From Friends to Friends with Benefits [mf][friends][fingering][blowjob][creampie]

I can’t believe what I’m hearing or seeing.

Amanda. The millennial. Mandy. She wants to fuck me? Right here and now?

Obviously I’ve often fantasized about having sex with her, or even just seeing her naked body. She’s 24 and skinny with small tits and a nice smile. What’s not to like or be curious about?

But now here we sit, alone at her place uptown and she’s actually interested in making it happen? To what do I owe this extreme good fortune?

A couple of hours earlier, I was sitting at the restaurant texting with her and our other friend Matt. I was on time, they were late. What else was new?

Amanda was in an Uber a few minutes away and Matt was MIA as usual.

“Prolly gonna no show on us,” I texted her. “He’s the worst!”

Secretly, I had hoped he wouldn’t show up and then it would just be me and her. Two’s company, three’s a crowd, after all.

I’d known Amanda for a few years from work and after she quit to go work somewhere else, we all kept in touch. Mostly it was bitching about our jobs and in the case of Matt and me, our wives.

But my marriage was over now and I was still getting used to not having to worry about what she might think of me being out with a single, attractive, young girl literally half my age.

Amanda walked into the bar, ten minutes late with that smile that said, “I know I’m late but I don’t care.” I smiled back, thinking how hot she was with her mildly tomboyish looks and skinny figure.

“No Matt,” I said. “The fucker bailed…again.”

“Are you serious?” she said, adding “I love the guy but seriously, who fucking does that every single time?”

“Whatever,” I said. “We can hang out. I’ve got all night.”

We grabbed a couple of drinks and split some nachos. Suffice to say, we were both feeling a bit happier after that and much more relaxed.

It was her that suggested we hop in an Lyft and head back to her place. I figured her gay roommate would be there, but she explained that he was out of town, shooting some story for work.

“Huh,” I thought. “Just her and me back to her place?”

This was going somewhere I didn’t expect at the beginning of the evening.

The Lyft ride was short and pretty quiet. We kept grinning at each other and the driver probably thought we were insane. Neither of us really cared at that point.

She gave me a quick tour of the house and we poured a couple of drinks. Me a gin and tonic, her a glass of red wine. They disappeared fairly quickly and more booze followed.

I don’t remember what we talked about, but I’m sure it was the usual stupid stuff like how her brothers were idiots and how she couldn’t wait to get away from her busy job for a bit.

Exactly what happened next was, well, a bit crazy.

“I think we should have sex,” she said. Point blank. Looking me right in the eye.

“Did you just say we should have sex?” I said.

“That’s what I said. We should have sex,” she said again. “You’ve always wanted to fuck me and, to be honest, I’ve been looking for a new friend with benefits since I dumped that last dude.”

“Well that’s nice,” I said. “Mandy needs a fuck, and the old guy is here, so why not? Really makes me feel wanted.”

“Hey. It’s not like that,” she said. “I’ve wanted to fuck you since I first met you. But, you know, there were circumstances,” referring to my previous situation.

“Ok. Sure. I’ll buy that. Take your shirt off then,” I said to her with a wry smile. “I’d love to see how much padding you wear in that bra.”

“Stop it! I have tits!” she said as she reached down with her arms crossed and starting pulling her shirt up, stopping halfway before revealing her naked chest to me for the first time.

“Ready?” she said, as she lifted her shirt up and over her head, revealing a cute little bra covering what little breasts she had.

It was a sports-type bra and she quickly pulled it off over her head next, revealing a pair of small, but extremely sexy tits with bigger puffier nipples than I would have guessed.

“Oh wow,” I said. “I take it all back…those are fucking perfect.”

I took a deep breath and stood up to put my hands on her tits and give her nipples a squeeze before leaning down to suck on one of them while I pinched the other between my finger and thumb.

“Oh my god,” she gasped. “Am I really doing this? With you?”

“Oh, we’re doing this,” I said. “I have the user story already,” referring to our jobs as product managers.

“As a old 44-year-old dude, I want to have sex with a chick half my age so I can feel better about myself,” I said.

She laughed.

“Good story. I think that’s a 6 point task?” she asked.

“I seriously don’t care how many points it is,” I said. “I’m all about cadence right now and we’re losing momentum here!”

Along with the loose t-shirt and bra that were now on the floor, she was also wearing her black yoga pants which I knew from years of friendship that usually meant she was on her period.

“Tell me it’s not that time of the month,” I said.

“No…it’s done a few days ago. I just felt lazy today and couldn’t be bothered to dress up,” she said.

Phew. I mean, I would have fucked her anyways, but I’m not sure whether she would have gone for it. Whatever the case, it didn’t matter. We officially had no barriers to entry, as they say.

I pulled my own t-shirt shirt over my head, and asked her what she thought of my dad bod.

“Decent for a 44-year-old?”, I asked.

“Not bad…better than fat Matty, that’s for sure,” she said.

“Wait. You haven’t seen him naked have you??? OMG…you fucked him too, didn’t you!”

“NO!” she exclaimed. “Never! Ew gross!”

“Ok, ok,” I said. “I’m sorry I mentioned it.”

She pushed her tights down to her ankles and pulled them off her feet revealing a pair of thin Lulu thong underwear and the distinct outline of her pussy lips. I reached down and traced the line of her slit through the fabric with my finger. She was already a little damp down there and I too was rapidly getting hard.

I pushed down my pants and underwear at the same time, revealing my ever-hardening cock to her for the first time.

“Wow! It’s bigger than I imagined?” she said.

“I like it,” I said. “And the admittedly very few women who’ve had experience with it seem to as well.”

Her hand was on my hard-on now which was basically at full mast and the large head of my cut cock was throbbing a bit. She started rubbing up and down the shaft while I pushed my hand down into her panties and found her wet slit. I pushed a fingertip inside and made her gasp.

“I need to see your pussy,” I said. “And I need to taste you.”

“You like going down on women?” she asked.

“I love it,” I said as I pushed her panties down and dropped to my knees to get a look, smell and taste of her little perfect cunt for the first time.

I pushed my finger up inside her and started licking around her clit. It was tucked inside her outer labia but I found it with the tip of my tongue.

It turned out that she did have some little inner labia up there too and I sucked on and teased those while I finger-fucked her. She bent her knees a bit and started thrusting up and down my finger in the same rhythm.

“I need to sit down,” she said. “But I don’t want you to stop what you are doing to me.”

She stepped back to an arm chair and sat down with her legs spread wide open, inviting me to bury my face in her crotch. What a fucking sight. I couldn’t resist that! I crouched down in front of her with my face in her lap and my hands around her waist and small, tight ass.

I licked around her clit for a few minutes and it doubled in size and became engorged as she got more and more turned on. She was grinding her pussy into my face and I could feel that she was breathing more deeply and building towards an orgasm.

And then it happened. We had the fingers of our hands interlocked and I felt her grip tighten first. Then she tensed, her thighs squeezed together on my head and I felt the first pulse of her clit as she orgasmed in my mouth. Eventually she went limp, let go of my hands and sighed a deep sigh of contentment.

“Fuuuuuck. That was….intense. Nobody has EVER done that to me before,” she said, slightly out of breath.

“Wait until you feel my cock inside you,” I said as I picked her up by the waist and moved her forward on the chair so I could penetrate her.

“No! Stop!”

“What the actual fuck?” I thought. “We were going to have sex and after I give her the orgasm of her life, now she wants to stop?”

“I want to suck that cock of yours,” she said. “I’ve never seen a head like that and I NEED to feel what it’s like in my mouth.”

“Geez…you made me think you changed your mind,” I said. “Thank god you haven’t or I think my balls would have exploded. Why don’t we go to the couch and you can see what blowing a real man’s cock is like.”

We moved over to her couch and I sat down with my legs spread and my erection pointed straight up.

She knelt between my knees and put her right hand on my shaft. She slowly lowered her face over my penis and took the head into her mouth. Her tongue circled my head and she bobbed up and down. I moved her hair off to the side so I could see my cock as she worked up and down with her mouth. This was a girl who with a bit of experience in the blow job department!

“I fucking adore what you are doing to me right now,” I said. “But don’t make me cum because I want to fuck you and cum deep inside that pussy of yours.

She didn’t respond. Instead she began working harder as though it was her new goal to make me orgasm in her mouth. I have to be honest…I was pretty close to shooting my load and I’m pretty confident she would have lapped it all up and been quite happy about it. But I really wanted to fuck her now and she could always have another go at that later.

I pushed her head off my cock, grabbed her under her arms and lifted her up, then told her to get on top of me.

“I want to be inside you. Now,” I said somewhat forcefully while grabbing her around the waist and pulling her on top, facing me.

I had one hand on her pussy, spreading her lips with my fingers to make a path for my swollen cock. My other hand was on my shaft, guiding it up to her wet slit. After wiping the head of my penis around her opening to get things wet, she slid down all the way onto me and it was…heaven.

She was tight and warm and very wet. Her little tits and nipples were in my face and her hands were up in her hair as she started riding up and down my shaft.

“Jesus,” I said under my breath. “You are so goddamn fucking hot.”

She rode my cock for a few minutes while I played with her nipples and reached around to explore her ass. She didn’t seem to object so I slipped a fingertip close to her anus and rubbed around between her ass and cunt with the wetness that was dripping from her pussy.

“Oh god…I love it,” she said. “Don’t stop!”

Well that was enough for me. My fingertip found her asshole and I could feel her relax and invite me to start exploring. I gently pushed my fingertip in and the realization that she would probably be fine with anal at some point put me over the edge.

I came hard, with my cum pumping into her pussy and my fingertip in her ass as she squeezed her own tits and stared into my eyes. I could feel the wetness running down my shaft as she slowed down and eventually sat with my cock deep inside her.

We just sat there for a minute looking at each other with a smile on both of our faces.

“Did we just fucking do that?” I asked.

“Matt can NEVER know this happened,” she replied.

“Nope…fuck no. Never,” I said. “He would be too jealous. Poor guy probably never gets any.”

We sat there for another few minutes and the sweat and body heat was mixing with the semen and pussy juices making for a wonderful after-sex musky smell that only lovers can appreciate.

“We should probably clean up,” I said. “Things are a little messy down there. It’s been a few days since I’ve jacked off and I think I filled you up pretty good.”

She reached over to grab some Kleenex from the side table and my cock, now soft, finally fell out of her pussy. We cleaned up and sat around in the nude for a bit thinking about what had just happened.

She was teasing my soft cock while I stroked her nipples, caressed her small breasts and ran my hands through her hair.

“You aren’t bad for a old dude,” she said.

“And you’re pretty good for a little skinny millennial,” I said.

We both laughed and agreed that this beat whatever plans we might have had for the evening had Matt shown up.

By this time my cock was starting to get hard again and she looked down at it.

“Holy crap! It’s ready to go again?” she asked. “I figured at your age you’d be tapped out for a few hours at least.”

“Hey now. I’m not that old, and I’m lying here with a sexy young babe thinking about what we just did. I’m going to be semi-erect for a week!” I exclaimed.

She laughed and slowly brought her mouth down to finish what she had started earlier…

But that’s for another story.

Source: reddit.com/r/sexystories/comments/bu0px9/from_friends_to_friends_with_benefits