The first time together (18+)
My jaw hung open as the woman of my dreams started to strip in front of me. Or brief date had been full of laughter and learning. She was a strong headed, dominant woman who knew what she wanted. And at the end of the date she wanted me.
I’m not really a ‘guy’s guy’ if anything most other dudes would describe me as effeminate. I’d always been skinny and lithe. A lifetime of swimming kept me thin and lightly sculpted with lean muscle. I couldn’t grow facial hair for the life of me, and kept my hair in a shaggy wolf cut. My complexion could be called, ‘milky’. Not things most women I met wanted.
Wendy slowly unbuttoned her shirt, her impressive bust slowly revealed. A lacy bra beneath it see through enough that I could see her nipples hardened beneath it. Her voice was demanding, “I don’t want to be the only one stripping. Take off your clothes.”
I scrambled to strip down in a hurry wanting to follow her demands. My submissive side quivered at being told what to do. I felt myself growing hard as diamonds as I freed myself from my pants. I could feel Wendy’s eyes on me, I could feel the heat of her hunger. Soon I was stripped and bare, sitting on her futon at full attention in two ways.
Her chest was bare before me, her breasts’s size mixing the fight between perkiness and the reality of gravity wanted to pull such an impressive display downwards, “Come here. Touch me, fondle me.” Wendy knew what she wanted, and demanded it.
I was with her in moments. I began to kiss the slope of her breast as my hands cupped and lifted them. Messaging the thick soft flesh. Her hands cupped the back of my head as she pulled me tight against her. I could smell the rose perfume she was wearing flood my nose as I was so close to her. She moaned as I kissed her collarbone and I felt myself twitch. She tasted like honey soaked strawberries as I brushed my lips across her skin. She pushed and guided me down to her nipple and I took it into my mouth sucking and biting on the flesh. I wrapped my arms around her and squeezed her ass. She moaned as her nipple grew hard in my mouth. I ran my tongue around the diamond it became. Memorizing her flavor.
As I pulled her against me I was in for a surprise. I paused and looked down at the impressive bulge beneath her skirt. I was confused but her voice cut through me, “Take off my skirt.” I found my hands almost controlled by her demands as I unzipped the side of her skirt and it dropped away. Trapped in a pair of tight bloomer shorts was something much larger than myself. She leaned forward and painfully bit my ear. “Kneel, take off the shorts.” Her hands gripped my shoulders and insistently pushed me down to my knees.
I didn’t have the strength to fight her as my hands cupped the top of her shorts and pulled them down. A truly impressive cock sprung from them as she gripped the back of my head and rested it on my face. A smile of triumph stretched across her lips. As her balls rested against my chin the head of her cock touched my forehead. The musk of sweat was heady and made my head swim as one finger stroked my lips. Wherever she touched me felt like being kissed by fire.
My voice quavered, “You’re trans?” I couldn’t believe someone so feminine presenting would have such an impressive dick shoved in my face.
“More… hermaphrodite. Reach behind my balls, you’ll feel my tight little slit. I don’t usually let someone touch me there, but be gentle and I won’t punish you.” Her voice seemed to control me like I was Wendy’s puppet as I cupped her heavy balls in one hand and reached up and behind them. There my fingers brushed a moist soft pair of lips that radiated heat and moisture as she shuddered at my soft stroke. “See, both parts. But you get my cock today. Take it.”
I slid me head down, so incredibly turned on as I gazed upon someone that was just like my most watched porn. I pushed out my tongue and slowly dragged it up the underside of her dick. The salty taste of sweat from such an impressive thing trapped in shorts all day. She moaned, “Oooh that feels so good. You like cock don’t you?”
“Yeah baby, and I like to make them feel like heaven wrapped around them,” I touched my tongue pressing against the meat of her cock. Then I wrapped my mouth around her tip and circled the head of her cock with my tongue. It gave just slightly to the pressure and I could feel it throb against me. My lips got so hot with her trapped between my lips. My having been with other men before had taught me how to please someone with my mouth.
“Ohh, that’s it. Be a good little bitch for me and keep at it.” Her fist grabbed my hair as she pressed further into my mouth. Filling it with her girth. My tongue was shoved beneath it and I couldn’t circle her most sensitive head. I tilted my head back to rub it against the top of my mouth. I gently massaged her balls with one hand as the other wrapped around the base of her dick. “Fuck me, your such a good little cock sucker.”
As I pulled back I followed with my hand so it could be slicked by the spit flooding out of my mouth and coating her cock. I moaned around her thickness.
“Oh that makes me feel like I’m so deep in you. Fuck, that feels good.” She groaned and I could see her eyes almost cross at the pleasure I was giving her.
My own dick was so hard it ached, I could feel precum dripping from it and falling in the crack between my thighs. I felt a reverence fill me as I pleasured this dream of a real life futanari before me. I dipped her as deep into my mouth as possible and made sure to breath through my nose to minimize the gagging it wanted to cause. I twisted my hand at the base of her cock to tantalize the nerves there. I could barely wrap my fingers around it as it pulsed with her heartbeat. I pulled her free of my mouth and stroked her with my hand as I bent down to take her balls into my mouth. She whimpered at my parting lips.
Wendy’s balls were thick and heavy as I pulled one into my mouth, she gasped at the feeling as I pumped her. I used my tongue to study the shape of her testicle. I let the one in my mouth free as I twisted my tongue to the other and took it in. I let my teeth scrape against it and she hissed, “Careful,” she demanded. I pulled my teeth back. She ran a finger down my ear sending goosebumps down my body as it tickled pleasantly. I returned to her dick as my spit was starting to be too thin to keep jacking her off.
I kissed the side of her tip as I slowed down my hand, “Do I make you feel good.”
“So fucking good, now give me that mouth again. I’m going to fuck your face.” Her hand gripped me as she shoved the head of her cock against my lips and forced it into my mouth. I moaned to make her feel good as I let it slide deep in me. Both of her hands gripped my head as she took control. The mixing smells of sweat, spit, and perfume flooded my nose as I fought to breath.
“Ahhhh, fuck you feel good,” Wendy pulled back and thrust controlling me as she began to fuck my mouth. I found myself taking desperate breaths through my nose as she pushed against the back of my throat. Begging to throatfuck me. I couldn’t, I’d never done something like that. She groaned above me as I let go of the base of her cock and braced my hands on her hips trying to slow her down. But she was deceptively strong.
“I want you to stroke yourself while you pleasure me. Let me watch you squirm. But don’t you dare cum unless I tell you to.” She pulled herself free enough for me to pump her cock and slick my hand with the ropes of drool that had fallen from my mouth. Wet and ready I wrapped my hand around my cock as she started to fuck my face again. I stroked myself with one hand as the other tried to brace against her hip again. I felt an orgasm come to me so quickly I had to pause my hand wanting to listen to her dominate me. I moaned in absolute submissive pleasure. The feel of her balls slapping against my chin wet as drool seeped from my lips down to coat her.
“Ohhhh fuck I’m gonna cum down that throat of yours. Relax, let me slide into it. Swallow me down baby.” She pressed hard against the back of my throat and I gagged against it. I couldn’t breath with how thick it was. She pulled back as I gasped through my nose, “I said swallow me down little bitch.” Again she thrusted and I relaxed as much as I could. Wendy’s thick cock stretched my throat as she forced herself past where she had been before. It was like taking too big of a drink of water as my body tried to adjust to her. I could feel her body press against my nose as I quietly gagged on her. The feeling of her thin pines tickling my nose “That's it, be my good little cocksleeve. I’m so close.” She pulled back and I tried to pull away, to get air and could barely breathe before she was down my throat again.
Three thrusts down my throat as she cried out, “Ooooh yesss, that’s it. I’m cumming!” I struggled to hold on and I could feel her cock swell inside my mouth as she began to erupt thick ropes of cum straight down my throat pouring her ecstacy into me. I was trapped by her hands as deep as she could go down my throat. She grunted as her body shuddered against me. “Fuuuuuuck! Oh god,” she groaned as she pulled back, freeing me from suffocating on her. As Wendy popped out of my mouth she twitched more, coating my face in more cum.
I was a gasping mess as I tried to recover, I could feel my eyes watering and my nose run lightly. The cum had forced one of my eyes closed as I felt her grow limp against my face. I was coated in spit and cum, it was hot on my face. As I struggled to recover any sense of myself she stroked my hair gently soothing the toiling tide of fear and desire, “You did so good baby. I’m gonna clean you up, then I’ll take care of your needs.” I could feel her shudder in post orgasm bliss as she caressed me.
Wendy knelt slightly above me as I had sagged onto my heels. She started licking her own cum off my face, groaning at the salty taste of herself. I didn’t know what to do besides to catch my breath and moan, “Mmmm yes.” As soon as she was done she wrapped her lips around mine and pushed her tongue into my mouth. Circling my own as she guided me to lay down beneath her. My body ached for its own release as she ran her manicured nails down my chest sending me into spasms of need for more simulation. “You felt so good, it's your turn to feel good. You want that don’t you.”
After I gave the slightest hint of a nod one hand wrapped around my still wet cock as she trailed kisses down my jaw, trailing down my neck. She stroked slowly and steadily. I moaned loudly unlike any time Derrick or Sandra had touched me. “Ohh god.” I felt the well of an orgasm build up but just as I swelled for release she stopped and made me wait. I couldn’t help but whimper as she paused. I tried to thrust into her hand as I whimpered for my release.
Her lips brushed one of my nipples before she nipped at it with her teeth sending a shock of pain through my chest. I wrapped my hands around her back still feeling so weak. Just as my orgasm ebbed away she started stroking again. Keeping me on a delicious edge of my own ecstasy. Her lips trailed down my tummy and into the peach fuzz I had for a happy trail. My eyes crossed and I could feel drool dripping out of the corner of my mouth.
Then her lips wrapped around my cock. I ached for release as she slid me deeper. Moving ever so slowly. I barely reached the back of her mouth as she took me as deep as I could go. She bobbed her head as I gasped, she moaned around me sending me shuddering. I couldn’t help but beg, “Please let me cum. I want it so bad.”
She laughed throatily with me pinned in her lips. One of her hands slid down behind my balls and stroked my asshole, jolts of pleasure rushed through me. She pulled her mouth free, “Have you ever had your prostate milked before baby?”
“No,” I gasped. I had never gotten that far with other men. It was usually just reciprocal blow jobs and hand jobs. My recent explorations had opened my eyes to further stimulation.
Her fingers trailed my cock soaking up spit and slicking her fingers. “Raise your legs up so I can do a good job.” So I listened, she took me back into her mouth as Wendy slipped fingers inside me. I relaxed as she entered me. I could feel her fingers stretch me slightly as she pushed into me. I felt so full from just her slender digits as she began slowly fucking my ass with her fingers.
“Ooooh fuck, that feels so good.” I could feel the drool reach my ears as I clenched trying not to scream out in my bliss. Sure the neighbors had already heard too much.
She curled her fingers pressing up as if reaching for the base of my cock from inside me and I could feel something shoot through me as she found my prostate. “Oh fuck,” I moaned as she wrapped her fingers around the lump of it and stroked it slowly. Like a deep bottomless well of pleasure it lingered there waiting for me to be shoved in. Keeping pressure on it she kept me on that edge. The pleasure rushing through me sent quivers across my whole body as I closed my eyes.
“You can cum now. You have my permission.” She took me in her mouth once more. The bobbing of her head and the massage on my prostate blinded me with my own orgasmic bliss. It was like fireworks exploding in my brain as I throbbed and pulsed shooting the thickest heaviest load of my life as the most powerful orgasm wracked my body. I could feel Wendy swallowing my cum with every pulse. She kept it going while stroking inside me and circling the head of my dick with her tongue. I shuddered and weakly pressed against her trying to free myself from the overwhelming bliss. She tortured me with my own pleasure as I mewled like a kitten desperate for freedom. She didn’t stop as I tried not to scream in pained overstimulated bliss, “hmmnnk!!!”
Then she was pulling me free from her mouth with a pop as she slowly slid her fingers out of me. The slow movement filled me with one final shudder as she knelt between my legs. I was so blissed out I couldn’t move. A feeling of being hollowed out by my own pleasure filled me. All my meager strength sapped away by this futa that dominated me. She crawled up my body and kissed me deeply. I could taste the mixture of her and my cum on her lips and it was divine. I could smell the stink of my sweat on her and I inhaled deeply that some part of me had sullied her perfection. When she pulled back my eyes were closed and mouth open for more.
“Lets go clean up, then we’ll cuddle and you can get the best night of sleep you’ve ever had.” She pulled me to my feet and guided me weakly to her bathroom. Wendy started water as I swayed on my feet, my body swimming from pleasure beyond my imagination. She guided me into her shower and the hot water washed over me. I didn’t know how coated in sweat and cum I had been as she washed me gently. I had no strength as she cleaned every nook and cranny of my body. Exploring me once more as if to memorize every inch. Then she pulled me from the water and stood underneath it. Her eyes looked at me expectantly. “Well, it's your turn to wash me.”
I took the soap into my hands and started to massage it into her back. Slowly methodically reaching down to clean the plump cheeks of her ass. I dared to slide my hand between them and brush against the rose bud of her asshole and she moaned, “Careful, you might get me going again. I don’t think you can handle more tonight.”
I reached around Wendy washing her stomach and slowly up her body as the water rinsed away my work as I did it. I applied more soap and cleaned her breasts and collar. I slid my fingers through her armpits and she giggled. She was ticklish and I put that somewhere in my brain. I rubbed her shoulders and neck with the soap as she groaned at the attention. I knelt behind her and started to wash her legs last, running my hands up them stroking the skin reverently as I tended to her. Then she was clean, she rinsed off and let me warm up in the water before shutting it off. I didn’t know I had gotten cold standing free of it.
Before I knew it we were back in her futon wrapped in blankets as snuggled up on my chest. I could feel her bare skin radiate heat as we cuddled. She kissed my chest as I drifted off. I had never felt so truly taken care of after such an intense session of sex. I fell asleep aching from pleasure. I hoped it wouldn’t be the last time.
Guess I should tell you how we got here.