My Anal Confession on Our Second Date

What I’m about to tell you happened on our second date. The first had already been a frenzy of skin, steamy messages, and that kind of connection you can’t force—it simply appears. After several days of writing to each other nonstop, we met again at her apartment one cold afternoon, the kind when the air makes you want to crawl under a duvet and not come out for hours.

I’ll call her Mara. She was a full-bodied woman, with large breasts, wide hips, and a quiet confidence that disarmed me. She had soft, fleshy hands, and the way she touched my face while she talked was already making me hard before I had even kissed her.

When she opened the door, she smiled as if she knew exactly what she was going to do to me. She was wearing comfortable clothes, her hair loose, and that gleam in the eyes of someone who had been fantasizing about the same thing you had. She kissed me without hurrying the moment I stepped inside, closed the door with her foot, and made it clear that there was no room for shyness that afternoon.

“I’ve wanted you since you left last time,” she whispered.

“Me too. Too much.”

We went straight to the bedroom. The room was warm, the curtains drawn, and the bed rumpled as if it had already been waiting for us. We lay on our sides, facing each other, brushing against one another at first with that delicious slowness that makes every touch feel like an electric shock.

I love kissing slowly before fucking. With Mara it was even worse, because she answered every kiss with one that was wetter, more open, hungrier. I bit her lip, she slipped me her tongue, and she gripped the back of my neck firmly, as if she wanted to bury me completely in her mouth.

My hands began at her waist and slowly moved upward. I felt the softness of her skin beneath the fabric, the heat of her body, her breathing growing deeper. When I grabbed one breast over her shirt, she let out a short moan that pierced straight through my stomach.

“Don’t tease me like that if you’re not going to follow through,” she said, half laughing, half panting.

“I’m going to follow through. A lot.”

I took off her shirt and found those full, heavy breasts, their nipples already hard. I leaned over her and ran my tongue around one, not touching it completely at first. Her back arched on its own. Then I closed my lips around it and really sucked, feeling her tense beneath me.

I heard her exhale through her nose as my teeth barely grazed the nipple, then gave way to my tongue again. I alternated between one breast and the other, sucking, licking, biting softly, enjoying the way her hands squeezed my shoulders whenever I got the pressure exactly right.

I moved up along her collarbone and neck. That area drove her crazy—I’d noticed it the first time we met—so I lingered there long enough to watch her come undone. I kissed her beneath the ear, brushed her skin with my breath, and ran the tip of my tongue along the edge of her neck while holding her hand against the pillow.

She trembled in a way that wasn’t faked at all. Her fingers laced with mine and she squeezed hard. Then she moaned softly, restraining herself, as if holding back made it even kinkier. When I bit her neck a little more firmly, she spread her thighs on pure reflex.

“Fuck... there...,” she whispered. “Don’t stop.”

I kept going without mercy, alternating kisses, bites, and caresses along her neck, shoulder, and breast, until I felt her body change all at once. Her legs tensed, her nipples grew even harder, and her breathing broke into two or three quick gasps. She came like that, with barely more than my mouth and hands touching her, shaking beneath me with a surprise that made her laugh afterward.

We held each other for a moment. Not out of modesty, but to savor that first shared tremor. We looked at each other up close, and I saw her flushed face, wet lips, and wide pupils. I was already completely hard, trapped between our bodies.

Her hand slid down my back to my ass and squeezed it without any delicacy. Then she knelt on the bed and yanked down my pants and underwear. My cock sprang free, stiff, and a filthy smile escaped her that I loved.

“Now it’s your turn,” she said.

She leaned over and licked me from base to tip, slowly at first, just to watch me take a deep breath. She held me between her lips while looking up at me from below, knowing perfectly well what she was doing. Then she opened her mouth wider and started sucking for real, taking me in little by little until I reached the back of her throat.

I brushed her hair away from her face and let her do it. Her hand grabbed my balls and held them warmly, squeezing just enough to drive me crazy. Every time she came back up, the tip of her tongue collected the fluid already leaking from me, and whenever she went down again, she left my cock completely drenched in saliva.

“Fuck, you suck so well,” I told her, my voice broken.

She released my cock for just a second to answer.

“Because I like swallowing it when you’re this hard.”

She took me back into her mouth, and this time she started playing dirtier. She sucked hard, loosened her lips, ran her tongue over my frenulum, then drew breath through her nose so she could take me all the way in again. I felt the hot wetness of her mouth, the pressure of her lips, the massage of her tongue, and the pleasant tug in my balls every time she caressed them.

I had to ask her to stop for a moment because I was on the verge of coming too soon. She pulled away with strings of saliva hanging from my cock, licked her lips shamelessly, and pushed me toward the bed with a smile of absolute wickedness.

“Then make me come.”

I lay beside her, kissed her again, and lowered my hand between her thighs. She was soaked. I slipped my fingers beneath her underwear and slowly ran them over her pussy, up and down, feeling the thick wetness that had already soaked everything.

“Look at you,” I said, showing her my shining fingers.

“Your fault. And mine. Now take this off.”

I slowly pulled her underwear down her legs and opened her thighs. Her pussy was swollen, wet, shining. I began by stroking her clitoris in slow circles, barely brushing it, just to watch her writhe with frustration. Every time I was about to apply real pressure, I pulled away slightly and made her moan with irritation.

“Don’t be an asshole.”

“I haven’t even started yet.”

I picked up the toy from her bedside table, one of those suction toys she liked so much, and turned it on beside her clitoris. The moment the nozzle touched the right spot, she let out such a deep moan that it gave me goosebumps. She closed her legs instinctively, but I made her open them again, holding her thigh.

I passed the device over her clitoris, left it fixed there for a second, then moved it in small circles. Meanwhile, my other hand massaged her stomach and moved down to the insides of her thighs to keep her open. Her body began to tremble in increasingly obvious waves.

“Fuck... fuck... like that... like that...,” she repeated.

She loved the mixture of intensity and control. Whenever I saw her on the verge of breaking, I eased off just a little, then went right back over her clitoris. Her hips rose from the bed, seeking more; her breathing had become one continuous pant, and her breasts rose and fell as if she were running.

She came trembling, clamping her legs tightly around my arm. Even so, I didn’t switch off the toy immediately. I kept it there a little longer, just enough to extend the spasms until she looked at me with glazed eyes and laughed somewhere between complaint and pleasure.

“You’re going to kill me.”

“No. I’m going to leave you empty and begging for more.”

I turned off the toy and positioned myself between her legs. I kissed her mound, then her lips, and breathed in the strong, hot smell of her arousal. She grabbed my hair before I had even stuck out my tongue, eager, open, offering herself completely.

“Eat my pussy,” she ordered in my ear.

She didn’t need to repeat herself. The first lick was long, from underneath all the way up to her clitoris, dragging along all her wetness. She had that thick, salty taste that gets better once a woman has already come. I did it again, more slowly, pressing my tongue down, parting her lips with my fingers so I could get properly inside her.

Mara reacted instantly. Her thighs rose onto my shoulders and she trapped my head between them. I started eating her pussy with no elegance whatsoever, just the way I like it: firm tongue, lips sucking her clitoris, brief pauses to slide in two fingers and pull them out dripping wet. Every time I pushed my fingers in, curling them slightly inside her, she squeezed me with short spasms.

“Yes... yes... keep going... don’t stop now.”

I licked her eagerly, leaving my face wet. I went up to suck her clitoris, then went back down to lick her completely. I slipped in one finger, then two, and moved them inside her pussy with a wet rhythm while my tongue never stopped punishing her clitoris.

When I felt she was close, I lightly nibbled that sensitive spot I knew unraveled her. Mara let out a muffled cry, pulled my hair so hard it hurt, and started coming again in my mouth. It wasn’t one brief release; it was several contractions in a row, accompanied by jets of wetness that left me swallowing and licking without stopping.

I continued a little longer, savoring the way she came and the way she trembled afterward. Her vulva was completely wet, swollen, and sensitive, and even so she kept asking for more with her hips. When I finally lifted my head, her cheeks were flushed and her breathing was in pieces.

We stayed on our sides, tangled together, catching our breath. I wrapped myself around her from behind and began kissing her back and shoulders while one hand caressed her breast. I could feel her ass pressed against my pelvis and my cock, hard again, wedged between her buttocks.

I slid my hand over her belly to her pussy and played with her wetness for a while, just rubbing her entrance and clitoris with two fingers. Then I placed the tip of my cock between her lips and began rubbing her from bottom to top without entering, letting the glans coat itself in her fluid and bump against her clitoris again and again.

She tipped her head back, resting it on my shoulder.

“If you keep doing that, I’m going to start begging you for things again.”

“What things?”

There was a brief silence. I felt her breathing stop for a second before she spoke.

“I want you to do it up my ass. But carefully. I want my first time with you.”

The sentence made me even harder. Not because of the novelty itself, but because of the trust with which she asked me. I kissed behind her ear and stroked her hip while thinking about doing it right, without hurrying, enjoying every step.

“Slowly, then. You tell me everything.”

“Yes. Don’t let go of me. And talk to me.”

I kept her in a spooning position. It was comfortable and intimate, and it allowed her to relax. With one hand I continued stroking her pussy to keep her wet and aroused; with the other I moved down between her buttocks and traced the edge of her anus with the tip of a well-lubricated finger.

I felt her tense slightly at first, then relax when she realized I wasn’t going to force anything. I made small circles around it, massaging, brushing, inserting only the tip of my finger and pulling it out again. At the same time I kept rubbing her clitoris very slowly, so she would associate this new sensation with pleasure rather than fear.

“That... that’s good,” she whispered. “Keep going.”

I kissed the nape of her neck and spoke into her ear.

“I’m going to put in one finger. Breathe. If anything really hurts, tell me.”

I entered slowly. Her anus clenched around me immediately, hot and tight, but it didn’t close completely. I waited a few seconds inside without moving, feeling it gradually give around my finger while I stroked her pussy from the front.

Mara let out a strange moan, a mixture of surprise and arousal. Then I began moving my finger slowly, pulling it out a little and pushing it in again, massaging inside with patience. Her ass gradually opened wider, and her breathing began to speed up again.

“I like it... fuck, I really like it,” she said, almost incredulously.

I inserted a second finger when I felt she was ready. This time she opened her mouth wider as she moaned and squeezed my wrist. I wasn’t in a hurry. I kept them inside, barely separated, stimulating her with short movements while rubbing her clitoris with my thumb. The combination undid her.

She came again like that, with two fingers in her ass and her pussy streaming over my hand. Her legs drew up, her ass squeezed me hard, and I took advantage of that moment to keep opening her calmly, noticing how her arousal made it easier and easier to move in.

“Don’t stop, please. Put it in,” she begged in a hoarse voice. “I want to feel your cock there.”

I slowly withdrew my fingers and used that same mixture of lubricant and her own fluid to thoroughly coat the tip of my cock. I placed it at her anal entrance and stayed still for a second, breathing with her. I could feel the heat of her closed ass against my glans and the brutal urge to push, but I held myself back.

“I’m only going to go in a little.”

I pressed slowly. Her sphincter resisted, then yielded just enough to let the tip through. Mara exhaled sharply and gripped my forearm tightly.

“Slowly... like that... don’t stop, but slowly.”

I kissed her shoulder and kept pushing millimeter by millimeter. When the glans had fully entered, I stopped. I could feel her squeezing me everywhere, much tighter than her pussy, and that pressure was already driving me crazy. She moved her hips slightly, curious, adjusting to the feeling.

“The tip is inside,” I told her.

“Put it in deeper. I want the full sensation.”

I pushed a little farther. Then a little more. Each advance was accompanied by one of her gasps and a pause so her body could accept more. Until finally, with one last slow push, I was completely inside her. We both stayed motionless for a moment, feeling the weight of it.

Mara bit the pillow, then let out a nervous laugh.

“Fuck... I feel you all the way. Don’t move... wait... yes... okay... now.”

When she gave me permission, I began fucking her ass with short movements. I pulled out only a few inches and went back in, keeping a gentle rhythm and giving her time to adjust to every thrust. My hand remained on her pussy, stroking her clitoris so the pleasure never faded.

Very soon she stopped tensing. Her ass began to take me more easily, opening with every thrust and closing around me whenever I pulled out. The sounds changed too: they were no longer cautious gasps, but dirtier, needier moans. She herself began pushing her ass backward, looking for more depth.

“That’s it... fuck me like that... feels so good... fuck...”

I obeyed. I increased the pace a little. I went in and out more decisively, listening to the wet slap of my pelvis against her buttocks and feeling her milk me with every movement. The kink of being inside her ass for the first time, hearing her ask me for more, feeling her pussy soaked while I masturbated her from the front, was taking me to the edge.

“I want to feel you harder,” she said. “Pull it out and take me doggy-style.”

I withdrew slowly. She moaned at the empty feeling and got onto her knees on the bed, propped up on her forearms. From behind she looked beautiful: her back arched, her big white ass spread open for me, her hair falling to one side of her face as she glanced at us in the wardrobe mirror.

I stroked her buttocks, spread them with both hands, and spat a little more lubricant onto her anus before rubbing the tip of my cock against her entrance again. The simple gesture made her shudder.

“Put it in,” she said, looking at herself in the mirror. “I want to watch you fuck my ass.”

I put it back in slowly, but without stopping as much as before. This time her body already knew what was coming, and she let me enter almost to the base with a long, muffled moan. When I was pressed completely against her buttocks, she went still for a second, staring at her reflection with her mouth open.

I began thrusting into her for real. At first I set a steady, deep, controlled rhythm. Then I went a little harder. My cock entered her ass wet, tight, hot, and every withdrawal invited me back in with greater hunger. She moaned with every blow, moving her hips backward to take me better.

I brought one hand to her pussy and began rubbing her clitoris while I fucked her from behind. The combination destroyed her. In the mirror I could see her flushed face, disheveled hair, parted lips, and breasts swaying with every thrust. I could see myself behind her too, sweaty and focused, driving my cock into that ass that was already opening and closing to my rhythm.

“Harder,” she begged. “Don’t treat me like I’m made of glass.”

So I did. I grabbed her hip with one hand and her hair with the other, not actually pulling it but holding her firmly, and started fucking her harder. I went all the way in and pulled almost completely out, again and again, until the sound of our bodies filled the room. Her ass took every thrust better than the last, and she answered with open, shameless moans.

“I love it... I love it... don’t stop... I’m going to come again.”

I rubbed her clitoris faster. My pelvis struck her buttocks with an increasingly urgent rhythm, and I was already on the verge, my balls tight and my cock pulsing inside her. Mara came first, squeezing me suddenly as she shouted my name with her face turned toward the mirror. Her orgasm shook her whole body, from her shoulders to her legs.

That contraction finished me. I gave three more deep, disorderly thrusts and came with a growl, clutching her hips, feeling the orgasm empty me inside that hot, tight pressure that wouldn’t stop squeezing me.

We stayed like that for a few seconds, panting and pressed together. Then I slowly pulled out and helped her lie on her side again. Her skin was sweaty, her face shining, and she wore a tired smile of pure satisfaction.

I held her from behind, kissed her shoulder and belly, and she reached for my hand to lace our fingers together. The room was still warm, the mirror fogged, the bed a complete mess. Outside it was still cold, but in there our bodies were still throbbing as if we had just come out of a storm.

“I didn’t know I could like it that much,” she murmured, still not fully able to catch her breath.

“Because we did it the right way.”

“No. Because it was you.”

We laughed softly. I rested my head on her chest and listened to her heart, still racing. She stroked my hair with the same tenderness with which she had welcomed me when I arrived, then spoke into my ear with a confidence that was no longer nervous at all.

“Next time I want to do it again. And not just once.”

I looked up, kissed her slowly, and knew that second date wasn’t going to remain a mere anecdote. It was a confession, yes, but above all it was the beginning of a habit.