My Best Friend’s Mom

Ever since I could remember, I’ve been sexually and romantically interested in older women. When I was a freshman in high school, I only dated seniors; Once I hit college, I only dated working women. I could never quite pinpoint exactly why I was interested in them, but I deduced it down to three main reasons. First of all, older women are more responsible and mature. They (for the most part) have their life together and take responsibility for their actions. Secondly, they know what they want. They’re never going to beat around the bush – they’re just going to tell you exactly how they feel. And last but not least, older women are the most sexually experienced. They can teach you a lot about yourself, your taste, and what really gets you off. There’s no shame or fear of judgment – they’re open to it all.

This infatuation with older women has had its upsides, but it’s also had its downfalls. Although I’ve never said anything, I’ve been attracted to so many of my professors, parents’ friends, and even (or, especially) my friends’ moms. I’ve always been the younger, respectful boy, so of course I wouldn’t say anything sexually suggestive. And worst of all, the mom of my childhood friend Ryan was smoking-hot, single, and I’d been dreaming about her for over a decade. I seriously had vivid dreams about Chrissie and I fucking in the back of her station-wagon; I could feel her soft skin and notice the familiar smell of her sweet perfume. Whenever I’d see her while at her house with Ryan, I felt awkward, as if we’d actually fucked before, and it was a secret only I was in on.

Ryan and I would be hanging out in his kitchen and Chrissie would come in and offer to make us food and mixed-drinks. Chrissie was 49 years old, but you could tell from her fit-body, ocean-blue eyes, and long, curly blonde hair that she used to get wild in college as a sorority girl – she was no stranger to making mixed-drinks. And the drinks that she mixed were absolutely delicious. I was always so nervous around her, so I’d down the drinks to feel more comfortable and looser – thinking that Ryan would suspect I was eyeing her down otherwise. These sorts of hangouts would go on for the next consecutive 9 months after we graduated college, which was roughly 2 years ago.

But by the time March hit and spring was approaching, my time with Ryan and Chrissie came to a screeching halt. We’d spent all of our lives in New York – we grew up here, went to state school, and originally planned on working local to home. That all changed when Ryan announced that he’d be moving to Los Angeles to work in entertainment. It was a big shock and change from his original plan to go to dental school, but we all supported him. Though, that meant that I wouldn’t be able to see Chrissie anymore. My beautiful, secret relationship with her (in my head) would come to a curtain close, too. Maybe I was being a bit drastic about this, but despite my major infatuation, I always did get the sense that she would fuck me if she knew how I truly felt. And maybe she felt the same way too.

Unlike Ryan, I stuck around because I was deferring for a year before medical school. After four rigorous years of studying, I felt that I needed a break – a moment to breathe – so I just stayed at home and occasionally helped my parents around the house. I also rekindled with old high school friends and just enjoyed life overall. Despite this enjoyment, I still needed to make money, and I had no viable source of income. I realized it was definitely a good decision to try and save up money for my time during medical school so that I’d be able to live comfortably. Although my home was on Long Island, I’d be going to medical school in Manhattan (and likely living out there), so life could get pricey. With some stroke of luck, it only took one interaction with a familiar face to change all of that confusion and concern. 

I remember it like it was yesterday; It was an incredibly hot day and my parents were having a barbeque with some friends. The ice in their bucket of drinks melted faster than expected so they sent me out on a supermarket run to pick up some more ice. While I was in the freezer aisle, I felt a tap on my shoulder. I turned around, and to much surprise, saw Chrissie, flashing her radiant smile at me. 

“Hi Everett! I thought that was you!” Chrissie said softly.

“Oh, Hi Chrissie! I was so confused, I didn’t know who’d be tapping me on the shoulder,” I said nervously.

“Where have you been?” She asked.

“Just busy with things. Picking up some ice for my parents,” I said.

“Nice. Well, when you’re not busy, you’re more than welcome to come over for a drink. Now that Ryan’s been off to Hollywood it’s been getting a bit lonely. And I definitely need some help around the house – I could pay you, too” Chrissie said sincerely as she smiled.

“Of course,” I said anxiously.

I felt like such an idiot – I didn’t know how to respond in a suave, smooth way. This was such a pivotal, important moment where she finally expressed interest in me. In my mind, there was no way that she wasn’t just hitting on me. As I said before, an older woman like Chrissie knew what she wanted and wasn’t afraid to be blunt about it. Of course, she didn’t flat out say that she wanted to fuck me, but to me, that was pretty much an invitation. But despite my suspicions, I stayed casual and responded in a way that made me still seem like an innocent young man. Then, I bought the ice, left, and went back home – I couldn’t get my mind off of our encounter.

I wanted to take Chrissie up on her offer so badly, but the problem was, I didn’t have her contact information. I was so nervous I forgot to ask her. As much as I didn’t want to do it, I had to ask Ryan for Chrissie’s phone number. So, I texted him casually about how everything was going out in Los Angeles. Then, after the small-talk, I directly asked what Chrissie’s number was. I told him the truth – saying that she offered to pay me for work around the house, and that I really needed the money before starting school. Of course, I had to leave out the part about her wanting to have drinks and feeling lonely. Ryan gave me her number without suspecting a thing. It was easier than I expected (or I was just irrationally nervous).

Then, the actually difficult part was how to take Chrissie up on her offer. I had absolutely no idea what to text her – whether I should acknowledge the drinks and loneliness or just mention the work around the house. I decided to wait for the weekend to pass, and then once I actually decided to send the text, it took me around an hour to concoct. What I came up with was this: “Hey Chrissie, I have some free time this week. So, if you’d like for me to come over and do some work, I can definitely do that. Just let me know.”

In my mind, this text wasn’t too strong, and kept things casual. I figured that if she was actually interested in something more, that I’d clearly see that over time – I could just shift gears and show her that I was interested too. And soon enough, she texted back, inviting me over for that next Wednesday to help her move some furniture around and clean out the garage. Since she fired back with such a casual response, I felt like I might’ve blown my chances at anything sexual – but then I realized that she probably didn’t want to come off even stronger than her suggestions at the supermarket, especially if I wasn’t reciprocating. 

Since I was still not really doing anything with my time, it passed by so slowly from Monday to Wednesday. Each and every day I just sat in my house, played video games, and looked at Chrissie’s text, trying to decipher it – as if it would show some sort of hidden meaning after looking at it 1000 times. I couldn’t wait to just go over Chrissie’s house to see what this was all about – if she was hungry for my touch or was just being friendly and actually wanted work done around the house. 

Finally, Wednesday rolled around and I woke up early to get a fresh start on the day before going over to Chrissie’s house. She wanted me in at 11:00am, so I took the morning to eat breakfast, shower, and shave (both my beard and pubes). I wanted to be ready for anything that life would throw at me later in the day. I drove over to her house and nervously waited at the door after I rang the bell. Now, this was the moment that would determine the nature of her request for me to work. She opened up the door wearing tight Lululemon leggings and a workout tank-top over a sports bra. I couldn’t control myself with how hot she looked – I’d never seen her in clothing that showed off her form so much. And her skin was glistening – I could tell she had just gotten back from a run. In my mind, I thought that she worked out before to look more fit for me. Chrissie led me inside the house to the kitchen.

I couldn’t take my eyes off her jiggling ass as I walked behind her. I didn’t even hear what she was saying because all I could think about was her sitting on my face – with me tonguing her pussy, eating her out passionately. My cock was already rock hard, and we hadn’t even done anything. Good thing I was wearing bulky jeans, otherwise she would’ve been able to easily tell. Once Chrissie sat me down at the kitchen island, she asked me if I wanted any coffee or tea. I’m not a coffee drinker, but I noticed the coffee maker on the counter in front of me – which meant I could stare at her perfectly-shaped ass for longer – so I accepted her offer. I was so overwhelmed with everything, so I couldn’t help but act nervously and irrationally.

I took one sip of the coffee and then asked about what exactly she needed help with. Chrissie said she needed help moving a dresser in her bedroom into Ryan’s room since he wasn’t living there any longer. Was Chrissie just trying to bring me into her room right away and fuck me? Or was I just nervous, delusional, and way in over my head? I suggested we get right to work, and as we walked up the stairs each step felt heavier than the last. I was filled with nerves, thinking this was actually about to happen – but I came prepared with two condoms in my wallet.

All of my nerves settled once she brought me to the bedroom and there was actually a dresser to move. Now, I pretty much confirmed that I was thinking about this too deeply – she liked me as a person and just needed me to help around the house. We moved the dresser into Ryan’s room fairly quickly, but the work wasn’t over quite yet. Chrissie mentioned that she had a ton of storage boxes that she also wanted to move from the garage into Ryan’s room – so I got to it (and Chrissie helped). There were innumerous boxes, and this ended up actually being difficult and taking me roughly three hours to finish. By this point I was sweaty and exhausted – the last thing on my mind was thinking about whether or not Chrissie was into me. 

As I put the final box in Ryan’s room and went downstairs into the kitchen, I noticed the smell of bacon. I was so hungry and couldn’t believe that Chrissie would be eating a delicious meal in my face after all of this hard labor. To my own surprise, Chrissie was actually making me a turkey sandwich with bacon. She told me to take a seat at the kitchen island. Then, she opened up the fridge and handed me a bottle of beer and started to drink one herself. Because of how genuinely nice Chrissie was, I was incredibly turned on once again, despite being a dirty mess. I could feel my sweaty, hard cock pressing against my legs. I tried not to fidget to put it back in place, in fear that she might notice. It was hard to hold my cock in place, so I had to let it just pop up – but I thought my bulky jeans would hide it well.

I started to drink the beer before Chrissie finished making the sandwich – which was both a good and bad idea. Since I hadn’t drank for a bit and essentially just did physical exercise, my alcohol tolerance was really low. So, halfway through the first beer I was already feeling a bit buzzed – but tried to keep myself contained. Then, Chrissie served me the sandwich and took a seat right next to me – I scarfed it down before she even started eating hers. 

“Wow, you must’ve been starving huh?” Chrissie said curiously, with a coy smile.

“Yeah, that was a good amount of work! But thank you so much for the sandwich… and beer. I really appreciate it,” I said softly.

I continued to drink my beer and nearly finished, but I didn’t realize that Chrissie drank hers just as fast. As we drank and ate, I started to feel more than buzzed – almost loopy – while Chrissie and I talked casually about my life, and what I’d be doing for the next few months before medical school, and my plans afterwards. I don’t know if I was just drunk, but it seemed that Chrissie was listening intently, and she wouldn’t take her eyes off of me, although we were less than two feet apart. I noticed that as Chrissie would listen, she’d lick her lips every so often. I couldn’t tell if she noticed, but I couldn’t take my eyes off of them – they were so pink and luscious, I wanted to suck on them so hard. 

Then, Chrissie offered me another beer. I accepted. I could tell that she was trying to loosen me up and get me feeling good, because things seemed to be getting more intimate as she opened up about her life. She spoke more about how she was already missing Ryan and how it would get lonely and quite at the house – how she wished she had someone there to keep her company and make sure the house was in order. She thanked me for coming and mentioned how the fact that I was there didn’t make her feel as lonely. Chrissie then inquired about my relationship status – whether I was in one, when was the last time I was in one, and what I look for in a girl. All of these questions were clear indications to me that she was interested – this wasn’t just casual anymore – and escalated quicker than I expected. 

Since I was getting very drunk, I let go of my inhibitions and told Chrissie honestly that I have never dated a girl my age and I have always been infatuated with older women because of their experience and maturity. Also, that I wasn’t in a relationship at the moment. This was the first major hint to Chrissie by me that I was attracted to her and reciprocating on her interest. I specifically noticed her beautiful blue eyes light up when I told her about this. And those eyes couldn’t keep themselves off of my lips. Without saying anything, we could feel the sexual attraction pulsing and knew that this day wasn’t going to end without us devouring each other’s bodies. 

Chrissie also got a second beer from the fridge (and a third for me) and downed hers faster than the last. I don’t drink often, and when I do, it’s just a beer, or two. But now on my third beer, I was entering uncharted territory – it gave me the liquid courage to keep the sexual tension running high. What felt like an hour passed by, and the conversation was dying down – I just wasn’t sure what the next move would be. If I tried to kiss Chrissie or touch her in any way without her consent or clear interest, that would be very bad. So, I just waited to see if she’d make a move. And like I said, older women know what they want, so they’re not afraid to take that first step, even if it means stepping out of their comfort zone. Ultimately, Chrissie’s actions proved my theory right. 

Chrissie spliced the silence, “I just can’t believe you’re single. You’re such an attractive young man, and you have like no fat on your body.”

Her flattery pierced my heart, “Thanks, you’re very attractive, too. And very in-shape,” I said. 

Chrissie smiled, “Aw, thank you. I bet in all your experience with older women, you’re a pretty good kisser, huh?”

And then, completely out of my control, I said something that would change our relationship forever. “Do you want to try and find out?”

I thought that how direct I was being would startle Chrissie, but she was completely comfortable – almost as if she set me up and expected me to respond that way. Without saying a word, Chrissie leaned in closer to me, until I could feel her warm breath brush against my mouth. She put her warm, wet lips on mine ever so softly – they grazed the surface. Then, she put her hand on my face and kissed me fully. I felt butterflies in my stomach, despite being inebriated. I couldn’t believe that this was happening after all of the years of me fantasizing about Chrissie. She continued to kiss me, and I kissed her back passionately, releasing over 10 years of pent-up sexual desire. Chrissie tasted so good. I couldn’t resist but bite her lip hard every now and then, I had this uncontrollable urge take over me. 

I put my hand on her waist – I couldn’t believe how tight her body was. She really stayed in shape, and it was hard to even get a tight grip on her small waist. At the same time, as we continued to kiss, Chrissie put her hand on my thigh and started rubbing it with a lot of pressure. Slowly, she worked her way into my groin, and then to my cock. Chrissie rubbed her hand over my cock as it stiffened up even more than before, popping up in my jeans. Chrissie breathed down my neck and started to lick it with quick little, shocking licks as she continued to rub me. 

“You’re a big boy, huh?” Chrissie said.

“Am I?” I said.

“Much bigger than my ex-husband. I want to eat it all,” Chrissie said.

I placed my hands under Chrissie’s breasts, cupping and squeezing them. Even for her age, they were so firm and perfect. Chrissie put her hands over mine and squeezed her breasts with me – it was kinky, and I could tell that she wanted to be dominated – wanted me to use my full force. Then, she guided my hand to the bottom of her shirt and helped me pull it off. Her sports bra came off next. I squeezed her large breasts and rubbed my thumb gently over her sensitive nipples. They hardened. Chrissie and I stood up and I leaned into her, pressing her body against the kitchen island. As I continued to hold Chrissie’s breasts, she reached down once again to my hard cock and stroked it over my jeans.

I could tell that Chrissie was expecting me to take control and fulfill her desires, without her having to ask, so I began licking around her breasts. I slobbered all over her breasts and slowly licked closer and closer to her hard nipples. Her skin tasted so sweet. As I was licking and sucking her nipples, she sneakily unbuttoned and unzipped my jeans, pulling them off. I didn’t even realize what was happening until her soft, warm hands gripped my cock and started stroking it. Chrissie was clearly a pro with a lot of experience – I was about to cum with her just touching my cock with no lubricant or lotion (except for a lot of sweat). But I held it in so we could both reach a climax.

To match Chrissie, I slyly pulled off her leggings while I was kissing her, and she was rubbing my cock (which was harder to do than I expected). I could see how wet she was from a stain on her underwear. I was just as wet with pre-cum beginning to drip from my cock and onto her kitchen floor. Her legs were so long and smooth, and her pussy was clean-shaven. I put my hands on her thighs and spread her legs, getting a peek of her pink lips. I wanted my lips to kiss her pussy lips and get her full taste. I got down on my knees while Chrissie kept her legs spread and licked her inner-thigh, eventually closer to her wet pussy. As I licked up and down slowly and French-kissed her pussy, I got even harder tasting all of her. I put my entire tongue deep down her warm pussy and wanted to keep it there forever. She grabbed my hair and pulled it, then guided my tongue up to her already-hard clit. Her clit was so large and hard, it was easy to find and incredible to lick because of how weak I could see it was making Chrissie feel.

Once she couldn’t handle the feeling anymore, I reached down into my pants and grabbed the condom I had brought. Good thing I prepared for this moment. I ripped the package off with my teeth and Chrissie took the condom from me. She slid it over my cock and rubbed my cock with a few hard tugs before I slid it inside her wet pussy. I propped Chrissie up onto the cold, granite kitchen counter and stood up with my warm body against her and her legs wrapped around me. Chrissie took all of my long, fat cock and clenched her teeth together in pain – despite her experience I don’t think she had ever taken a cock as big as mine. I could tell that she was enjoying this more than anything before. As I started to thrust into her slowly, she grabbed my hard arms. 

“Fuck me! Destroy my pussy, young man. I’ve been waiting for this for a long time” Chrissie screamed. 

“I’m gonna fuck you like you’ve never been fucked before,” I said with my eyes locked on her, sweat pouring everywhere. I couldn’t believe that she wanted to fuck for as long as I had, my fantasy was quickly becoming a reality. 

I slid my long cock in and out and Chrissie with all of my force and pressure into her little body. I wanted to be as rough with her as she wanted me to be and break her body with my cock. As I picked up the pace, I was thrusting into Chrissie like an animal, holding nothing back. Her body shook and her breasts jiggled uncontrollably. With each thrust Chrissie would make a sharp screaming noise, but she didn’t want me to stop, pulling on my arms to bring me in closer. I brought my face to hers as I continued to thrust, and our tongues wrestled passionately. It was hot for me to think that she was also tasting her own pussy off of my mouth. It came to a point where I just couldn’t hold my cum in any longer. I didn’t expect it to happen so quickly, so the only warning I could give was heavy breathing and me biting Chrissie’s lower lip as hard as possible. 

I came harder than I think I’ve ever cum before. I pulled out of Chrissie and the condom was filled with cum – even more than it could handle. Chrissie wanted to see it too, so she rolled the condom off of me and held it in her hand, looking at all of the cum in awe. She was clearly happy with the product of her hard work – knowing that she was able to turn a young guy like me on so much and get me to cum more than ever. I didn’t want this to just be about me, but Chrissie said that pretty much no one has ever made her cum and that I shouldn’t feel bad about finishing without her. After a few more minutes of kissing and rubbing our bodies against one another, we put our pants back on and Chrissie offered me some ice water.

As we drank our glasses of water and sat on Chrissie’s sofa, I felt pure calmness, like I was in heaven. I was immediately so comfortable and wasn’t weirded out in the slightest by what we had just done (or, me having sex with my best friend’s mom). And she seemed completely comfortable with it too. We went back to talking about everyday things and carried on the conversation as if nothing had just happened – as if it wasn’t a big deal. I realized that this was because Chrissie was mature enough to keep this as something isolated and private. I would do the same – no one would ever hear of this experience. 

So, for the next few months while I was still on Long Island before medical school, I’d occasionally help Chrissie out with “moving furniture”, but it never extended into any other area of my life. No one around town (or Ryan) would ever find out about what happened between us. To us, I was the young stud who would make her feel blissful, but to everyone else, I was just her son’s best friend.