You dress him up

Ivan stared at that dress for a while almost to a point where I thought I had put him off. The silence grew uncomfortable for me before I called his name again. He blinked a few times and looked down holding his hands. “Maybe.” He said, though I’m not sure he was talking to me that time. Something was bothering him.

“Ivan?” I approached him holding the dress in my hands and sitting next to him. “Ivan, you okay?” He kept his glance to the ground, breathing softly and lost in his thoughts. What ever was he thinking so hard about? Was it something alluring to the dress? He didn’t seem that bothered when Gabs asked him.

Unless... this was something he and Gabi shared. They’re close friends after all, it would make sense why he did so there with her but not here with me. He was comfortable around her but not so much with me, i overstepped.

“I’m sorry, forget it-forget I mentioned it.” I dropped the dress aside as he blinked and shook his head. “No, it’s not you it’s just... something else.” I held his hand softly and spoke up. “Wanna talk about it?”

To my surprise he shook his head no. That’s a first for me. “Well, I understand I guess. I’m just... yea.” I got up and grabbed the dress, walking back to putting it into the drawer when Ivan stood up and raised his voice. “Wait!” I jumped, alarmed at hearing him shout so suddenly. “Wait I just... bring it back please.”

He blushed softly as he stared at the dress in my arms, something was in his head since the last time he put it on but I could only wish he let me in. Crossing his arms, he stepped back and watching me hold the dress up for him as he quietly stared before looking away. “It does look nice.” He said “Looks mixed on you, though.” I laughed and shook my head. “It’s not for me now, it’s for you. Who knows, maybe we might go to the mall and pick some more outfits for you, with Gabi of course.”

After a minute he closed his eyes and grabbed his shirt, slowly raising his arms and peeling it off him before tossing it to the floor. He looked over at the front door before looking back to me with a nervous glance, I shook my head yes. “It’s fine, I can lock the door if you want?” He nodded. “Please.” I handed him the dress before walking up and locking it, turning around as he took a deep breath, his body physically trembling. I walked up and hugged him from behind, rubbing his chest softly. “It’s alright, we can still back out if you choose. Up to you.”

“T-Thanks.” He smiled back and raised the dress over his head, putting it on. Stepping back to see him, he kept his eyes closed and was hugging himself. He looked so shy and cute that way, it was fun just to see his reaction but you could tell he was undoubtedly nervous about it. Reaching in to grab his waist, he opened his eyes catching my look as my hands motioned him to wiggle his hips, letting me slide his jeans down along with his boxers. Surprisingly he was sporting a boner, must be part of his way to cope haha. He giggled and covered his face when his cock bobbed and slapped softly against my cheek once his boxers slid down, I frowned and backed away. “Sorry haha, I umm... probs should have said something hehe.” “It’s fine.” I said back, asking him to raise his legs one at a time to step into the panties and skirt, the leggings coming in last. They felt so soft and smooth sliding into his legs too, I nearly lost myself in the moment just helping him put them on. The panties weren’t the best fit with him being hard this time, but everything else was just right for him.

Ivan bit his lip, his face now containing an unmistakable red hue that just wouldn’t leave if he wanted it to. I sat back onto the bed watching him spin around and stare at himself in the bathroom mirror before giggling and covering his face. “I look so dumb right now hehe.” “Naw, you look really cute to be honest.” He waved his hand at me. “You’re just saying that to get me in bed with you. I look silly and you know it.”

Laughing to his comment and look, I never disagreed harder. “Please, you look amazing and you know it. I’m not sending compliments to get a reward, i’m just saying the truth. And the truth is, you’re kinda pretty.” He shook his head and covered his face again. “Staahhhhp no im nooooot.” Walking up behind him, my hands slowly rubbed his arms and pulled them off his face as I whispered to his ear. “I promise you, you’re beautiful Ivan.” He stared at the reflection before looking away. “Do I... still look pretty... without it?” I nod my head. “Would you think of me differently if I stayed like this?” I shook my head no. “What if I like this?” He asked nervously, to which he heard me respond, “Then I’m happy you’re happy, you look beautiful either way.”