Our First Time with a Toy

My name is Teo. I'm a 22-year-old trans man, and I have a fuck buddy that I've been seeing for almost two years. His name is Chris. We met nearly two years ago on a website where I was trying to find people to hook up with. Until I met Chris, I didn't know that I could cum from penetration. He showed me that, yes, I most definitely can.

Chris is a 47-year-old gay man in an open marriage with his husband. We tend to see each other only about every 2 weeks because he lives nearly an hour away from me. Every day between those meetings, I'm wishing I could be with him. Thinking about him while I'm at work. Getting wet in my underwear fantasizing about his cock.

Just the other day, I went over to his house. His husband was home; I could hear him watching TV in the living room as Chris came to the front door to let me in and wrap me up in a tight hug.

He asks me how the drive was and gives me a short kiss. He's tall and I'm 5'2" so he leans down and pulls me up onto my toes. Then we head up the stairs to the bedroom. Chat for a minute while we undress. Once I'm naked, I turn to him and he puts his hands all over me, wrapping me in an embrace again. He kisses me on the lips and reaches down to start playing with my pussy, making me moan. I throw my head back and he sucks on my neck. My leg lifts and wraps around him, I'm straining on my toes to make my pussy easier for him to reach, but also to bring my pussy closer to his hard cock. I groan as he grabs my hips, gently pushing them forward and back with his cock lined up against my pussy. The wide ridge of his head feels so amazing as it rubs against my small cock over and over.

He feels that I'm wet and teases me for it, "Already soaking. Did you get excited driving here? Thinking about how I'm gonna please that hot pussy?" I just blush and nod. He lifts me and sets me on the bed on my back, hips lined up with the edge so that he can kneel beside the bed and put his face between my thighs. I'm always so excited for that first feel of his deliciously soft, wet, warm mouth enveloping my cock. He instantly gets me desperate and breathless, panting and moaning as he flicks his tongue on my cock, sucks it into his mouth, and licks my wet slit. He loves the smell of my pussy and occasionally stops to just breathe it in, telling me how hot he thinks it is. That when I'm not here, he jerks off trying to remember the smell and taste of my dripping wet pussy. He knows my body well, and has become so practiced at eating me and sucking me that my body barely needs time to warm up; a few minutes of his mouth on my cock has me so turned on and wet that I'm ready to take his cock.

Chris stands and pulls my hips toward his, lining his cock up with my hole, spitting on his hand and rubbing the head but we already know my pussy is so wet that it'll slide right in. The first push in always stretches me. It's uncomfortable at first and feels so impossibly big. The second stroke is pure fucking bliss. It's what I've been needing all week, it's so good that I already feel like I'm on the edge of cumming. I love when he first starts to fuck me because I can feel how tight my pussy is around his cock. It's so hot; my wet little hole wrapped tight around his hard dick. He climbs onto the bed on his knees and folds my legs up against my chest, lets the weight of his body keep me down on the bed and makes me take his cock. This is my favorite position. I feel totally dominated by him, trapped underneath his large, hairy body, my pussy being pounded into. I wrap my arms around him. I love the feeling when his hairy chest presses against me.

He stops to go down and get a taste of my wetness, then sucks on my cock until I cum for the first time. I cum with his mouth on me and he licks it up as it gushes out of my pussy. He shifts back up to line his cock up with my pussy again and asks, "When was the last time you masturbated?"

I smile and answer honestly, "Earlier today. I was excited thinking about seeing you later."

He smiles back at me and teases me, "Touching yourself thinking about Daddy? Such a naughty, horny boy." Now that I've had my first orgasm, he doesn't hold anything back and begins fucking me hard. Pounding his cock into my pussy deep and rough. He picks a position and fucks me until I cum, then switches to a different position and makes me cum again. It never takes long for me to cum, and sometimes I'm already close as soon as he starts the next position. He fucks me on my back and holds my legs out as wide as they'll go, which gives me a perfect view of his cock plunging in and out of my tight pussy. I cum like that, then he bends my legs in close to my body, putting my feet against his chest. The position gives his cock the perfect angle in my pussy, his wide head mercilessly pounding my g-spot, and I cum hard around his dick. He lets my legs down, then, and lifts his right arm up and lines his hairy, sweaty armpit up with my face. He likes to make me smell him and I love to take in his scent while he fucks me. I take in a deep inhale and can feel my pussy instantly get wetter. He holds me right against him, burying my face in his pit and pounds my pussy while I'm forced to smell him. When I'm close to cumming, he cups a hand over my mouth to stifle my scream. I'm not sure if it's out of courtesy for his husband downstairs or if he just wants to gag me.

When he fucks me through one more orgasm, it's so intense that I have to pull away from him, my body totally overloaded, my pussy sensitive and overstimulated. He just laughs and gives me a break to drink some water. As I'm catching my breath, he reaches over to the nightstand where there are two rolled up washcloths and two folded ones. I had noticed when I walked into the room that there were more than the usual couple of towels he puts out for clean up, but I hadn't thought much of it. But now, he drops one of the rolled up towels next to me on the bed, and smirks at me as I set the water back down. Out of the rolled towel, he pulls a heavy, metal, curved dildo. It's not shaped like a penis, but is curved and has a small ball on one end and a larger ball on the other end. I just look at it and don't know what to expect or what he's planning on doing with it. We've never used toys together before.

I lay back and he gives me a good look at the toy, then lines the larger end up with my pussy and applies pressure until the large ball pops past my tight lips and inside of me. I gasp. He starts moving it around in different directions, just experimenting to see what gets a good reaction out of me. He twists the toy so that it presses against different parts of my pussy, wiggles it around, and finally starts pushing the hard, steel ball against my g-spot. It feels absolutely insane and I'm instantly about to cum. But first, he stops and takes my hand in his, guides it to the end of the toy that's sticking out of me, and tells me to give him a show.

I slowly start to fuck myself with it, feeling the wide ball move against my sensitive insides. He watches me and jerks off, tells me how hot it is seeing me pleasure myself with that hard, metal toy. I start pumping faster, moaning and driving myself crazy, loving how much he loves watching, loving having an audience while I play with myself. He licks one of his thumbs then sneaks it between me and the toy so he can rub my cock while I fuck myself. This pushes me over the edge and I cum around the metal toy, writhing and moaning on the bed in front of him like a desperate little whore. He takes hold of the toy again and really starts to give it to me, finding my g-spot with the end of the toy and twisting the toy to either side, over and over so that my g-spot is massaged by it. I cum at least two times, back to back, screaming and bucking my hips and begging for him to keep going. When I'm not throwing my head back in pleasure, I look down at him and he looks up at me with his eyebrows drawn up, a look of feigned innocence and concern. "That feel good?" He asks, then laughs at me when all I can do to respond is moan and move my hips.

He teases me with the ball end of the toy, pulling it out of my entrance then pushing it back in, pulling it out, pushing it back in, stretching my little pussy lips every time the ball penetrates me. He pulls it out, then turns it around to slide the smaller end inside of me. "Do you think I can fit my cock in next to it?" He smirks at me and has me hold the end of the toy while he lines himself up. I'm nervous about having so much inside of me, but when he finally gets his cock in, the stretch feels amazing. I feel so filled up, stuffed with his cock and the hard toy. He fucks me with his cock while I move the toy as well, until he finally can't hold on any longer and he pulls out and cums all over my stomach and chest, cursing and moaning through his orgasm. He collapses next to me and we smile at each other, in awe of our own sexual chemistry as we always are at the end of a fuck.

Before I can cuddle up to him, he sits up to grab the second rolled up towel from the nightstand and drops it on the bed like he did with the metal toy. I wait for him to pull whatever's inside out, but he just gives me a mischievous grin. "What about this one? Or should we save it for next time?" He looks to me for an answer.

I'm completely fucked out, exhausted, and more than satisfied, but still curious about what fun he could be hiding in that towel. "What is it?"

He just laughs and sets it back on the nightstand, "No, I think I'll surprise you with it next time."