[FF] My best friend’s boyfriend pissed me off, so I [18F] fucked his mom [late 40s F]

The summer after graduating high school, I was in a pissy mood. Yes, the whole summer. I was terrified about going to college hours away from my family and sad to be leaving my friends, especially my best friend, Jillian. Throughout high school, Jillian and I had a covert romantic and sexual relationship. We saw each other intermittently from our first year of high school (age 14) until we left for college (age 18), pausing only when we had boyfriends. And occasionally unpausing it during those times. We somehow simultaneously thought of each other as our soulmate and also a relationship that didn’t “count” as cheating because we were both women. It’s not something I’m proud of, but it’s something I’ve since learned is actually fairly common amongst closeted teenagers.

Our last semester of high school, Jillian started dating a boy in our year named Tom. At first, I didn’t dislike him any more than I disliked her other boyfriends — it was more a general jealousy that she could date them in public instead of an actual dislike of them as individuals. But then, against my wishes, she told Tom about us one night shortly before graduation. I was fucking pissed. I wasn’t ready to be “out,” and I wasn’t even sure what my sexuality was, so this felt like both an invasion of my privacy and a lot of pressure to suddenly define myself. Jillian apologized profusely when she saw how upset I was, and I did forgive her fairly quickly considering my ability to hold a grudge, but the damage was done.

Tom became insufferable. Every time the three of us were in a room together, he would “jokingly” ask us for a threesome as the literal embodiment of what is now known as the “haha jk… unless” meme. Any time he and I were left alone, he would goad me. He’d grab his crotch over his pants, tell me how big his dick was, or say that he could make Jillian cum harder than I ever could because I was just a “dyke with small hands and no cock.” I told Jillian about these things, but she kept laughing it off, saying he was just playing around.

To protect myself from getting slapped with a murder conviction, I avoided him as much as possible, which wasn’t easy considering he was always fucking there: at beach week, at Jillian and my joint graduation party, at Jillian’s side whenever we had plans to hang out. He was determined to prevent us from being alone. I empathized with his concerns because it was true that Jillian had cheated on boyfriends with me in the past, but I was baffled by this dynamic. Why the fuck would you date somebody who you worried would cheat on you the second you left them alone? And why the fuck would you date somebody who didn’t trust you enough to leave you alone for more than a second? Jillian refused to set boundaries, saying she didn’t want to be put in the middle of it. Tom then started insisting on hosting all our friend group hangouts that entire summer, forcing me to be around him if I ever wanted to see my other friends as well.

To be fair, his house was awesome. His mom had gotten an incredible settlement when his dad violated their prenup and ran off with some Pilates instructor, and she poured a lot of the money into renovating the house. The scandal was the talk of the town when it first happened, and I remember my parents going out of their way to bring her dinners and support her as a newly single mom. She ended up not needing anybody’s help. She lost at least 40 pounds, got some work done on her face, and bought herself a fancy car and a whole new wardrobe.

I was honestly floored by how well she handled the divorce in the face of vicious public speculation. She went from being a typical, dumpy small town mom to a hot divorcée in the span of a couple months, and, if the rumors were true, she was taking advantage of her newfound singlehood by constantly going out on dates in town, zipping around in her fancy car with a new guy every time. I’d be lying if I said I hadn’t taken a peek at her when we were all hanging out by their pool, but I still wasn’t quite sure if I was interested in sleeping with women overall or just Jillian. Either way, she was undeniably attractive.

One hot July afternoon, Tom’s mom was inside while the whole friend group lazed around by the pool. Tom was showing off on the diving board for Jillian while I was reapplying sunscreen and struggling to reach my back. “Jill, could you help me out please?” I asked, genuinely innocently.

She took her eyes off Tom and squirted some sunscreen in her hands, rubbing it into my shoulders. When Tom resurfaced, he looked over for Jillian’s approval and saw her hands on me. He immediately shot out of the pool and stomped over to us, grabbing the sunscreen out of Jillian’s hands and shoving his body between us. “I’ve got it, Jillian, you don’t have to do this,” he hissed.

Nevermind the fact that I had no interest in letting him touch me. He forcefully rubbed sunscreen onto my shoulders and back, ignoring me when I asked him to soften the pressure. Jillian left to jump in the pool, throwing her hands up in frustration. Coward. I grit my teeth and bit my tongue, determined not to give him the satisfaction of making a scene in front of our friends. It was the one thing he knew he had over me; Jillian and I weren’t out to the friend group, and he knew that as long as he didn’t cross a line, I would never tell him off in public out of fear that he would out me. That might seem silly from today’s perspective, but this was a decade ago — before same-sex marriage was legalized, before President Obama had even publicly changed his opinion. Especially in a small town, being outwardly queer was something that at best got you ostracized and at worst got you disowned or beaten.

Our friends didn’t seem to notice anything was wrong. They were too busy playing chicken in the pool or flirting amongst themselves or reading trashy magazines. Tom took advantage of their distraction to start whispering to me as he forcefully rubbed in sunscreen. “Nice try, Lily,” he muttered under his breath, “but you’re gonna have to do better than that.”

“What the fuck is your problem, dude?” I whispered, “Jillian isn’t going to cheat on you. We’ve both made that very clear.”

He scoffed. “Obviously. Why would she go for you when she could have my thick cock?”

I made a noise of disgust, but he kept talking. “The offer still stands for you to join us, though,” he murmured, brushing my hair over one shoulder seemingly to apply sunscreen but really just to breathe in my ear, “I’d love for you two to play in front of me.”

One of his hands slid over my shoulder to rub sunscreen on my sternum. I tried to shrug him off, but he held me firm. “Please let go of me,” I whispered, struggling to keep my voice even.

Tom’s hand brushed against the line of my bikini top. “You’ll like it better when a man is involved. I’ll remind you how much you need cock.”

One of his fingertips slid half an inch under my top. That was it. I elbowed him hard in the throat and immediately shot up, rearranging my face to one of playful chagrin and raising my voice for everyone to hear. “Oh my god, Tom, I’m SO SORRY!” I giggled, “I’m so ticklish, it was just an automatic reaction! That’s sooooo embarrassing. I’ll go get you some ice.”

I flounced towards the house as he struggled to breathe, his hand grasping at his throat. Jillian watched me go, concern etched onto her face as she got out of the pool to check on Tom. Fuck her. Fuck that. I was fucking done with Tom’s insecurity and constant power plays, even if I had to come out publicly just so he wouldn’t have anything on me. I slammed the sliding glass door shut harder than necessary and stormed upstairs to the shower. I needed to wash off the feeling of his hands. As I reached the second floor landing, I nearly ran into Tom’s mom. “Oh! Hi Lily!” she said, her kind eyes crinkling as she smiled, “Are you having a nice time?”

How the fuck could somebody as awful as Tom be half made up of her DNA? “Hey, Mrs. S,” I said in a peppy tone, overcompensating to hide my anger, “I was just coming up to wash my sunscreen off. I was getting itchy.”

“Please, Lily, call me Pam. I’m also not even ‘Mrs. Scott’ anymore,” she winked.

“Right, shoot, sorry, Pam,” I said, smiling softly.

“Tom’s bathroom is free, but I don’t think it’s clean enough for guests. Would you like to use the shower in the master bath?”

“That would be amazing, thank you so much.”

“There are towels in the cabinet. Please help yourself to any of the soaps and supplies!”

“Thank you — that’s really nice of you.”

She rubbed my arm gently. Goosebumps erupted in the wake of her touch, and I suddenly felt very exposed in my bikini. “You know I’ve always been fond of you, Lily. I always hoped you and Tom would get together, not that Jillian isn’t a sweet girl, of course.”

I couldn’t stop myself from laughing, and her look of confusion made me laugh harder. Shit. I needed an excuse. “Tom isn’t my type,” I explained weakly, trying to rearrange my face into something more casual and polite than abject disgust.

Her eyes widened. Fuck. She definitely thought I was a lesbian. She quickly recovered, smiling at me. “Then I hope you find someone who is,” she said genuinely, rubbing my arm again, “You seem like somebody who has a lot of love to give.”

She squeezed my hand and then walked down the stairs, leaving behind the scent of lavender and chlorine. That definitely could have gone better. Well, at least she wasn’t one of the more gossipy moms, having been the recipient of some nasty rumors after her divorce and proven herself to be above it all. Besides, Tom was probably already posting a Facebook status about my sexuality as revenge for the elbow to the throat. Comparatively, his mom’s suspicions were barely an issue.

I took my time in the shower, scrubbing at my skin with a loofah until it was rubbed raw. I then grabbed a fresh towel from the cabinet and wrapped it around myself, standing in front of the mirror and surveying Pam’s fancy skin creams. A light knock on the door startled me. “Lily? You find everything ok?” Pam called through the door.

I opened it and smiled at her. “Just snooping through your fancy skincare options! Which do you recommend for minor sunburns? My face looks a little red.”

She smiled back and stepped around me into the bathroom, picking up and putting down bottles as she looked at the labels. I watched her intently. Fuck, she was beautiful. Her face was the epitome of quiet dignity and kindness, like Lindsay Duncan or Helen Mirren. I found myself raking my eyes down her body. “This one is great for sun damage,” she told me, squeezing some of the cream onto her finger and dabbing it across my cheeks.

She paused for a moment and smiled at me. “You have such beautiful skin,” she said softly, “I miss having that youthful complexion.”

“Are you kidding?” I laughed, “I would kill to look like you now, let alone when I’m a mom to a teenager.”

“That’s sweet of you to say.”

“I mean it, Pam. You are absolutely gorgeous.”

She waved off the compliment. “It’s nothing other than the magic of a good dermatologist and flattering clothing. You should see how much loose skin I have from losing weight.”

“I find it hard to believe that any inch of you isn’t beautiful.”

I knew I was crossing a line with my shameless flirting, but I couldn’t bring myself to give a shit. She already suspected that I was attracted to women; if she was uncomfortable with it, then she wouldn’t have come into the bathroom after she saw I was half naked. She flushed, looking away from my intense gaze and screwing the cap back on the cream. “All done. How does that feel?”

“It feels great,” I said, still looking at her, “but I’m afraid I forgot my clothes downstairs.”

She noticeably swallowed. Interesting. Her eyes flickered down to where my cleavage peeked out over the towel. “You’re more than welcome to raid my closet,” she offered, “I’m sure I have some options that are close enough to your size.”

“Thank you so much, Pam,” I murmured, running my hand down her arm and squeezing her hand, “Would you mind please pointing them out to me?”

She led me into the master bedroom and pulled a couple options out of her walk-in closet, hanging them over the edge of a nearby armchair. I intentionally stood a little too close to be casual, letting the slit in the towel wrap reveal most of my upper thigh. Might as well go for broke. “I’ll leave you to get changed,” Pam said softly, not meeting my eyes and heading towards the door.

“You don’t have to go,” I murmured the second her hand touched the doorknob.

It was a hail Mary. Sure, I could have just slept with one of my guy friends again, but I was missing Jillian, missing the exquisite flavors and soft moaning of a woman coming apart against my tongue. It had been over two months since I had last tasted Jillian, the longest we had ever gone without sleeping together since we were 14. I thought Pam was going to laugh me off or give an excuse, but instead she closed the door with a soft click and locked it, turning towards me slowly and bringing her eyes up to meet mine. I smiled at her, holding her gaze and untying my towel. It fell to the ground. Her eyes raked up and down my naked form, her lips parting slightly. I walked towards her slowly, pulling my wet hair over one of my shoulders. Her hand gently stroked my hair once when I reached her, her eyes wandering over my eyes, my smile, my tits. I took one of her hands and gently guided her over to her bed. “I haven’t done this since college,” she murmured.

“I’m sure things haven’t changed too much since then,” I teased, “it’s like riding a bicycle.”

She let go of my hand as I sank down onto the bed, not meeting my eyes and playing with the hem of her pool sarong. “I also haven’t been with anybody since my husband left.”

My eyebrows shot up in surprise. “I thought you’ve been going on all these dates!”

“I have, but I didn’t let them go anywhere.”

I took both her hands in mine. “I would be honored to be the first to welcome you back.”

She laughed and squeezed my hands. We stared at each other for a moment, smiling softly. “Are we really doing this?” she asked, her cheeks flushed.

I leaned in until my lips were almost on hers. “Yeah, Pam, we’re doing this.”

She closed the gap, her soft lips pressing gently against mine. I let her take the lead, but I couldn’t resist dropping her hands to slide my fingers slowly down her back until they were cupping her ass. She leaned into the kiss, pushing me down until I was laying flat against the bed. Her hands cupped my tits, teasing my nipples with her thumb. I quietly moaned into her mouth.

Emboldened, she kissed down my neck until one and then the other nipple was in her mouth. She flicked her tongue forcefully against each one in turn, eliciting another series of moans. I spread my legs so she could settle between them. Painfully slowly, she then kissed and licked her way down my stomach until she was finally at my pussy. She looked up at me. I nodded. She devoured me with her mouth, her enthusiasm taking my breath away. Jillian was the only woman I had been with at that point, and I was used to her small, gentle movements. Pam, on the other hand, was wild.

Her tongue lapped at my clit aggressively, and she unhesitatingly shoved two fingers deep inside of me, immediately finding my g-spot and punishingly rubbing it. I moaned loudly and tangled a hand in her hair. “Oh oh oh!” I shrieked, “Don’t stop! Oh my god don’t stop!”

She smiled against my pussy and continued her relentless licking, her fingers fucking me roughly. The slick, sloppy sounds of her mouth on my clit and her fingers pulsing in my cunt filled the air, the obvious lewdness of the noises making me blush. I pinched one of my nipples and ground my pussy against her face. “Pam,” I groaned, “I’m getting close.”

Pam hitched both my legs over her shoulders and increased the pressure, her whole mouth and tongue rubbing against my clit and a third finger joining the pounding in my cunt. In less than a minute, I was there. I couldn’t stop myself from screaming as I came, my hand holding her face in place and my body shaking violently against the bed. She worked me through my peak, only slowing down when my shrieks returned to quiet moans. She collapsed next to me on the bed, both of us panting. “Are you sure you haven’t been practicing daily?” I teased, “Because holy shit.”

She laughed and wiped the back of her hand across her mouth. “It was definitely better than riding a bicycle.”

I turned on my side and propped myself up on my elbow, my hand brushing her hair away from her face as I forced her to meet my gaze. “Is that how you like it?” I murmured, “Rough and sloppy pussy eating?”

Her eyes searched mine, and she bit her lower lip. “Actually, I prefer it soft and gentle. At least at first. My husband liked it rough, so I guess I was just used to giving with aggression.”

“I can do that,” I murmured, leaning down to kiss her.

My tongue moved against hers slowly, and I gently unwrapped her pool sarong. Both her hands tangled in my hair. I rubbed her pussy softly, teasingly over her swimsuit, slipping my middle finger between her lips. She moaned into my mouth, her hips lifting to increase the pressure. I pulled my hand back and ended the kiss. “Don’t be greedy,” I teased, and then I bit down gently on her lower lip.

We centered ourselves on the bed. I slid my body over hers until I was straddling her, my bare pussy hovering over her hips. I untied the top of her bathing suit. Pam lifted a hand to stop me. I paused. Her eyes danced over my face nervously as she spoke, “I meant what I said earlier. I don’t have a young woman’s body. I’ve carried a baby, and I’ve gained and lost a lot of weight over the years.”

I smiled softly and kissed her gently, gliding my tongue against her lower lip. After a moment, I pulled back, looking her in the eye. “I’m ready when you are.”

She helped me remove her one-piece bathing suit. I let it fall to the ground, devouring her with my eyes. “Holy shit, Pam,” I murmured, climbing back over her to straddle her thighs and rubbing my hands up her body, “You are so fucking sexy.”

Yes, she had stretch marks, and yes, she had loose skin. And her body was incredible: every inch a testament to the full life she had lived and all the experiences she had, including two unexpected little music note tattoos over her hipbone. I leaned over and kissed her again deeply, exploring her mouth with my tongue as I gently trailed my fingers back down her body until they were between us, teasing her pussy with feather-light touches. I again slipped my middle finger between the lips of her pussy, lightly circling her clit. “I’m going to take this slow,” I whispered in her ear, “because I want you to be wetter than you ever were with your husband by the time I finally taste you.”

She panted roughly, her whole body flushed as she stared at me, her eyes darkening. She nodded, her mouth open slightly. I kissed her slowly, my mouth moving against hers as I massaged her tongue with mine. Our kisses got sloppier, lazier, but I kept my finger’s gentle circling of her clit consistent. Eventually, I detached my lips from hers and began kissing up her jaw, placing firm kisses along her skin until I reached her neck. I slid my finger down to tease at the entrance to her pussy. “We’re getting there,” I murmured in her ear, “but I want you to be fucking dripping.”

She moaned, and I moved my finger back up to her clit. Slowly, I kissed down her neck, sucking lightly on her skin, and I kissed along every inch of her chest before I finally touched her breasts. Cupping one of them with the hand not teasing her clit, I lowered my mouth to take her nipple into my mouth. I flicked my tongue against it once and then sucked hard. Pam moaned, her hips bucking up against my finger. I sat down on her thighs to prevent her from moving too much. With a final hard suck, I released her nipple from my mouth, swirling my tongue around it once while maintaining eye contact with her.

Moving to capture her other nipple with my mouth, I dipped my finger again to tease at her entrance. I sucked her nipple as I finally pushed my finger inside, curling it to press against her g-spot. I was surprised by how tight she was; I wasn’t sure if I could even fit more than two fingers inside her. She moaned loudly. I smiled to myself and removed my finger. Slowly kissing down her body, making sure to give every inch of her skin attention, I pressed against her clit with my thumb and started rubbing it roughly. Her moan transitioned into loud, heavy breaths. She propped herself up on her elbows to watch my movements.

As quickly as I started, I stopped rubbing her clit. Her brow furrowed, her heavy breaths visibly making her chest rise and fall. “Patience,” I whispered, smirking at her.

I pulled her legs over my shoulders and kissed up her inner thigh, nipped at her labia, swiped my tongue over her clit once, and then kissed down her other thigh. She brushed my hair back from my face, watching me intently. Slowly, punishingly, I buried my face in her pussy and pushed my tongue past her entrance. She moaned loudly, laying back against the bed. She tasted incredible. Lavender, pussy, a hint of chlorine from the pool, and something else unique to her. I swirled my tongue inside her, moaning, my eyes closed. Fuck. I would have lived off the taste of her cunt if I could.

Reluctantly, I tore myself away and sucked her clit into my mouth, gently rolling my tongue against it. At the same time, I brought my pointer finger to tease her entrance, dipping inside once to the knuckle and then bringing it back out again to circle the rim. “More,” she whispered, her hands clutching at the bedspread.

I kept the pressure on her clit the same, but I pushed my finger back inside her, curling it to gently rub against her g-spot. She moaned, long and low. “More,” she whispered again, demandingly.

I increased the pressure on her clit and pushed in a second finger, massaging her gently with my fluid strokes. One of her arms reached up to cover her face while her other hand tangled into my hair, pushing my face down harder against her warm, beautiful pussy. I obliged, sucking on her clit and flicking it rapidly with my tongue as I began fucking her cunt. Her body rose up against my face. “More!” she called out, her moans reverberating in my ears.

Fuck it. I shoved in a third and fourth finger in one movement, devouring her clit and pressing my nose into her mound, shaking my face back and forth to get closer. My fingers punishingly pounded into her pussy. Her moans turns into shrieks, and I felt her cunt clench around my fingers as she started to orgasm. “Oh my god. Oh my god!” she screamed, her hand pressing against me until I could barely tell where my face ended and her pussy began, “I’m cumming! Don’t stop!”

I wouldn’t have dared. I was having too much fun fucking her warm cunt and lavishing her clit with attention. Her body shook hard against my face, her fingers digging into my scalp and her thighs clenching around my ears. I moaned into her pussy. I kept up my movements, determined to prolong her orgasm as long as possible. Eventually, her loud, deep moans transitioned into softer, shorter sighs, and her body relaxed into the bed, her pussy still occasionally pulsing in waves around my fingers. I slowed my movements and stopped, removing my hand gently and pressing a couple final licks against her clit with a flat tongue.

As soon as I ducked out from between her legs, she curled in on herself on the bed, spasming gently from the aftershocks. I spooned her tightly. Peppering soft kisses over her shoulder, I murmured soft words of encouragement. Regardless of the strength of her orgasm, her first time having sex (and with a woman no less) after her divorce was bound result in a confusing mixture of emotions. She lifted an arm so I could slide mine against her stomach, and then she laced her fingers through mine. “Wow,” she whispered.

I nuzzled my nose against her neck and then settled down against the bed. “How do you feel?” I asked softly.

“The good kind of strange. I wasn’t exactly expecting this.”

I laughed. “Understandable.”

We cuddled on the bed for a while. The feeling of holding her in my arms and knowing I provided her with a positive reentry into her sex life was incredible. Eventually, she shivered, the heat from my body not enough to warm her bare skin against the air conditioning. She untangled herself from me and sat upright. “Thank you,” she said softly, not looking at me.

“It was very genuinely my pleasure.”

She laughed and turned around, brushing my hair away from my face. Her brows furrowed slightly. “You’re my son’s age,” she said softly.

“And?”

“And you’re his friend.”

“Define ‘friend.'”

She laughed. “I know he can be a piece of work, but I don’t want to make life more difficult for him. He took the divorce really hard. He hasn’t even seen his father since it happened. Could you — could you please not mention this to him?”

I captured her hand and pressed a firm kiss to her palm. “Of course.”

Slipping on some of her clothes, grabbing my bikini, and stealing a final, searing kiss, I headed downstairs to rejoin my friends, a small smile on my lips from this new little secret. I still wasn’t sure what I wanted to call myself, but I knew I had to make as many women cum as possible the second I got to college. Jillian stopped me right inside the entrance. “Lily! I didn’t know where you went. Are you ok? Tom finally told me what happened.”

“Yeah. But your boyfriend is the worst. I mean, fuck, Jillian, he is the ACTUAL worst. You deserve better. It is horrifying to me that you let him treat me the way he does, but it is even worse that you let him treat you like you’re property.”

“I don’t—”

“Yes. You do. You let him treat both of us like his personal playthings. And I fucking hate that you gave him leverage over me. I love you, Jill, but that was fucked up.”

She was speechless for a second. “I— I don’t know what you want me to say, Lily. I’ve already apologized for that.”

“I know you have. And I don’t know if I even want anything from you right now. I love you, and I will literally always be here for you, but I’m not going to be with you again until you know more about who you are and what you want.”

“Ok.”

I kissed her on the cheek and walked outside. Tom looked over at me angrily but didn’t say anything, his hand instinctively coming up to rub his throat where I had elbowed him. I smiled pleasantly, laying back on the pool chair and playing on my phone.

Tom left me alone for the rest of the summer. I never told him about the afternoon I spent with his mom, no matter how satisfying it would have been to rub his smug homophobia back in his face. It just wasn’t his business. And it wasn’t my place to out her as bisexual or flexible or however she identified.

Pam ended up getting remarried after I graduated college — actually to the widower father of one of our other friends, James. I’m not sure if Tom ever felt guilty about his behavior, but I like to think that an example of healthy masculinity in his life taught him how to work through his insecurities rather than try to control women. I occasionally run into Pam around town whenever I visit my hometown, and she is always warm, hugging me tightly without hesitation and asking me hundreds of questions about my life. She told me once about a year after our afternoon together that I helped her feel confident enough to genuinely reenter the dating pool, and I told her that she helped me feel comfortable pursuing real relationships with women. It was still another couple years before I came out to my family, but I still credit her with kickstarting the process.

Jillian thankfully dumped Tom a couple weeks before we left for college. She said it was because she didn’t want to do long distance, but I think she was just saving face and feeling embarrassed about finally realizing how poorly he was treating her. I only ended up sleeping with her one more time, but that’s a story for another day.

Source: reddit.com/r/gonewildstories/comments/hfykc5/ff_my_best_friends_boyfriend_pissed_me_off_so_i