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Mom’s “Conservative” Friend

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Double Penetration

Unexpected things can crush you, but good, unexpected things happen, too. Last year one of those good things happened, and I want to share that experience. I may die in an auto crash next week, but I’ll go out a little happier if I put this down in writing for other people to enjoy. It’s only right, because I have enjoyed others’ stories.

Some background, first. I’m 26 and live with my mom, a fantastic woman who’s my best friend and biggest fan. I’m teaching, saving for a condo or maybe even a house one day, but really like the arrangement I have now. Mom has company, I have company, I help with money towards expenses, and I try to help out in any way I can to do my fair share of chores. Mom has zero interest in another guy since my dad walked out years ago, even though I keep encouraging her. That’s a mystery to me, but after years of encouragement to date, I have come to accept that she can do anything she wants-and will.

So my mom has a friend from way back I will call Diane. She visits every once in a while for a few days, usually a long weekend. Diane is okay, cordial and pleasant enough, but she and my mom seem to have a great friendship and things in common that I know nothing about. She seems a little…cool to me, kind of businesslike, not the warm bubbly type I like. But she’s my mother’s friend, so no problem at all.

Mom and Diane planned a weekend visit in October, and I mean really planned. They knew the museum, restaurants, shopping places they wanted to go and when they would go there. The only catch was that mom is a nurse, with extra training and experience with burn victims, so she can get called in to work almost any time in an emergency. It doesn’t happen often, so no big deal.

The weekend arrived, and Friday night the two of them got a Lyft to their favorite Mexican restaurant. They loved the carnitas and the margarita pitcher special, but were smart enough to know they shouldn’t be driving after consuming even half a pitcher. I had a vague plan to see if some friends were going to our usual bar after the music started, but got caught up in a west coast playoff game that was really close.

Mom called my cell around 9 and told me she was coming home asap. Some “Happy Hour Harry” as she called them, had been in a bad crash. She had already called a Lyft and was coming home to change.

“Make some coffee for me, Dear. I’ll be home in 15 or 20 minutes and need a little boost.”

I made the coffee, running in and out of the room to keep an eye on the game. Mom and Diane arrived in a burst of laughter, and mom grabbed some coffee before racing off to put on her scrubs.Two minutes later she was dressed and making apologies to Diane as she ran out the door. She carried a bottle of mouthwash in her hand. Coffee was good, but my mother would never risk coffee breath while working shoulder to shoulder with someone.

“Take care of Diane, honey”, she called out as she left.

Diane laughed, and when she did, I realized that she was slightly inebriated.

“Pitcher margaritas?” I asked, using my mom’s phrase.

“Soooo good. I drank two, but your mom always goes slow. She didn’t even finish one. In the back of her mind she knows she can always get called in to work, so she never drinks too much. It’s almost as if she knew she was going to get called in.”

“Well, it is Friday night. She always says weekend nights are worst. This being a small place, there aren’t that many nurses with her expertise.”

Diane nodded, grabbed the edge of my chair for support to steady herself and asked about the game. I was surprised she had any interest, and figured she was just making small talk.

“My dad played semi-pro ball once.”

My jaw dropped and I made a face of surprise.

“Back in 1962. Maybe 1963. I think it was for some minor league teams that had a connection with the Washington Senators.”

We continued to chit-chat about that for a bit in between game action. Diane sat on the arm of the big stuffed chair I always sit in to watch TV. Maybe she wanted company, maybe it was our new camaraderie. Who knows? When a commercial came on I reached out and half patted, half rubbed her back briefly, saying something like “I had no idea”.

“Oooo, that feels good. Yep. I think Dad was good, but not great, so things never happened like he hoped. But he did real well in Real Estate, and he always seemed happy, so you just never know…”

Diane’s voice trailed off as I continued to rub the small of her back. In truth, it felt a little odd to be rubbing the back of this woman who was familiar and friend, yet kind of a stranger to me.

“Mmmm, that’s nice.”

“Really?” I asked. “I’m hardly doing anything, just making little circles with my hand.”

“I don’t know if it’s me or the margaritas, but it just feels good.”

“Stretch out across here and I’ll rub your back. You won’t be able to see the game that well, though.”

Under normal circumstances, that was a crazy idea, but alcohol changes everything. Diane made a noise of happy surprise and slumped across the chair and my lap, then scooted her body around a bit to make herself more comfortable.

“Game, Ankara bayan escort shlame”, she said. “I’ll take a back rub any day.

“I’m no expert” I said. “I just rub mom’s shoulders and neck sometimes when she’s tired, but I never did her back.”

“You can do my neck and shoulders next”, Diane said laughingly.

“Sure”, I replied. I couldn’t think of anything to say. Or maybe a hundred things went through my head and I couldn’t decide the right reply. This was such a different situation than anything I was used to with Diane.

I started to continue my massage of Diane’s back through her purplish blouse, but it was coming out of her skirt so I pulled it out the rest of the way and started rubbing her back with my bare hand. It wasn’t anything sexy at all, just an open hand making little circles on her back, but Diane said something approvingly. I couldn’t understand the words, but just the tone alone said she was happy.

I continued the circles for a few minutes, just varying the size of the circles, the location and pressure. Total amateur stuff. A couple times I crossed the bra strap with my hands, but Diane said nothing. Touching a strange woman’s bra strap seemed a little bit erotic, and so were the sounds Diane made. I started to get hard, and was frankly a little bit embarassed about it. Maybe if I was a sophisticated forty-year-old who had been with lots of women, it wouldn’t be sexy at all and I wouldn’t be hard. But I wasn’t. I didn’t have the nerve to undo her bra strap, so I just slipped my fingers underneath the strap and massaged lightly with my fingers. After doing this several times I accidentally undid one of the hooks. I was about to re-snap it when Diane said “Undo the other one. I hate bra straps when I’m hot.”

So I did. Gladly. Gleefully, and swept my hands up and down the whole expanse of Diane’s back. Her skin was soft, and touching it seemed very human. Would we ever have the same relationship again?

After another few minutes of doing the same thing I was uncertain what to do next, so I used my finger nails to scratch really lightly.

“Ohh, that’s nice…Ooooo…ooo-ooo-ooo…I love it. You have magic hands.”

I laughed. I had no idea what I was doing, but I did like making this woman feel good. And I got to feeling a little bolder, so gradually I started to let my right hand go a little lower each time, letting the fingers slip under the waistband of Diane’s black skirt. I couldn’t feel much, so I switched to rubbing a little lower outside the skirt. Not rubbing the meaty part of her butt, but the top where the back transitions to the butt. I applied a fair amount of pressure, trying to disguise what I was doing as just normal massage. Diane didn’t stop me. On the contrary, her contented murmurs told me she was enjoying what I was doing. I really wanted to caress her round butt, but lacked the nerve for a direct attack. It seemed crazy anyway. What to do next?

I thought for a bit, then came up with a plan of attack which involved light strokes down the side of her butt and then the tops of her thighs. Nothing outright sexy, just continuing this “innocent” massage. I suggested Diane move forward just a bit and she complied, but then something happened I hadn’t anticipated.

“My bra’s coming off! Help me.”

Indeed it was, and I caught a quick glimpse of the side of one white breast before Diane clutched her blouse and bra. Not sure what to do or say for a second, I had a moment of inspiration.

“Why not just lie down on the couch?” I suggested. “I can just sit on the coffee table.

Diane thought for a moment or two, and I was sure our fun little massage session was about to end. I could sense the wheels turning in her head, but those gears were lubricated by alcohol. The fact that my mom would probably not be returning anytime soon played a part, too.

“Okay” Diane said cheerfully. As she got up, she swayed a little, holding her blouse and bra against her chest. She plopped down on the couch. She faced out for a few seconds, then changed her mind, and turned her head towards the couch. I paused for a second, unsure how to proceed. I really wanted to touch those bare legs. Then a path forward suddenly became clear.

“Mom loves it when I massage her feet. Let me do your feet.”

Diane squealed in delight.

“You really know how to please a woman. Back scratches, foot rubs. You can practice on me any time.”

I began a slow massage of the bottoms of the feet, stretched the toes a little, caressed them individually and did absolutely anything I could think of. Then I repeated everything, and slowly moved up to Diane’s calves. There was no reproach. No words of caution. I kept my hands focused on massage, but my eyes moved ahead, up Diane’s body to her thighs and full, womanly butt. I didn’t really expect to score there, but I was sure going to try. Slowly, slowly I worked my way up. Innocently, slowly, just an extra half inch extra on one stroke and another half inch a 30 seconds later.

Before long I was running my left hand up and down the backs of Diane’s soft, but shapely thigh while my right hand Escort bayan Ankara caressed behind her knee and kept squeezing her calf. And there was no protest! Diane kept up her string of contented murmurs, o-o-o-o sounds and little feminine sighs of content.

After repeating myself once too often, I made a bold move and shifted position to put one knee between Diane’s legs and massaged a thigh with each hand.

“Ummmmm…that feels good. This is kinda sexy, isn’t it?”

“Yeah. It is. YOU’RE sexy. I had no idea. I never thought of you like that. “

Diane laughed at that. And laughed. And laughed. I was happy she laughed because she might have been irritated instead.

“Y’all don’t know me that well, _________. Your mom knows the real me. Not many guys. I’m glad you think I’m sexy, though. Most people think I’m a buttoned up control freak.”

I didn’t know what to say, so I said nothing. I let my hands do the talking. I had progressed upwards and was now massaging under the black skirt and my hands were mere inches away from whatever panties Diane was wearing and the feminine charms they hid.

“Oh, God…Oh, God. I’m starting to get really turned on and I haven’t a clue what to do about it.”

“Do nothing”, I said. Just enjoy.

“That’s so easy…and so hard. So hard. I don’t know why letting go is so hard.”

Again I said nothing. I just didn’t know what to say.

“Just be gentle” Diane murmured. “I know you will, though. You have gentle hands.”

My mind whirled. Did I just hear right? “Just be gentle” was not how you told someone to stop. In fact, it was the opposite. I had been given “green over green” in train lingo I once heard. A clear track. Wow!

I continued my massage of Diane’s lovely full thighs for another minute, then flipped up her skirt a few inches so that my hands were unobstructed. The sight made me breathless. I took a deep breath and marveled at the pale cheeks escaping from the side of black high-cut panties. My hands kneaded her soft thigh flesh for a minute then I ran them slowly up the sides of her delightful ass and down. Up and down. Up and down, Slowly moving, on top of her panties, then a little inside the band. Diane squirmed slowly and made noises that sounded like ummmmmmph. Or UMMMMMMMMMMph!

Because she had black panties on and because the light wasn’t great, I couldn’t see the details of her labia and vagina beneath the fabric, but it didn’t matter. With my fingers I caressed the infinitely soft skin where thigh gives way to more intimate charms. I loved the feel of her skin. My fingers danced lightly on silky panties pulled tight over her mound in a test of her desire. I teased her, then pulled back, and teased her again. She didn’t answer, but the way her body was moving was all I needed to know. She was enjoying every moment.

I slid both hands beneath the leg bands of her panties and made some noise myself. I massaged soft ass cheeks discreetly, then retreated and used both hands to push against the fullness of her pantie clad butt on the outside. I pushed and pulled skin, massaging one way, then another, then going back to teasing Diane through her panties, probing for the soft spot where her vagina started, probing for the clitoris…teasing, and teasing some more. But then the time to move forward announced itself in some corner of my brain. I grabbed the waistband of Diane’s panties.

“Lift up” I commanded softly. And she did. I pulled her panties down slowly as she arched her body to let me. I saw two lovely pale ass cheeks briefly as I maneuvered the sexy garment down across thighs legs and finally feet. I heard Diane take a deep breath.

“You’re beautiful” I said. “Just beautiful.”

Diane whispered a thank you, then I gave in to my lust and leaned in to push my face against those sweet pale cheeks. I kissed each one a dozen times before pulling back slightly to better appreciate the glistening lips of Diane’s pussy. I kissed the area around each labia and inhaled the scent of Diane’s wetness, then inhaled again. Women smell wonderful to me. I’m sure it’s a primal thing. It just makes me crazy with lust. I hoped to lick those wet lips and hear Diane cry out in joy when I sucked her clit, but sensed this was not yet that moment. We’d need a change in position for that, and I didn’t want to risk the moment I had and the chance to explore her pussy and tease her clit with my fingers.

I licked my index finger and slowly inserted it between the wet lips of Diane’s warm vagina. She moaned in pleasure, and I moved my finger in every imaginable way; twisting, teasing, probing. I pulled out and found the little nubbin of her clitoris and flicked it gently again and again. Diane gasped in pleasure. She had a largish clit, which made teasing it all the easier (my last girlfriend had a small clit that I sometimes lost in the heat of the moment).

I was in heaven and Diane right besides me. I sucked my thumb for a second to moisten it, then inserted it between the sweet folds before me. I felt Diane’s pussy grab my thumb and I extended my index finger and middle finger to rub that little rubbery bud at the Bayan escort Ankara same time. More moans. Louder. Diane, the woman who seemed so businesslike hours ago was moaning wildly, and making loud sounds of pleasure. I increased the tempo of my sweet torture on Diane’s engorged clit and she soon came in a series of unh…unh…unh sounds that are the best sounds in the whole world. Diane grabbed my hand for a few seconds and stiffly froze her body while the sensations melted away.

“Omigod. Omigod. Omigod that was good. Sooooooooooo good!.

She turned to face me and pulled me close to kiss me.

I laughed.

“What’s so funny?”

“Ummm…it’s just kind of funny. Usually the kissing comes first. And then maybe breasts, the other stuff…”

Diane laughed too, and sat up.

“You’re right. It IS funny. And so unexpected. And you still have all your clothes on!”

Diane looked at me and shook her head.

“I don’t have any explanation. I was just happy to be close to someone nice. And you know what? My breasts would love to meet you”, she said, lifting her blouse over her head and taking off the loose bra. She smiled.

I smiled and reached out for a breast. It wasn’t big, but it had a nice shape and a nice nipple. The biggest treat of all was that she wanted to share it with me. THAT was very sexy. I took a deep breath and kissed around her breast then gave the nipple itself a quick kiss and suck. Diane shivered then looked up at me.

“What now? When is your mom coming home? What do we do? How am I going to look at your mom with a straight face?”

“I don’t know. A call at this hour is never good. I just…I’m pretty sure she’ll be out all night. She’ll come home as soon as she can if it’s an adult, but if a kid is involved, she stays longer-even if she’s not on the clock.”

“I gotta pee. And could I get some cool water? Suddenly, I’m thirsty. And nude. I am NUDE!”

Diane disappeared into the hall bathroom, and I watched her sweet ass cheeks bobble slightly as she went. She was around 50 and still had a really nice ass. I had no idea.

I got the water and met Diane in the hall when she came out of the bathroom.

“I have no clothes on. I don’t even care. Letting a man see me nude is a kind of relief almost. No more facade, no more pretending…”

Diane drank some water, put the glass on the hall table and wrapped her arms around me in a long hug.

“What about you?” she whispered. I am so happy right now, but–“

My phone beeped, interrupting. It was Mom and she confirmed in a text that she would be away all night. “Tell Diane I am so, so sorry”, she continued, then “gotta go”.

Diane read the text with me, then spoke.

“She doesn’t have to be sorry. This was an amazing gift. I was about say I’m so happy right now, but I’d be even happier once I take care of you.”

“Take care of me?” I asked.

“You know”, she smiled coyly. “I want to give to you what you gave me.”

“You don’t have to” I said, giving her an out.

“Yes, I do” she said. “It’s only right. Plus, I want to. I really want to.”

She practically whispered the last sentence and I thought it was one of the sexiest things I’d ever heard. This adult woman wanted to please me. We hugged again, and it was amazing to me how natural and how good Diane felt in my arms.

“Okay. I want to do something, too, though” I said shyly. “I want to taste you. I want to savor your…sexiness in every way. I want to be crazy good for you.”

Diane smiled, and it was like a warm wash over me.

“Promise?” she said with a tilt of her head.

I shook my head in wonder and led this nude woman down the hall to the guest bedroom, stopping to let Diane retrieve her clothing from the living room.

A minute later we were wrapped tightly in each other’s arms on the bed. It is nothing short of amazing to me that two people can get so close, so quickly. I sucked Diane’s nipples and gave her breasts a full ten minutes of attention, then kissed my way down her body, hearing her protests all the while that it was my turn. It was my turn. I was using my turn to do what I wanted, which was to lick the pussy of this woman who was growing on me with every minute.

Diane moaned with almost every kiss, and when I got close to my target, I kneeled on the carpet, spread her legs wide on the bed and proceeded to lick suck, nibble, mouth, tease and do anything else I could think of, to every inch of her vagina. I loved Diane’s wrinkled labia and couldn’t get enough of those sweet lips and the pea sized clit where they came together. I loved her taste. I went crazy on her, pulling her lips with mine, then pulling them again–and again. I chased her clit around with my tongue and soon began a rhythm with my lips on her clit: sucking, releasing; sucking, releasing; sucking, releasing. I increased the speed and it didn’t take long for Diane to come. I felt her body lift and stiffen, then she half screamed in pleasure and grabbed my hair with one hand and grabbed a ball of sheet in the other.I both felt and saw her body clench and release as I continued sucking her clit, then switched gears to put a gentle pressure on the tiny pearl as waves of pleasure slowly subsided within her. I turned Diane over, kissed her ass, kissed the back of her thighs and then moved alongside her body to spoon her while her breathing returned to normal.

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