt no pressure at all. Megan was no longer my mom’s best friend, but was now a seriously hot older woman and I now intended to make the very best of our time together.

“Would you like to take my dress off for me?” She asked, standing up in anticipation of my answer.

I got up from my prone position and moved to stand behind her. My cock bounced in front of me, proud of its release, still swollen but no longer erect. I reached up to the back of Megan’s dress and started to pull on the zipper. I eased it down to her bottom, revealing a white bra strap on the way down and the elastic waistline of some white panties. Megan shimmied her hips as the dress fell away, easing it over her hips to fall in a heap around her feet.

“That’s better.” She turned to face me.

Megan’s body was in great shape. Sure it wasn’t as tight as a twenty year-old’s would be, but she was in great shape for her age, a shape that was hot as hell now that I’d got over who she was. I ran my hands over her midriff, feeling her skin. I looked at her chest and then down to the white panties that covered her pussy. I wanted to see all of her.

I reached up to unclip her bra but Megan was a tiny bit ahead of me and reached behind her back to help. The fastener straps fell away to her sides and her cleavage slipped a little. I completed the job by taking the cups of the bra in my hand and easing it away to reveal her breasts. Without the support of the bra Megan’s breasts sagged a little, but they were big and had large dark nipples that still pointed straight out. I took a breast in each hand and felt them, pushing those hard nipples back as I delighted in the weight and softness of her breasts.

I let go of one breast, held the nipple of the other up and brought my mouth to suck on it. I felt Megan’s hand hold my head into her as I sucked and played with her nipple in my mouth. I continued to use a hand to feed her nipple to my mouth and let my other reach around to feel the skin on her back. I made several exploratory moves down her back to the elastic of her panties, the last one letting my fingers slip inside and grasp her buttock.

When I pulled my hand out of the rear of her panties I brought it around to the front, slowly descending down between her legs. I felt Megan’s legs open slightly, allowing me to feel the heat from her pussy as I followed the crease of her pussy lips down between her thighs. I pressed my fingers hard into her as I traced the crease up and down a few times. Megan moaned when I pressed onto her clit, let my hand come up and then slip quickly inside her panties.

Inside the material of her panties she was hotter than ever, and wet. My fingers were instantly coated in her juices as I explored her folds. My middle finger was inside her quickly and easily and it felt like she was so wet she would almost drip off my hand. I pushed deep inside her, my mouth now coming off her nipple. Megan looked at my face and sort of sighed and smiled at the same time. “I want something else in there.” She reached out and found my hardening cock. “Feels like you’re ready. Gotta love that about a younger man.”

Megan stepped back, my hand came out of her panties and allowed her to pull them down and step out of them. She moved back to the bed and pulled me with her, by the cock. When she was fully lying out I looked down and saw her pussy for the first time. It was neatly trimmed above her opening, but shaved around her lips. All around she glistened with her juices, spread by my hand. I started to lean over, intent on tasting her.

Megan caught me before I got my tongue between her legs. “I want your cock baby. Now.”

I changed position and kneeled between her open legs. My cock was now fully recharged and standing to full attention as I looked down at Megan. She raised her arms, inviting me on top of her.

I slowly descended and Megan reached out to take my cock in her hand as I got into position. She lost no time in positioning me at her opening. All that was left for me to do was thrust into her. I did so with a positive move, one long swift push that her pussy accepted with a warm, slick covering.

I paused when I got as deep as I could go. Megan was smiling, enjoying me inside her. “You like?” She asked.

I nodded, watching her face intently as I pulled slowly out of her. Megan’s eyes closed as I moved, savoring my cock moving inside her. “I like.” I answered.

As I started to thrust in and out of her, Megan shuffled, opening her legs and bringing her kneed up a little to allow me the best access she could to her sweet pussy. Her hands clasped my ass cheeks and urged me to plunge as deep as I could inside her.

“You feel so good.” She panted as I built up a rhythm. “I love to feel a young guy fucking me. You ever think about fucking an older woman?”

“Not until this evening.” I admitted. “You feel amazing.”

“Here,” Megan shuffled a little, moved away and my cock slipped out of her, “try this.” She had moved to her side, hitched on leg up and invited me to straddle her straight leg and push my cock back into her pussy.

Again, that first thrust into her was divine. I looked down and saw Megan shuffled a little more so I could move more easily. I reached down and started to finger her clit and the top of her pussy, feeling the side of my shaft as it plunged into her and slowly withdrew until almost out. Each time I let the rim of my cock come out of her pussy and then push the whole cock back inside, sliding that length with deliberate and long strokes.

“Yes, there.” Megan whispered as I fingered her. “Oh yes.”

I watched her face and kept my strokes long and solid. I saw her arch her head back on the bed as she got close to climax. Megan seemed breathless now, almost unable to move as my fingers stroked her slit and my cock trust into her. I looked down and watched my cock disappear, saw my fingers playing with her and then looked up again at Megan, lost in pleasure now.

I saw her face freeze and sensed that she was cumming. She moaned and I knew that I was doing the right things for her. “Yes.” She breathed as I slowed my fingers to simply apply pressure in time with my thrusts. “Oh God, yes.” Megan almost sighed as she came.

Her whole body shuddered, almost forcing my cock out of her pussy as she cramped up. I managed to keep it in there though, continuing to move in and out while she was flooded with climax. Megan urged me on through her climax by trying to push back with each stroke I made. Then she shivered a little, opened her eyes and look at me. She nodded, letting me know it was good.

“Keep going baby,” was the first thing she said. “Keep going, cum for me. I want to feel you cum inside me.”

The combination of her words, watching her cum and seeing my cock slip in and out of her was all it took. I was almost surprised at how close I was to cumming, so soon after the first, and right up to the final few strokes I pounded into Megan.

I watched her face as I came. Her eyes locked with mine intensely as I made one final stroke and the orgasm burst inside of me. I grunted and tried to keep thrusting as the climax broke, my body hindered by the pleasure taking up all the bandwidth of my nervous system and flooding me with pleasure. Megan’s eyes widened when the first shot of cum hit her pussy, then her face softened to a smile knowing it was powerful and good for me.

I slumped to lie on the bed and Megan softly moved next to me, reaching over to let her hand gently cover my deflated cock. We looked up at the ceiling and caught our breath.

“You have a lovely cock. You know that?”

“Your body… fantastic.”

“Thank you.” Megan squeezed my cock, her fingertips making sure she touched my balls.

“You better not tell my mother about this.” I laughed, the weight of the last few minutes catching up with me.

Megan joined my laughter. “No fear of that. She’d never talk to me again. It’s been a memorable night though. I hope you don’t regret meeting me.”

I shifted up onto one elbow and looked at the flushed face of my new lover. “No,” I said quietly, “It’s been a wonderful evening.”

“Good.” Megan sighed and closed her eyes in content. “You think you’d like to stay for breakfast? The hotel has an excellent buffet.”

I kissed Megan. “That would be nice.”

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