Roxy had been Mom’s girlfriend for a couple months. They knew each other from work, how long I didn’t know but it must have been pretty long. Mom had never mentioned her before, and suddenly one day they went out somewhere after work and didn’t come home until almost midnight. I was in bed when they came giggling through the door, trying to whisper. From my bedroom I heard them flop onto the sofa, then I only heard soft moans and kissing sounds for a while. I really wanted to check out Mom’s new girlfriend, but didn’t dare ruin their moment. At some point they moved to Mom’s bedroom, and in the morning Roxy was in the kitchen frying bacon when I got up.
But like I said, that was a couple months ago. I wasn’t disappointed when I laid eyes on Roxy, she had a warm milfiness, an easy smile, and twinkling eyes. I was happy for Mom, here eyes twinkled when Roxy was around, too.
It seemed perfectly natural for me to lust after Mom’s girlfriends. I’d dated just a few girls in High School, both in my Senior year which had just ended. Both of them had been kind of disappointing – very hot looking girls, but not very bright and not very interested in sex. Not with me, anyway. So my sex live existed exclusively in my head, and the objects of my lust had been mostly Mom’s numerous girlfriends over the years, plus one or two of my teachers.
One warm Saturday afternoon in June when Roxy came over to the house. “Is Julie home?” she said.
“Not yet, she should be here soon, though. Come in.”
“She called me a few minutes ago to invite me out, so I came right over.”
We sat on the sofa, Roxy on one end, me on the far end, a little nervous since this was our first time alone together. That, and I was a little embarrassed at how many times I’d lain in bed whacking off thinking of her.
“Your mom’s so proud of you, Jim,” she said, smiling. “She’s so lucky to have a son like you.”
“How do you mean?”
“Oh, you know. You’re so accepting of your mom’s lifestyle. I feel really comfortable being here, thanks to you.”
I’d never said anything about it, and wondered what I might have ever said or done to make her say that.
“She talks about you so much. Says she used to worry what you’d think, but she says you’re one of those kind of guys who loves women like us.”
I shifted in my seat to hide a slight erection. I must have been turning red, too.
“Don’t be embarrassed, sweetie. You’re a man, now. You have your lusts and fetishes like anyone. Never be ashamed of it.”
I tried to smile, hoping Mom would get there soon and end this awkward situation. Then, my phone rang.
The screen said it was Mom. “Jim, honey, is Roxy there yet?”
“Yeah, she’s here.”
“Could you tell her I’m running late, please?”
“Sure. She’s running late,” I said, looking at Roxy.
“How late?” Roxy said.
“I don’t know. It’s traffic. Something’s got it all blocked off. I’ll call you later when it starts moving.” Now I was starting to sweat. Stuck here for who knows how long, with my mom’s hot lesbian girlfriend, and she wants to talk about my sex life. This can’t possibly go well.
Standing, Roxy said, “Well, I’m getting a beer. Want one?”
“Uh, yeah I’d love one, but I’m not- ”
“Oh, shut up. You’re old enough,” she said as she sauntered into the kitchen.
I watched her hips sway, remembering how I’d dreamed of grabbing that very ass and drilling her so many times.
She came back with two open bottles, handed me one, and sat down. This time, somewhat closer to me than before.
I shifted on the upholstery again, and looked out the front window. Maybe mom will show up any second.
“Where were we? Oh yeah, your fetishes. Would you stop blushing, for God’s sake? Why be embarrassed?”
“I- ” Looking into her eyes, something changed in me. I was so charmed by her smile, the warmth in here eyes, something unidentifiable in her manner.
She must have seen me relax. She uncrossed her legs and shifted maybe an inch closer to me in the process. “That’s more like it.” She leaned toward me. “So what’s your favorite thing about a girl?”
Drawing in a breath, I thought about it. Boobs? Ass? Eyes? “I think, just holding her close and feeling her body against mine.”
“I like that, too.” She took a swig from her bottle. “But it’s not my favorite thing. How far have you been with a girl?”
I though of my last attempt. “Kissing, heavy petting, that’s about it.”
“Ah, those are awesome. I see you have a lot of great stuff to look forward to, though. But, take my advice – enjoy every minute of the stuff that leads up to the actual fucking. Orgasms are good, but they’re just the icing on the cake. Don’t focus on coming and forget to enjoy the cake, too.”
“There doesn’t seem to be any danger of focusing too much on that.”
She smiled. “The thing that’s so cool about Julie, she really wants you to have a good sex life. Did you know that? Oh, don’t blush on me again.”
“No, I didn’t know that.” I took a long drink of beer.
“Her exact words, just the other day when we were lying in bed, were, ‘I wish Jim could have a girl like you. Someone who could really ring his bell. He needs to experience what a really good fuck can do for a person’.”
“Are you serious?”
“Yes, I am. I tried to think of anyone I knew who I could fix you up with, but other than your mom I couldn’t think of anyone laid back enough for you to experience that with. All the women I know are kind of uptight and too competitive. They’d eat you up and spit you out, and you wouldn’t enjoy that a bit.”
I laughed and said, “Why not? It sounds better than nothing.”
“No, no, sweetie. You need your first sexual experience to be totally awesome. You need someone who will teach you things. It will probably be a woman older than you, too. I’ve slept with girls your age and, yeah they’re amazingly sexy but they don’t know shit about making love. You need a woman over thirty.”
My cock was throbbing at that point, not only at the thought of this very attractive and sexy woman in bed with girls like I’d dated, but I’d never seriously thought about sleeping with an older woman. It was taboo, something for me to jerk off about, not for real life.
“If I find a woman like that, can I fix you up with her?”
“Yeah! Sounds great.”
At that point, my phone rang again. It was Mom, again.
“I should be home in ten minutes, hon. Is Roxy still there?”
It was awkward to talk to my Mom with a raging hard on, but I had no choice. “Yeah, you want to talk to her?”
“Please.”
I handed her the phone. She stood, turned. I studied her tightly denim-clad ass with its luscious curves. She might be the perfect one to teach me, I thought, as she sauntered toward the bedroom. Did she like guys, or was she a complete lesbian? I didn’t know for sure. From the bedroom, I couldn’t hear what she was saying to my mom, but I kind of hoped it was something about me.
Just as Mom said, she got home shortly. Walked in the door, kissed Roxy on the lips, and set down her purse. Then she kissed me on the cheek. “I’m going to take a quick shower, get dressed, and then we can go out.”
Roxy sat on the sofa again, her legs crossed, foot bobbing up and down and a contented look on her face. “I’m taking her to Gino’s for dinner, then we’re going to lady’s night at Raphael’s.”
“Isn’t that a strip club?” I said.
“Yeah, that’s the one.”
“What happens on lady’s night?”
“They have male strippers.”
I must have looked dumbfounded to her. She said, “What? We like seeing naked guys just like most girls do.”
Thinking back on my life, I’d never known Mom to be romantically involved with a guy, it was only women she’d been with. I simply assumed she was a complete lesbian, not bi. Definitely a lipstick lesbian, of course. She was a very attractive woman. I’d had my share of shameful fantasies about her, but never dreamed she was at all interested in men.
Roxy put her hand on my arm. “Looks like you have a lot to learn about your mom. We’re going to have to fix that.” She patted my arm.
The sound of the shower cut off with a squeak of the controls, and Roxy got up to meet Mom in the bedroom. I heard her say something about helping her pick out what to wear as the door closed. I finished my beer and got up to throw away the bottle.
The bedroom door opened and two stunning women stepped out. “Don’t wait up for us, darling,” Mom said, kissing my cheek.
Roxy kissed my other cheek and said, “Unless you really want to.”
With that tantalizingly mysterious thought, they walked out the door. ***
With Mom and her girlfriend Roxy out for the evening, and my cock straining against my pants, thinking of the potential of maybe being with Roxy one day, I stepped into my room and lay on the bed. Thoughts of Roxy consumed me. She looked about thirty five or so, a few years older than Mom. I thought of her coming into my room later that night and crawling into bed with me, showing me how to make love to a woman. The idea of sliding my cock into that woman’s pussy, a pussy my Mom had probably stroked many times with her tongue, got me hornier than I’d ever been. I longed to kiss Roxy’s lips, the lips my Mom had kissed. What’s my fetish, she’d asked – lesbian sex, obviously. Guys talked about threesomes like they were the ultimate experience. Did that turn me on? Hell yes. Not just that, though. Fucking an older woman. And did I dare explore the other that was presenting itself? As much as Roxy turned me on, was it because of her beauty, her sexiness? Or was it also because she was someone else’s girlfriend? If she slept with me, did that mean she was cheating on my mother?
What if Mom said it was ok? What if Mom didn’t mind sharing her with me, letting her come to my room sometimes?
What if they invited me into their room?
My heart pounded as I stroked my cock. Thinking of Roxy lying in bed, beckoning me to come to her. Thinking of my Mom lying next to her, watching. Roxy throwing the covers aside, me laying down beside her. She kisses my lips, long and hard. Takes my hand in hers, places it on her breasts. I squeeze, feel the softness, touch the nipple, as my Mother watches us.
Then Roxy reaches down and slides her hand into my boxers, touching my cock, grasping it, squeezing it. And I moan. Mom props herself up on one elbow to see better, Roxy turning toward her as her strokes quicken. They kiss each other, the pressure of her hand increasing on my cock.
Roxy lays on her back, Mom taking her breast into her mouth, sucking. Roxy’s eyes beckon me to take the other, now Mom’s face is next to mine and we’re sucking a woman’s breasts together. Roxy moans, running her fingers through our hair.
Mom stops, whispers, “I remember when you used to suck my boobs like that. You were just a baby, you loved my milk.”
Then Mom lies on her back, cups her breast in her hand, and whispers, “Do it again. Suck your mother’s breasts.”
Climbing over Roxy, I nestle between them and gaze at Mom’s breasts. They are beautiful; I’m afraid of them.
“Please, Jimmy. I want it.”
I slowly put my lips closer to Mom’s nipple. Soon I feel the flesh brush my skin. Parting my lips, I take her nipple into my mouth and touch it with my tongue. She arches her back and sucks in a breath. I draw more of her breast into my mouth and suck. And I feel Roxy’s hand on my thigh. Or is the hand hers? It doesn’t matter at this point. But Mom whispers, “Roxy, suck my other boob.”
Mom’s girlfriend climbs over us to the other side of the bed and takes Mom’s other breast into her mouth. I realize the hand on my thigh is Mom’s. I part my legs and a rush of adrenaline surges though me.
I see Roxy’s hand slide between Mom’s legs, and the legs part. The hand on my thigh touches my cock, holds it, squeezes it. A voice whispers, “Do you want me to touch it?”
“Yes,” I tell my mother.
“Say it, then. Say it so we can hear you.”
Roxy pauses, looks toward me.
“Touch it, Mom. I want you to touch my cock.”
“Do you want to put it in me?” She whispers hoarsely
I hesitate. “Do you want me to?”
“Yes. I want you to put it in me. But only if you want to. Do you?”
I still hesitate, but not for long. “Yes, I want to put it in you. I’ve wanted to for a long time.”
“Do it, then. Fuck me. And then fuck Roxy. We’re your lovers.”
I move on top of Mom, my cock brushing against her thigh, nudging the wetness around her pussy. Her hands reach around my waste.
“Kiss me,” she whispers.
As with sucking her breast, I hesitate. The thought of kissing my mother on the lips was both repugnant and exhilarating. The times I’d fantasized about her, we didn’t kiss, it was only raw fucking.
“Kiss her!” Roxy said.
“Kiss me.”
I lower myself down, slowly moving closer, feel my lips begin to caress hers. Soft and tender, Mom’s lips part and I press mine to hers. I drink in the simultaneous sensations of passion, horror, revulsion, and pure lust. Her tongue meets mine, her hand pulls my head toward hers. I feel the length of her body pressing against mine, her breasts, her thighs, her legs wrapping around mine.
Our kiss ends with a wet smack. “Now, fuck me,” she says, her legs parting again.
I maneuver my cock between them, Roxy’s hand guiding it. Mom’s pussy is wet and slick, and my cock seems to glide right in. I thrust it deep, and she arches her back, moaning. Again, the feelings of horror and lust well inside me, but the passion wins out and I soon move in a rhythm that was makes Mom whimper. “Fuck me. Fuck Mommie. Fuck me,” she pleads. Roxy stirrs her own pussy, watching us.
Before long, an orgasm welled up in me that was stronger than any I’d ever felt. I squeezed my cock to control it, prolong it. Cum shot high into the air in multiple spurts, landing on my face, my chest, the sheets. In one final burst, I thought of laying in bed with Mom and Roxy, the ultimate threesome. But in my fantasy I hadn’t yet fucked Roxy.