Sharing My Girlfriend and Her Mom

"It looks good," she said. "If you don't mind, I'm going to take a nap in the living room." She saw my expression and grinned, adding, "with my shirt on this time."

"Do you usually take a nap topless?" I asked casually. I figured that after yesterday, we could talk about it like adults.

"Usually, unless I have my neighbor over to paint," she added. "To be honest, I don't like to wear a lot of clothing. Amy hates it, but I'm not usually out here when she's home." She paused, touching an area of dried paint before asking "speaking of which, did you really rush past without looking yesterday? Be honest, I won't get mad."

"Um, well, to tell the truth, I may have taken a quick look. But I wasn't trying to be creepy, and I did announce myself twice first."

"I'm not upset. It's normal, male curiosity. So then let me ask you another question that you can feel free to answer honestly. What did you think?"

"Think?" I asked, a little slow to pick up what she meant.

"About my breasts," she said slowly, to make sure I understood. "I'd like your opinion of them."

I paused, and she looked at me expectantly, adding, "your honest appraisal. I'm thirty-eight, I can handle it." Her eyes twinkled like Amy's.

"I don't know," I said. "My memory's fuzzy."

I meant it as a joke, and for a fraction of a second she did nothing, and I was terrified I had offended her. I was about to apologize for my comment when the unexpected happened. Without a word she reached up and tugged her tank top down. It had spaghetti straps and came right down and bunched up on her waist. There, not two feet away from me, were her breasts. I stared and she stared right back at me, waiting.

"There you go, to jog your memory," she said casually, her hands on her hips. I said nothing for a moment, keenly aware that I had to say something.

"Um," I said, buying myself a few seconds. "Whoa."

"Can you be a little more articulate, or should I pull my shirt back on to give you some time?"

"No, wait," I blurted out, causing her to laugh. "Okay, okay. Um, they're amazing. Definitely amazing?"

"The nicest you've seen?" she prompted.

"The only ones I've seen. At least not on the internet. But, yes, the nicest I've seen, real or online."

She smiled. I kept expecting her to pull her up top but she didn't. "Well now that you've seen them, I don't really care if you see them again. Would you like that, for me to go around here topless when Amy's not around?"

I nodded feebly, completely entranced by her breasts, and her offer. Was she serious? How could I possibly paint with those things on display?

As if reading my mind, she said, "I'm going to run upstairs and let you finish up." She then walked down the hall and out of sight. My penis throbbed painfully from all of the stimulation that day, but I managed to finish my work and pack up my things. As I was about to leave Susan came back downstairs, her tank top still pulled down.

"Have fun tonight," she said with a grin. I was about to say goodbye when she took me by the hand and gave me a peck on the cheek. "Thanks for making my day," she said. As I headed out the door, she pulled her top back up, adjusting it as if nothing had happened.

I had just enough time to shower and get dressed before I needed to pick up Amy. I had contemplated jerking off in the shower to relieve the tension but knew I'd be pushing it, time-wise. At a young age I figure out how to cum more than once, and I was too greedy to do it just once. Better to wait and fully enjoy it, I thought.

Amy was walking across my lawn when I exited the house.

"I thought I'd meet you halfway," she said. She had the same shorts and t-shirt on, and my mind immediately returned to the memory of seeing up those shorts earlier. Had she put anything on underneath? She kept glancing over her shoulder toward her house as we walked to my car.

"Everything okay?" I asked.

"Oh, yeah," she said distractedly. "My mom won't let up about me going to the movies with you."

"I thought she was okay with it," I said, a little nervous. I felt a little strange going to the movies with Amy after critiquing her mother's breasts an hour earlier.

"She is. She's just pestering me," Amy explained. "It's not you she has a problem with, it's me. She's just so, so nosy," she finished.

We had picked an adventure movie about the end of the world and sat in the very back. The ads were still cycling before the previews, and Amy turned to face me.

"Okay, Henry, I need you to be honest with me."

I panicked inside, worried she knew about her mother, but she added "is this a date?"

I ran through the possible answers but decided on the truth. "I think I'd like it to be."

"Good," she said simply, and raised the armrest between us, scooting closer to me so our thighs were touching. "Because I was worried you were only interested in me as a neighbor. In fact, I was hoping your feelings were a lot more than neighborly."

I couldn't believe my ears, and then she took one more step and shocked me further. She kissed me on the lips, softly. But when I kissed her back her tongue darted into my mouth and before I knew if the movie was already in full swing. We paused, looking at each other. The theater was half-empty and no one was around us.

"I'm not that interested in the movie anyway," she said, and we started kissing again. My hand found her knee, and she put her hand on mine and slid it halfway up her thigh. We continued to kiss and I slowly, slowly made my way closer to her running shorts, hoping that she had not bothered to change at all since I last saw her. She made soft panting noises whenever our lips broke apart. As my hand traveled further up her thigh I wondered how close I could get. I felt the first contact with the fabric of her shorts and realized I was an inch way from her pussy. She kissed me harder, and bucked her hips forward, and my fingers made contact with her soft pubic hair.

She was soaking wet.

Whatever sequence of events led me to that moment, one thing was perfectly clear to me. Amy was very horny and was more than happy to let me have access to her. As my right hand gently brushed her wet labia my left went behind her back and pulled her close to me. I held her tightly as I continued to stroke her labia, marveling at how slippery she was down there. She panted and kissed me as my fingers gently stroked her labia, traveling slightly north and rubbing her tiny clit. She responded instantly, spreading her legs wider and jutting her hips out. I rubbed her clit slowly, putting firm pressure on it as I made tiny circles on and around it. I had no idea what I was doing. This was by far the most experience I had ever had with a girl, but I took my cues from what made her breathe harder, and the rest seemed to come by instinct. No one else was on our row or in front of us, but the thought that we could be caught any second seemed to heighten the fun for both of us.

"Don't stop," she whispered, "I'm close."

I kept the rhythm and pressure the same, and she kissed me harder, her whole body tensing up. I could feel her back muscles tense her her legs spread wider as she started to buck her hips. Amy was coming.

She squirmed and gasped and thrashed against me but I knew better than to stop or changing anything. I kept rubbing her pussy until she slumped against me. My hand was soaked and I could feel the heat radiating from her.

"Where did you learn to do that?" she asked.

"Right here, just now," I said in a whisper.

"Can you do it again?" she asked.

I answered by resuming rubbing her. This time she threw her right leg over my thighs and I moved my left hand lower and gripped her ass. I had dreamed about her ass for years and here I was, cupping it as I rubbed her out on our first date. It took her much less time to come this time, and I kept rubbing her until she came a third time. She was slumped back in the seat, her eyes glassy and her legs spread wide. The credits started to roll and she sat up, kissing me deeply.

"I don't have time to pay you back," she said sheepishly. "I guess I got a little greedy."

"It's okay," I said, and meant it. "Next time."

"You're on," she said, kissing me.

We had milkshakes at an all night diner, just talking about things. Our hobbies, interests. We had a lot in common, including a complete lack of physical experience.

"Can I tell you something totally embarrassing," she asked. "That was my first kiss. And, well, my first time doing that."

"Me too," I said, blushing.

"I can't imagine what you think of me," she said. "That was pretty forward."

"Um, I think you can imaging what I think," I said with a grin. She laughed, and leaned over to kiss me.

"I think I'm going to enjoy this," she said, kissing me again.

I dropped her off an hour later and headed straight up to my room. I had already kissed her on her front door, our bodies pressed together. I had to leave or else I would have ended up rubbing her off on her doorstep. My parents were already asleep and I couldn't wait any longer to relieve the pressure in my penis. After seeing Amy's pussy that morning, and her mom's breasts, and then rubbing Amy out while we kissed at the movies, I was about to explode. I lay on my bed, both hands stroking my engorged penis as I thought about the feeling of Amy's wet pussy, her firm ass, her lips on mine.

As I stroked myself another vision came to mind, competing with my focus on Amy. It was Susan. Topless, her breasts swaying while she walked. How unlike her daughter and yet how they both preoccupied by thoughts. Images of the two darted in and out of focus until I came, spurting jets of cum up my t-shirt. I kept stroking through that orgasm, once again staying hard as I kept at it, thinking of Amy and Susan until I came again. With each successive orgasm less semen issued forth from my penis, but the sensations of each orgasm intensified. Finally, spent after three climaxes, I drifted off to sleep, my penis flopped against my leg, my shirt streaked with my cum.

Life was definitely getting more interesting.

Chapter 3

I got a text from Amy the next morning. She was going to meet me for lunch, but she had some shopping to do first. I headed over to her house anyway, as I had work to do. It was a little strange walking into my girlfriend's house. It was a little strange to call Amy my girlfriend, but she had introduced me to a friend of hers as her boyfriend at the diner the night before. When I walked in I half expected to find Susan topless, and I was right. There she was, napping on the couch. I knew she didn't work; whatever had happened to Mr. Shannon years ago ended up in a major accidental death lawsuit; the Shannons were set for life. It was small consolation for the loss of her husband, but Susan lived a comfortable life.

She was racked out on the couch, a magazine on her lap. Her breasts spilled onto the couch as she slept on her side. She wore a pleated skirt that was, to my surprise, riding up her thighs. Her bare ass was on display. It wasn't as tight and round as Amy's, but it was very nice. A few blonde pubic hairs and just a hint of her labia stuck out between her thighs. I watched, mesmerized, taking in the sight of her almost naked body, when she suddenly stretched, waking up.

"Oh, Henry," she said, as if she'd been expecting me. She looked at me and then looked herself over, realizing her ass was completely exposed. "Well, that's what I get for sleeping in a skirt," she added.

"I didn't mean to look," I said.

"Oh, you don't have to cover," she said. "It's natural. I guess you've seen a lot of your girlfriend's mom the last few days. She told me this morning," she added. "I'm happy for you two. Although," she said, sitting up and straightening her skirt, "I might be a little envious. After all, you are a handsome young man. But how could I compete for your attention? But I guess I probably have it now."

She then stood up, smoothing out her skirt and going about her business without a shirt on at all. It was definitely having its effect on me, and I found myself constantly fighting an erection in my shorts while I painted. She put a shirt on shortly before Amy came home. Amy gave me a hug and a kiss, and I felt guilty that I had been talking to her half-naked mother all morning. My sense of morality was all over the map, and I was wondering how I could be okay with all of this.

Lunch was tense. I felt guilt over having seen Amy's mom topless. And I felt a strange tension between mother and daughter. Some kind of competitive coldness between them. It was perhaps the most awkward hour of my life, although I had no idea how insignificant those feelings of awkwardness would seem later.

Amy then had to go to trumpet lessons and left, leaving me alone with Susan.

Susan's shirt was off before Amy's car had left the driveway. "There," she said, "much more comfortable." She paused, "unless you feel guilty about Amy?"

Just hearing Amy's name made me feel guilty. She could read it on my face, because she added, "Oh, don't be. It's nothing more than nudity. In some cultures, I could just step outside and swim in the nude. It doesn't mean anything beyond that." Susan then unfastened the button on her skirt and let it fall to the ground. Like Amy she had a neatly-trimmed patch of blonde pubic hair, a perfect triangle. I stood there, stunned.

"You should keep painting," she said, as if nothing happened. I resumed my work while she walked around the house naked. My work suffered, as I had to retouch several areas where I had missed because she walked by. A few hours later she brought me an iced tea, and leaned on the wall where I had yet to start painting.

"This is certainly liberating for me, but I bet not so much for you," she said. "You must be hard as a rock."

I blinked in shock, but she just laughed it off. "I know how it works, you know. I can tell your body is definitely noticing. It's flattering, so don't worry about it. No one has seen me naked in over a decade. I have to say I'm enjoying it."

I said nothing, just drank my iced tea while she talked. It helped hide my nerves.

"In fact, I haven't been with a man in just as long," she said, taking a step toward me. Suddenly she took the drink from my hand and set it on the stepladder. I took a step back but she kept on me. She put her hands on my shoulders and gently led me backward to the living room. I was paralyzed with fear, or excitement, or both.

"I would give just about anything to get fucked right now," she whispered, and pressed herself against me. Her hands cupped my ass and she pressed her breasts hard against my chest. She reached up to kiss me and I tried to move back but she was plastered to me.

"Henry," she said with a whisper, "Amy doesn't need to know. I see how you look at me, don't tell me you don't want to."

"I...I don't," I said, trying to find the words. I knew that my resolve was ebbing by the second. If I hesitated any longer I'd give in. But she wouldn't relent, so what could I do?

I decided the best thing to do was to try and head her off. I took her by the shoulders and spun her around. She grinned as I gently shoved her over the edge of the couch. Her chest lay on the couch, with her ass sticking up in the air. I could see her pussy was wet and swollen, waiting for me.

"Fuck me," she panted, her face half-buried in the couch.

I wanted to. But I couldn't. I couldn't do that to Amy. Even if she never found out. While I lusted for her and her mother, my feelings were for Amy only. So I decided then and there to help Susan Shannon as best as I could. I started rubbing her clit, her pussy already soaking wet. She responded, sticking her ass higher in the air. From behind I gently slid two fingers into her warm pussy. It was wet, warm, and smooth, like nothing I had ever felt. I slowly slid my fingers in and out of her as I vigorously rubbed her clit. She panted, bucking her hips to match my rhythm.

I was fingering my girlfriend's mom.

Susan moaned and panted and I felt her pussy contract as she came. I sped up the motion of both hands, my fingers making sloshing noises in and across her wet pussy. I kept at it until she started to come again right on the tail of her first orgasm. I kept rubbing and fingering her, eventually slipping a third finger inside her. A trail of wet fluid ran down her thigh, and I could feel her vagina clamp hard against my fingers with each orgasm.

"Don't stop!" she exclaimed as she came again. She was panting, her whole body shaking as she climaxed. I kept at it through a fourth orgasm, after which she pulled away. Her pussy was wide and swollen, dripping with her juices as she lay forward on the couch. There was a large wet spot on the leather of the couch where she had ground against it. I marveled at my handiwork; apparently both Shannon women liked getting rubbed off. She rolled over, panting, her legs spread and her face flush.

"Whoa," was all she said for a moment, then she added after a deep breath, "any chance I can get you to fuck me right now?"

"I can't, really I can't. I already shouldn't have done what I did," I said in pleading voice that meant 'don't ask me again because I'm at the end of my resolve.' She nodded, gently running her hands across her body.

"Well, any chance I can get you to do that again?" she asked. I opened my mouth to say something but she stopped me. "You better head home. If you stay any longer I'll start begging you. I think if you can just do what you did when I need it, then I can behave myself." She grinned, and stood up and pecked me on the cheek.

"Amy is a lucky girl," she said, as I walked out the door.

I sat in my room, terrified. I had definitely done something very wrong, and yet very exciting. But my feelings of guilt won out over the excitement. It seemed I'd be spending my summer painting Susan's house and finger-fucking her. The memory of her nude body shuddering through climax after climax had my dick throbbing. I was too preoccupied to eat dinner, and I realized it was suddenly dark when I heard a tap on my window.

Startled, I headed to the balcony. My room had a balcony that faced Amy's room. Between us was a massive oak tree. There, leaning over her balcony, was Amy, a few small twigs in her hand.

"Hey," she whispered. "I thought you'd be here when I got home. What's up?"

"Just hanging out," I said nonchalantly.

"Can I come over?" she asked.

I nodded, and expected her to disappear and head downstairs. I looked at the clock and realized it was midnight. I didn't know if my parents, who were happy to hear that Amy and I were dating, would be too happy to have her ring the doorbell.

Instead of heading downstairs she suddenly climbed out of her window and onto a thick branch of the tree. I looked alarmed but she just grinned. She deftly crossed two more branches and then dropped quietly onto my balcony.

"Well, that was convenient," she said with a grin as she slipped into my bedroom. "I haven't seen your room in a long time," she whispered.

"I know," I whispered back. My parents were asleep down the hall, as was my younger brother.

"So tomorrow my mom wants to have you over for dinner," she said. I couldn't read her expression but I was nervous I'd give something away at the mention of her mom's name. I suddenly felt incredibly guilty for what I had done.

"Amy," I said, but she put a finger to my lips. I wasn't sure what I was going to say, but I had to say something. "Listen, Amy, I need to tell you something."

"Me first," she said. She had a seriousness in her eyes that I had never seen before. "I've been thinking a lot about last night, what happened. I didn't think things would go that far. I'm not like that, you know? It's like I said, I've never so much as kissed someone. And I had never had those kinds of urges before. I don't know, something kind of, kind of unlocked inside me."