Note: this entire story, with all details, names, places, etc. is a work if fiction. Nonetheless, it’s a hot fantasy I have that makes me cum really hard when I live it in my head while I jack off. Enjoy!
My name is Brian and I work as an accountant. I haven’t really had much success with women, but that’s okay because I’m honestly happy on my own. Nonetheless, there is this hot woman at work who I can’t keep off my mind. I’ve become decent friends with her, in that we usually get lunch together and talk all the time at work. As I’ve gotten to know her, I can’t help but feel attracted to her.
Her name is Amanda; she is about 15 years older than me (she’s in her 40s and I’m in my 20s), and I have felt weird about being so attracted to her due to the age difference. She is about 5’9, but always is at about eye level to me at work because she always wears a sexy pair of black heels. She usually wears a pencil skirt with a nice pair of pantyhose that accentuate her long, sexy legs. Her pencil skirt honestly shows off her perfect ass, which I can’t help but stare at any time she goes up the stairs in front of me. For her top, she usually wears a button down shirt, which is tucked into her skirt. The shirt is always strained by her fucking sexy C-cup tits, and I’m always surprised the buttons don’t pop off. She also usually puts on a maroon colored lipstick, which matches her beautiful red hair, which she wears up in a ponytail. She has green eyes, a sexy smile, and an infectious laugh.
She was married to her husband, who unfortunately passed away about five years ago due to lung cancer. Since then, she told me she just hasn’t dated because she has been taking time off from it and is honestly not sure if she wants to find a new partner after her husband. I in turn, have told her about my frustrations trying to date women my own age, who I find immature, and how dating apps have often really discouraged me because of how little success I’ve had using them.
A few years after I’d started working as an accountant with her as my coworker, she one day mentioned to me during lunch at a local sandwich place that she wanted to try dating again. “That’s great, Amanda!” I said, though I was secretly jealous just a little bit. That said, I’d never make a move on her because it would be so embarrassing to be rejected by her and I wouldn’t want to ruin the friendship. Besides, no respectable older woman like her would ever have any interest in a younger guy like me.
“To be honest though, Brian, I feel pretty nervous about it. I haven’t dated in so long; what if I’m not good at it? And I’m honestly still not sure if I feel ready to date.”
“I think it’s normal to be nervous about dating, even if you’re like me and you’ve been trying to for awhile. For what it’s worth though, I definitely empathize about being worried about being good at it or not, considering I’ve only been on like three dates during the past two years. These dating apps are pretty rough, honestly, and when I do get matches, I’m usually pretty disappointed with the women I’ve matched with in terms of their maturity levels. I think you should just go for it, Amanda; don’t worry so much, you’re a quality woman, and men are definitely going to want to date you!”
“You really think so? I mean, I’m still super fucking nervous… and to be honest I had an idea. I don’t want to weird you out though, so if this is a bad idea just tell me to stop and we can talk about something else.”
At this point I was intrigued and wanted to see what her idea was; I honestly didn’t expect what she was about to tell me. “It’s pretty difficult to scare me, don’t worry. What’s your idea?” I asked.
“Well… to be honest…”, she said as she nervously looked down at her sandwich, “I was wondering if… you’d help me practice? You’re my only real close male friend, and I trust you and your honest opinions. To be clear, I mean just a practice date, just as friends, not a real one. Fuck, I’m sorry, this is a stupid idea, let’s just move on and pretend I never mentioned it.”
When she mentioned the idea, I couldn’t help it but my dick jolted in my pants at the prospect of how far a “practice date” would go and everything it entailed. Surely though, she just meant something basic like talking over coffee.
“Haha, no worries, Amanda. Don’t be embarrassed! I’d love to go on a practice date with you. Like you said, it’s just a practice date, and we’re just friends. I’m not weirded out at all. Besides, it’d be helpful for me too because I clearly need the practice for dating women my age as well.”
She looked up at me with her sexy green eyes and her gorgeous smile: “you’d really help me with this? Thank you so much, Brian!” She then stood up and gave me a quick tight hug, and I was thankful that she leaned into the hug such that she wasn’t up against my crotch and therefore didn’t notice my rock hard cock. It didn’t help that her massive tits were pressed right up against me.
“How does tonight sound? I know of a really nice Italian restaurant we can go to. Come to my house around 6:00 PM or so and we can go from there.” She then gave me her address. “Also, one more favor to ask you, but would you mind coming 30-45 minutes early? I need a guy’s opinion about which outfit I should wear.”
“Sure, Amanda, I’ll come over tonight then.”
“Okay, great! I’ll see you tonight!” At this point, she left money on the table for the waiter, stood up, gave me a smile, and turned around and left to go back to work. I could’ve sworn she was swaying her hips more than usual as I stared at her ass on the way out, but it was probably just my imagination and the fact that I still had a raging boner.
Later that night, I drove over to her place, parked on the street, walked up to her door, and rang the doorbell. She answered the door in about 30 seconds or so. It was unusual for me to see her with her hair down, and wearing jeans and a t-shirt: “Brian, right on time! Come on in! I’ll take you upstairs to my bedroom where you can help me pick out an outfit. Also, you look handsome!” She blushed a little bit, but I was glad that she noticed I wore a nice pair of shoes, khakis, and a button up shirt that I had tucked in.
I followed her up the stairs, and couldn’t help but be fixated on her sexy ass, straining against her jeans. Again, maybe it was just me, but was she swaying her hips more than usual? Fuck, probably not, I was just imagining things because I was horny at the thought of her teasing me when in reality she was just walking up the stairs to her bedroom.
When we got in there, she sat me down on the bed, and went to the adjacent bathroom and closed the door while she changed. When she came out 10 minutes later, I wasn’t prepared for how hot she looked. She was wearing a sexy pair of black stiletto heels, a black minidress that showed cleavage from her huge sexy tits, and a necklace made of pearls. She wasn’t wearing leggings or pantyhose, so seeing her bare legs was also a huge turn on for me. She did a spin around, and I saw that the back of her dress had an open back and a zipper that went up it. She was wearing a black lace bra, and my dick jolted in my pants again. “Could you help me zip this up?” She asked. I stood up and did so, while she pulled up her hair so it wouldn’t get caught in the zipper. I then sat back down on the bed while she turned around a couple times for me. She looked so fucking sexy with her breasts pushing against the fabric of the minidress and her ass accentuated by the stiletto heels she was wearing. Every curve of her body was on display, and I was getting desperate to conceal my dick straining against my pants.
“What do you think?” She asked nervously. “Honestly? I think your outfit is amazing.” I paused for a moment and wondered how honest I should be, but Amanda was my friend and I wanted to tell her how I felt about how she looked. “I promise I’m not saying this to be weird, but, honestly Amanda, you look incredibly sexy.” When I said this, her face turned bright red. Fuck, I probably made her pussy wet, and I was getting more and more turned on. I had hid my erection in my waist band at this point and was hoping she wouldn’t notice. “Tha-thank you, Brian” she stuttered. “It means a lot to me for you to say that; I honestly haven’t felt sexy in a long time, not since my husband used to make me feel that way. I have another outfit I’d like to try on, just give me a moment.”
She went back into the bathroom, and she came out again a bit later wearing a new outfit. This time, she was wearing a bright red dress, much looser than the minidress. It was one of those dresses that had a slit up the side (almost up to her hip!). Seeing so much of her legs was really turning me on. She was also wearing a pair of red heels to match the dress, again stilettos (which made me even hornier). She also had on a silver choker with diamonds embedded in it. When she spun around for me, I saw she had no bra on this time(!). Fuck, I was in trouble, my dick wouldn’t be going down anytime soon that’s for sure.
“Holy shit, Amanda, you look fucking hot!” I realized that maybe I’d just been a bit too honest, but luckily she took it well and giggled! “Thank you, Brian, you’re too flattering. So, which of these two outfits do you think I should wear on a real date?” “Honestly? I don’t think it matters, Amanda. You look gorgeous in both of them, and men are going to be knocking down your door when they see you in them. I have a slight preference for the black minidress, but that’s just me. They’re really both great outfits.”
She paused and smiled at me for a second. “Thanks, I really appreciate your honest opinion, Brian. Give me a few moments and I’ll change back into the black one. She went back into her bathroom, and when she came back out later, not only was she back in her sexy black minidress, but she had also decided to put on a pair of black thigh high stockings! She asked me to come help her zip up her dress again, and seeing her black lace bra and her black stockings from the back, I was definitely in trouble. I walked over to her and zipped up her dress for her. I unfortunately brushed my cock up against her ass by accident while I did this; did she just let out a sigh? I was probably imagining things. More importantly, I was very embarrassed and worried she was going to say something. Luckily for me, she didn’t mention it, but when she turned around to face me I could’ve sworn I saw her eyes briefly dart down to look at my crotch before she made eye contact with me again. I must’ve just been horny out of my mind, but I swear she had what I call the “fuck me” smile.
“Okay then! Ready to go to the restaurant?” I drove her over to the restaurant and found parking, walked in with her and sat down. I had calmed down a bit at this point and my dick was semi-hard and much easier to hide. We enjoyed a really nice talk over dinner and shared a bottle of red wine together. When it came time to pay, we reached a brief awkward moment. “So since I asked you for your help, Brian, I would like to pay” “Nonsense, Amanda, I was going to offer to pay because that’s the gentlemanly thing to do.” She seemed to really like my offer, “ooh, a true gentleman,” but she kept insisting that she be the one to pay. Finally I said “you know, most people in my age group just split the bill on dates, especially early on and if they’re not in a relationship. It’s 2021, after all, why don’t we just do that?” “You know, I actually really like that idea! Okay, let’s just split the bill”.
We walked back to my car and I parked on the street outside her house when we reached it. “I had a really good time tonight Brian; you’re a really good friend.” She paused for a moment while looking at me, before she finally said: “… I… I was going to ask you if you could help me again, but this time it’s really embarrassing and personal.” I looked up at her, again wondering what she had in mind. “Look, we’re both adults, Brian, and, well, I’m sure you’re not naïve. Women have needs like men too. Trouble is, I haven’t had sex with anyone since my husband. If I have real dates that go well, I want to bring them with me back inside. You’re my friend, and I really trust you… and… I was wondering if I could have your opinion on some lingerie I own?”
At this point, I was in trouble. My cock was immediately harder than it’d ever been in my life. My brain, which was telling me how bad of an idea this was, how this was weird since she was so much older than me, and how this would almost certainly destroy our friendship, turned off and was no longer functioning. My thought process was completely dictated by my dick. She looked at me nervously awaiting my answer, and when I enthusiastically said “absolutely! I’d love to see you in lingerie” she blushed and smiled at me.
When we got back up to her bed room, she sat me down on the bed and asked “are you sure you’re okay with helping me with this? I just really want a guy’s opinion and I do really trust you, Brian. I just don’t want to ruin our friendship.” “I promise, Amanda, I won’t be weirded out by this, and things between us won’t change. I like being friends with you and I don’t want to let that go.” “Okay!” she said excitedly “wait here.” She then got up and closed her bathroom door while she changed.
When she came back out, I was a goner. Nothing could’ve prepared me with how fucking sexy she was. She came out, still wearing her black thigh high stockings and stilettos, but this time, she wasn’t wearing her minidress. Her stockings were held up by a black garter belt, and when she spun around, I could see that her black lace panties were actually a high-cut thong. Her ass cheeks looked so fucking hot, I could barely contain myself. She had her black lace bra on, but this time I could see just how fantastic her breasts were from the front. “What do you think?” She asked me excitedly.
At this point, I was getting nervous. “I think.. I… I think you look so incredibly sexy, Amanda.” She just smiled back at me. “Okay, well wait here, handsome, and I’ll be right back with another outfit that will really get you going.” Did she just call me handsome? I probably was just imagining it in my mind, which couldn’t even form coherent thoughts. I did manage to wonder, though, what lingerie she could possibly wear that would be able to turn me on anymore than I already was.
She came out again, this time wearing a pink babydoll with a single bow holding it together. She had on a see through pink g-string; was that a landing strip I could see?! When she spun around I couldn’t help but be incredibly turned on by the fact that her g-string disappeared between her ass cheeks. She also had on a pink pair of what I’d call “stripper heels”. My God, I couldn’t take much more of this. “What about this one?” I basically had no control over what I said next. “Fuck.. I… I… I’m so turned on by you and your sexy body Amanda.” I immediately regretted being so honest, but she took it very well and just stood there smiling at me. Was that lust in her eyes? “I can see that, Brian. Thank you, you’re very sweet” She said, looking down at my crotch. “I promise we’re almost done and then I’ll stop getting you so worked up. Wait here, I have one last outfit that I think will blow you away.” At this point, I believed that this would be impossible for her to make me any hornier. I stared at her sexy ass with her pink g-string as she walked back to the bathroom. She totally caught me staring, briefly looking back at me before she made it to the bathroom. She giggled and gave her ass a wiggle.
When she came back out, she was absolutely right. I was completely dumbfounded at how sexy she looked, and how my cock was so hard it felt like it was going to explode out of my pants any moment. She came out wearing a pair of strappy black heels, where the straps went halfway up her legs. She was now wearing a pair of black fishnets as well. The only other thing she had on was a neon orange crotchless and cupless teddy. Seeing her tits completely exposed with her sexy pink nipples fully hard almost sent me over the edge. When I looked down at her pussy, I saw the red landing strip (the same color as her hair) and the sexiest pair of pussy lips I’ve ever seen. She spun around for me, and the neon orange teddy completely disappeared between her ass cheeks, as it was basically a g-string. When she turned back around to face me, what she said completely changed the dynamic of our friendship beyond the point of no return.
“Brian, I had such a good time with you tonight, and I wanted to properly thank you for helping me. This slutty outfit is one I only wore for my husband, I wouldn’t normally wear it after a date. I’ve noticed that your cock has been rock hard all night, and that you’ve been lusting after me. I don’t want to send you home without giving you the opportunity to fuck me any way you please.”
At this point, I don’t even know what I was thinking, but I walked over to her, pushed her against the wall, and started making out with her. Fuck, her tongue felt so good. And she moaned really hard in my mouth. My hands quickly found their way up to her chest, and I started playing with her nipples which made her gasp in pleasure. I also paid attention to her ass and made sure to squeeze it. Meanwhile, her hand had found its way down to my cock and she started rubbing it over my pants. Her other hand was behind my head, playing with my hair while she pulled me into her as we made out.
After awhile of this, she abruptly dropped to her knees, unzipped my khakis, and ripped down my pants and boxers to my ankles. My cock sprung free, flopping around from how abruptly she had taken it out. “Oh my God, Brian, you have an amazing cock. It’s so fucking big! I’m going to give you a night to remember.” And with this, while looking up at me straight into my eyes, she put my balls in her mouth and started jacking me off. I have never felt so good in my life. Seeing her down there and feeling her tongue play with my balls while her hand explored every inch of my shaft was an amazing feeling, and it was so fucking hot that her lipstick was getting all over my balls. I let out an audible moan of pleasure, and she responded by quickly jamming my cock down her throat. At this point, I yelped with pleasure. I couldn’t believe Amanda was gagging on my dick! Her hungry green eyes were so sexy while her lips were pressed against my body and her hand was playing with my balls. She then started effortlessly moving up and down my shaft, gagging each time she deepthroated my cock. I wasn’t going to last much longer. “Oh my God… Amanda… I’m.. I’M FUCKING CUMMING!!” and as I said this, she rammed my prick all the way down her throat. Ropes of cum kept spurting over and over from my cock, and I honestly was surprised with how long this went on. I was also in disbelief that her first instinct was to swallow my cum; holy fucking shit.
When I was finished having the best orgasm of my life, she took my cock out of her throat, and with some of my jizz still in her mouth, she stood up and we started making out again. I have never had a fetish for tasting my own cum, but holy shit, this was the hottest experience of my life while we shared some of it between each others mouths. My cock didn’t even have a chance to get soft, I was still hard as a rock throughout this whole experience. After awhile of making out and sharing my cum between our mouths, she stopped and said “I’m so fucking turned on by you and your gorgeous young cock, Brian. I haven’t felt this turned on since my husband. I’m going to fuck you now because I need to feel your cock inside me. And don’t worry, I had my tubes tied ages ago, so you can just cum inside me.
And with this, she pushed me on my back on her bed. She got on top of me and was straddling me. She had kept her lingerie on this entire time which just turned me on even more. I had managed to take off my shirt and was completely naked by the time I reached her bed. When her pussy pressed against my dick as we continued making out, I couldn’t believe how wet she was. She used two of her fingers to spread open her sexy vagina and with her other hand grabbed my dick and guided it into her opening. She sat down on me slowly, and the only description for the pleasure we both felt was ecstasy. “Oh my fucking God, Brian, your huge dick feels so fucking good. I’m going to ride your brains out.” And with this, she started rapidly bouncing up and down on my cock.
“OH MY GOD! OHHHH FUCK!! YEAH, FUCK ME BRIAN!” She was fucking screaming with pleasure. I had an amazing view as I could see my dick going into and out of her tight pussy. Her tits were bouncing every which way as she rode me, which was so fucking hot that I grabbed them and pinched her nipples. I also started slapping her ass, making her ass cheeks as red as possible. “Oh fuck yeah! Make my ass cheeks red!” She was riding me so hard and fast that my balls were actually painfully slapping against her ass. But I didn’t care because the pleasure far outweighed the pain.
“Fuck. Oh my.. OH MY GOD!!! BRIAN!! I’M… I’M CUMMING!!!!” and with that, she lifted herself off my dick and started squirting. It was all over the place, especially me. When she was done, she went back to riding me. She must have orgasmed at least ten times, but I was so caught up in the unbelievably hot sex that I lost count. She only had squirted during the first orgasm though, while for the rest it was so hot feeling her vagina pulsate and squeeze my dick. Finally, it was my turn. “Holy fuck.. Amanda… I’m going to cum all the way inside your tight vagina. Holy.. HOLY FUCKING SHIT!!” and I started absolutely erupting jizz so hard into her while she moaned “oh fuck yeah, fucking creampie my cunt Brian!” I swear, I orgasmed for a full minute, which had never happened before.
After I had finished, I was still hard. And Amanda noticed “not done yet, huh sexy? I’m going to do something for you that I used to also only do for my husband, he really liked it.” Saying this, she got up off of me, and got on all fours. Fuck, I was going to get to fuck her doggystyle. As she did this, I could see my jizz leaking out of her vagina onto the bed along with her pussy juices. “Brian… I want you to use my asshole for your pleasure… take me and do whatever you want to my tight little ass.” She took out a bottle of lube from her dresser and squirted a bunch on her asshole, and started fingering it. Holy shit, the sight of that alone almost made me cum.
I couldn’t believe what I was seeing and hearing. Again, my dick didn’t get soft after I came because of how fucking hot this whole experience was. I lined myself up behind her, and I slowly started pushing my dick into her asshole. It was so tight, it was nearly impossible to get in, but eventually I had managed to put it all the way inside her. “Holy fuck, Brian, your cock feels so good filling up my ass. I want you to have sex with my asshole as hard as you want to.” Upon hearing this, I started absolutely railing her. I also pulled her hair as I was doing this. In fact, I pounded her asshole so hard, that the bed was loudly thumping against the wall over and over again. The room became incredibly loud with her screams and moans, the bed hitting the wall, my flesh smacking into her, and my balls continually slapping her pussy. It was so hot seeing my prick disappear into her asshole while her g-string teddy was still in her ass crack.
We continued like this for a couple minutes, but even after I had cum twice, I still wasn’t going to last much longer. When I came, I came so hard that I started blacking out. She also came at the same time, and was squirting like crazy everywhere. “OH MY FUCKING GOD, AMANDA. I CANT BELIEVE I’M JIZZING IN YOUR ASSHOLE.” “FUCKING FILL ME UP, BRIAN!! I’M FUCKING SQUIRTING FROM HOW GOOD YOUR DICK FEELS JAMMED UP MY TIGHT ASSHOLE!” I continued to absolutely unleash my spunk into her while her cunt juices were flying in every direction. When I finally pulled out of her, my spunk was slowly oozing out of her down her legs. I can’t believe I had just gotten to fuck her in all three of her holes.
We were finally spent and both collapsed from exhaustion. We both took a shower together, where we continued kissing, but this time it was less lustful and more loving/passionate. “Amanda, I don’t know how to say this but… I love you.” She looked up at me while the water rolled down our bodies. She gave me that look of being so content and happy that my heart just melted. She brought herself closer to me, and looking into my eyes asked me “really? I.. I love you too, Brian.” And we made out for hours in the shower together. When we were finally done, I ended up spending the night. She cuddled up next to me, and neither of us had slept so peacefully in a long time.
That was 32 years ago now. We’re happily married, and still have crazy hot sex together even after all this time.
Source: reddit.com/r/eroticliterature/comments/s2l1aq/sex_with_my_older_friend_amanda_mf_milf_lingerie
Mmm sooo hot
This is a very hot story. Keep it going.
This gets t g e coveted schwing award (5 bonder level)
My cock is So fucking hard, playing this out in my mind!! GREAT WRITING,!!