For several weeks, my seventeen-year-old son, Tommy, and I continued what we’d started. We’d moved to my room and its king-sized bed, his twin bed being much too small, but otherwise little changed. Tommy masturbated often, ejaculating on my sheets or sometimes on me, although never in my face. I masturbated little, but more than not at all. I gave him blowjobs that always ended with me swallowing his spurts and handjobs that usually ended with me sucking his cock. Tommy, for his part, often finger-fucked me to an orgasm, no mean feat for a teenager.
I enjoyed these times together. For Tommy’s part, he did pretty much the same thing every time. He came to my bed naked, totally ready. I suspect he masturbated every night whether we got together or not. He would simply push aside the covers, grab his hard dick and stroke it until he came, which usually took only two minutes or less. He’d sometimes slow down when I masturbated with him.
Of course, I let him play with my boobs and finger-fuck me, like I said. He could kiss my breasts, suck my nipples and generally enjoy himself. The only rule was no fucking. For me, I did use a vibrator a couple of times and thoroughly enjoyed that, but more often than not I used my hands just like Tommy did, except that I sometimes used two hands and Tommy never needed more than one. I’d gone from someone who never masturbated in front of anybody to someone who’d do it often, so long as it was in front of my son.
One day, though, things changed. Tommy was masturbating from a kneeling position between my legs. We were both naked and I slowly stroked my pussy. We’d never fucked, of course, he was my son. I’d thought about us fucking, fantasized about it, masturbated to the video of it in my head, but no intercourse was the spoken rule. I’d been very clear about it. Anything else was possible, his cock inside his mom was not.
“Cum for me, honey,” I said. “I want your cum to splatter my pussy.”
He stroked a little faster. I didn’t. I loved watching him, his hand moving quickly back and forth along his dick, his balls barely moving. His dick was just five and a half inches (we’d measured it) and still kinda thin. His balls were small, but he had two testicles, so I knew he’d probably make a fine father someday. Pre-cum appeared at the end of his cock and he rubbed it into the tip. He arched his back, a sign he was close to cumming.
“Now, Tommy, now! Shoot your cum over your mommy. Give it to me, honey.”
He was a lovely boy, although I guess he’d rather be called manly, which he wasn’t. He was a teenager with a lightly muscled body. His grin would light up the room. He had very little hair on his chest.
“Cum for me!”
And he did. Tommy shot a long squirt that landed on my hand, still rubbing my pussy. His remaining ejaculations messed up the sheet between us, the last two simply dripping down his hand.
“Nice, Tommy. I was thinking… maybe you’d like to eat my pussy?”
“Really?”
“Yes, really. I’d like you to. I’ll tell you how. Start by lying down between my legs, your face even with my pussy, a hand on either thigh.”
Tommy did that, he didn’t even pause to lick my boobs. He couldn’t wait. His tongue immediately began to lick between my labia, sometimes touching my clit a bit too hard.
“A little more slowly, Tommy. Lick my thighs. Kiss me above my pussy.”
He started again. His thigh licks were a little messy, but felt good. When he kissed my mons, it felt neutral, neither good nor bad, and I put my hands on his head. I pushed him gently and felt his tongue touching my clit again.
“Now stick your tongue out as far as it will go. Keep it flat, no curling at the edges. Don’t use any muscles. Like that. Now start at the bottom of my pussy and lick all the way up, very slowly, until I tell you to stop. Yes, yes, stop! Keep your tongue relaxed. Do it again, a little more gently, barely touching me. And move your head up slowly. Exactly like that. Oh, my god, yes, Tommy, so nice!”
He continued to lick my cunt. He learned to spend time with my clit, his tongue still flat. We must have done this for six or seven minutes.
“Now, make a little ‘O’ with your lips and put it over my clit.” He kind of knew where it was now. “And suck me gently. Up just a little bit. OK, fasten your lips a little tighter against my pussy. Suck me, Tommy. Suck my clit.”
I was sort of close to cumming, but just sort of, maybe because I was talking so much. Or thinking too hard. I was relaxed but aroused, fantasizing, when Tommy’s lips left my clit, kissed my tummy, kissed a nipple and suddenly his body was completely above mine and I felt his cock at the entrance to my pussy.
“No!” I said and tried to push him away.
He didn’t say anything, but put his hand on his cock and steered it into me. I was incredibly wet by this time and his dick slid in easily, all the way to his balls. It was instantly pleasurable, gentle pressure from his thin cock, but it was so wrong.
“Tommy, you can’t! I’m your mom! Oh, honey, please.”
He pumped his cock in and out. My god, my son was fucking me, his mother. His cock might be smallish, but it felt good inside me. My cunt hadn’t had a cock in it for almost two years. I thought that maybe he wouldn’t cum inside me, just fuck me and finish outside my pussy.
I watched my son’s face, his eyes closed, his lips in a straight line, but the muscles at the corners hinting at intense concentration. The thought of him spurting into me scared me again, even though I was on birth control. He didn’t know that. I unconsciously spread my legs further apart, allowing him easier and deeper entry.
He fucked me for maybe four more quick strokes and I heard him mutter, “Uh, oh.”
Tommy came inside me. After his first ejaculation, I quit saying no and clenched my cunt muscles. My shoulders slumped, but my hips fucked him back. The whole session couldn’t have taken more than thirty seconds between the time he climbed up and when I felt his cock shrinking after cumming.
I should have been furious, but I felt only warmth in my heart. My clit was forgotten. Tommy looked stricken, as though he’d been unimaginably bad. I kissed him lightly on the lips and perhaps wrongly said, “It’s OK, Tommy.”
He kissed me back. His mouth was closed, but I pressed my tongue between his lips. Tommy’s mouth opened and I felt his teeth with my tongue, then it was tongue on tongue for a long minute, mine on top of his, his on top of mine. I felt his chest against my breasts and his soft cock pushing against my pussy.
He stopped kissing me and said, “I’m sorry, Mommy. I don’t know what got into me. I was licking you and then I was hard and after that, it’s a little hazy, but, well, I’m sorry.” He paused. “You felt amazing, though. Being inside your pussy was the best feeling of my whole life.”
“It’s OK, Son,” I replied, sort of pleased. “It was bound to happen sooner or later, I guess. Now you’ve fucked your mother. You really liked it?” Of course he did.
“Oh, Mommy, it was incredible. I’ve never felt anything like your vagina, your pussy. It was… perfect. Wet and warm and soft and it surrounded me. It smothered my dick. It was pillowy soft. It didn’t feel like apple pie at all.”
I would think about apple pie another time. I kissed him a final time and he slid off my body. He wasn’t exhausted, he was just seventeen, but he sure looked sleepy.
“That’s enough for tonight. Good night, Tommy.”
He slowly got out of my bed and walked back to his room. We still don’t sleep overnight in the same bed.
The following night, I was ready for him. I had the lube out, sitting prominently on the nightstand. He walked in naked, his stiff dick leading the way. He lay on the bed next to me. We were on our sides, facing each other, literally face to face. I reached down and stroked his cock.
“Ready for something a little different?” I asked.
He cocked his head and asked warily, “Like what.”
I squeezed his dick and said, “I want you to fuck me in the ass.”
His mouth actually fell open. After five or ten seconds of staring at me, he said, “I don’t know. That sounds kind of gay.”
I smiled. “It’s not gay if you’re with a woman, Tommy. You’ll see. Besides, if you ask me, there’s really no such thing as gay or straight. Everyone is on a continuum that runs from one side to the other. Maybe there are a few people who are off that continuum altogether, but they’re uncommon. Most everyone is at least a little bit gay or a little bit straight. Some, like me, are quite a bit of each, towards the middle of the continuum. We like men, we like women, we like both at the same time. We’re called bisexual, but everyone, I think, is bisexual, it’s just that many lean fairly strongly to one end of the curve or the other.”
“Um.”
“Anyway, you don’t need to agree with me. Look at it this way. You’ve fucked my mouth and now my cunt, I mean my pussy. You’ve fucked my hand. You’ve cum on my breasts and my tummy and my pussy and my legs and my hands and my arm. I’ve basically got one more hole for you to enjoy. Ready?”
“Well…”
“So, we’ll just work up to that. Starting with kissing.”
I’ll admit that I enjoyed being in charge. I kissed him hard on the lips, put my arms around him and pulled him close. I could feel his straight, stiff cock against my pussy. My hands slid down to his ass and I leaned into him, moving my cunt side to side and back and forth. I didn’t do it long, though, I was afraid he’d cum, although he was so young he could cum a second time fairly quickly, I knew. He’d done it just last night.
I reached down and touched my clit, giving myself a jolt. I rubbed it briefly, then gripped his cock. There wasn’t really any space between our bodies, but my fingers circled his dick and jerked it with soft pulling and pushing. Tommy was plenty hard.
“I like to start by getting my ass massaged,” I said.
I rolled onto my stomach. Tommy awkwardly climbed on top, his knees just below my hips. He began to rub my butt. I’d already done my bit, douching my asshole before Tommy showed up and smoking a tiny bit of weed. Tommy could fuck my butt, but I didn’t want to encourage him to do marijuana.
“Use some lube. Just squirt a little on my butt.”
I couldn’t see him, but I felt the silicone Sliquid suddenly dripping down my ass. He used too much, but whatever. It doesn’t smell at all, really. Tommy put a hand on each cheek and began to rub. At first, his massaging seemed to be aimless, but he quickly settled into a pattern, the two hands moving opposite each other, one clockwise and one counter-clockwise. He would do this two times and then reverse the motions. I expected to feel his cock on me, but I didn’t. After a minute or so, I felt him slap my right butt cheek.
“You can spank me a little harder if you want, Tommy. This is the only time you get to spank mommy.”
He hit me twice more, fairly hard, although not nearly as hard as I’d been hit in the past. I enjoyed being spanked with force up to a point. I felt his fingers between my legs and realized he was getting anxious. I moved my knees so they were under my hips, my ass in the air.
“OK, Son, let’s get you lubed up.”
“Do I have to?”
“Yes, you do. Otherwise, you’ll hurt me some. You might even enjoy getting lubed.”
I could hear him open the Sliquid Silver bottle again. He must have poured some on his hand and rubbed it onto his cock.
“And do my asshole, Tommy. Pour some into it and around it and rub it in for a few seconds. I felt the lube fill my asshole followed by his hands rubbing the area, then wiping themselves off on my ass cheeks or at least trying to. The silicone Sliquid was tough to remove. I wasn’t sure Tommy was really ready for this, but I was eager for him to learn.
I love being fucked in the ass and not just because it’s taboo. It often makes me cum. I’m not entirely sure why I get orgasms this way, but they show up, often much quicker than stimulating my front. Tonight, though, was likely to be more of an introduction for Tommy rather than satisfying sex for me.
“Nicely done, Son,” I said. “Now, put a finger into my asshole. Really slowly. Use a finger that’s been lubed.”
I felt it slide in and while I didn’t gasp, I did suddenly breathe in and hold my breath for a second.
“Hold it there for a bit. OK, move it back and forth a little, then insert two fingers.”
This accomplished, we were ready for the big event.
“Is your dick still lubed up?”
“Yes, mom,” he said, reverting to being a seventeen-year-old with “mom.”
“And hard?”
“Yes!” he said with a touch of sarcasm.
“Fine. Get on your back.”
We jockeyed around so Tommy lay flat on his back and I was in the cowgirl position, my knees almost up to his armpits. I grabbed his dick and stroked it a little to get it totally stiff again. His cock was still totally lubed. I jerked it a little longer.
“Here we go,” I said.
I put the tip of his dick at my asshole and eased down an inch. Tommy’s cock was thin and it went in pretty easily. I slid down his pole until I was sitting on him. Tommy’s cock was entirely inside my ass. I could feel his balls touch my ass. Delightful. This wasn’t my favorite position at all, but it was the easiest to get Tommy started with. I’m much more of a doggy-style ass fucker. But I like it every which way and this was fine.
“Mommy, you’re so tight! Mommy! So good!”
I slid his cock up and down. It pulled out maybe eighty percent of the way, then back in something close to eighty percent. I did it slowly for the first minute, then speeded up. I played with my clit, my fingers moving back and forth. His cock began to move up and down on its own.
“I know it feels good, Tommy, but let me control how fast you fuck me,” I said.
He’d begun to pump his dick quickly and it hurt just a little. He stopped doing anything like I’d asked and I slowed the in-and-out to a slow crawl. It felt heavenly, his cock sliding back and forth. I could feel myself becoming more aroused. I clenched my cunt muscles, which kind of include my ass, and felt him tight inside me. I put my hands on his chest and leaned forward.
“Mommy, I’m going to cum!”
I thought about sliding off and having him jack off to finish, but figured it was my son’s first time and instead, I sat down as far as I could go.
“Yes, honey, cum in mommy’s ass. I’m going to make you cum inside me. Now, Tommy, yes! Fuck my asshole!”
I clenched again and felt his cock expand with each spurt. I loved the pulsing of Tommy’s dick. When he finished, I just sat there for a minute, still rubbing my clit, but not very close to cumming.
I eased myself straight up, feeling his softening dick fall out of my ass. Cum dripped out of my asshole. It would, sadly, leak out of my butt for a little while, but that was a small price to pay. I figured that over time Tommy would last longer and longer and eventually I’d get the anal orgasms I craved. For now, though, I simply masturbated.