“Truth or dare?” I asked him.
It was an old question, one we had asked each other many times before. Perhaps there was something in my voice, something that gave me away. He turned away from the TV we were watching together. His eyes met mine and he held my gaze, as if he could tell I had something unusual planned. The truth was I had been thinking about it all evening, planning it carefully.
“Dare.”, said Tom. There seemed to be some excitement in his voice, too.
“Do everything I say for the next thirty minutes.”
He hesitated, for just a moment. Then a smile tugged at the corner of his mouth.
“Deal.”
“Stand over there and close your eyes.” I said.
Slowly he stood up from the sofa, walked to the middle of the floor, and turned to face me. He met my eyes before gently closing his.
I removed my scarf, watching carefully that he kept his eyes closed. I tied the scarf firmly around him like a blindfold.
“Now, strip to your underwear.”
It wasn’t a question. I surprised myself with the firmness in my voice, and it had the desired effect.
“Yes, Vai” he said, playing along. He took off his shirt, sliding it carefully over the blindfold. Then he undid his belt buckle and, after the slightest hesitation, slid his trousers down and pushed them aside with his foot. I saw the bulge in his underwear and grinned: he was turned on, too.
“Start playing with yourself” I commanded. Without speaking he reached into his pants and slowly started. I could tell he was embarrassed and feeling uncomfortable.
I should encourage him, shouldn’t I? “Woo, yeah!” I said, awkwardly, and wished I’d said something else. But Tom let out a small chuckle at my ineptitude and relaxed a little.
I fought the urge to snap a picture with my phone, and just stayed sitting on the sofa.
Parting my legs and reaching into my own panties I traced my fingers around and along the edge, then let them slip inside of me. “God I’m so wet” I said out loud without thinking, and clasped my hand over my mouth. But he smiled and his shoulders relaxed some more.
Now we were both breathing more heavily and playing faster. Before long he seemed close to finishing.
I stopped, stood up, and stepped closer. Now standing in front of him, I touched my fingers to his lips. His lips parted, welcoming them inside his mouth. If he could tell what I had been doing he didn’t show it, but he sucked them clean.
“Stop playing.” I said. “I dare you to take off your underwear.”
I knew if I started with this he would be reluctant. But now perhaps he would dare to let me see him naked for the first time.
“I hope you aren’t filming this” he said as he pulled off his underwear. I didn’t answer. Instead I took in the sight, and marvelled at this man who trusted me so.
I said to him “Play until you are on the edge of finishing. When you can’t take any more, reach out and put your hands on my shoulders”.
“Vai, you are such a tease!” he said. “I’m definitely finishing myself off later” And he started again. As his breathing became heavier I watched, wondering what it is like to see a boy finish, wondering what it is like to be seen finishing. He was really doing this. I was really watching him. I couldn’t believe it.
Suddenly he stopped and reached out. His trembling, sightless hands brushed my breast before firmly grabbing hold of my shoulders.
He stood there, breathless and naked in front of me, on the edge but helpless to finish.
I reached out my hand and took hold of his length gently. I heard a quick intake of breath from his mouth and he tightened his grip on my shoulders in surprise before relaxing a little. Very slowly I started to move my hand up and down.
“Oh, oh my god… I’m going to…” he gasped.
“Let it happen.” I whispered in his ear, keeping the same, slow, pace.
He opened his mouth as if to speak, but all that came out was quick, deep breaths. His face looked as if he was concentrating intently. He let out a moan as his whole body tensed and then shook as wave after wave shot out onto my hand and onto my dress. He gripped my shoulders as if he would otherwise fall. I carried on rubbing for several long moments until nothing more was left. The mess on my hand was so warm. I took my hand and spread it across his chest, and then his tummy. Idly I wondered what it tasted like.
I kissed him on the corner of the mouth, eliciting a smile. Then I put my arms around my dear friend and hugged him close. He returned my embrace. I took off his blindfold and our eyes met again. He stood there naked, and embarrassed, and out of breath, but comfortable. His eyes shifted on to my hair which he had never seen before, then down to the mess on my dress, then back to my eyes.
“Truth or dare?” He said.
Source: reddit.com/r/eroticliterature/comments/ytfoih/tom_and_vai_part_1_mf_20sdaremild_ds