Me and Arin arrived back at my place after he finished changing. He was nervous about the whole double date thing as he was worried that he would be exposed as a cross-dressing pervert if anyone found out. I was sitting at the couch trying to find something to watch when he sat beside me and layed his head on my shoulder as we cuddled up together.
"What if anyone finds out I'm a guy?" he asked nervously as huddled even closer to me
"No one will find out, trust me. You already look like a girl even without a dress and make-up.
"No I don't! I look like a very manly man alright?" He stated as he flexed his arm, revealing a small barely visible cute muscle.
"Sure, manly man." I chuckled as I looked at my phone to see who just texted me.
"Who is it?" Arin asked as he peered at the device
"Todd, he's saying the double date will be on Sunday and that we get to choose the location." I answered as I put my phone away.
"Sunday?? But that's just 2 days from now!" He shouted as he panicked
"Ooo yea, that's not a lot of time to buy you a skirt and a wig." I said while turning off the tv realizing there's nothing good to watch right now
"That means we only have tomorrow to prepare right?" he asked as he hurriedly got up looking all panicked
"Relax, I know a mall nearby where we can probably get everything we need. We can go tomorrow." I said as I took out my phone to google the address
"I'll text you the address, here." I said as I sent the message
"Thanks a lot David." he said, calming down a bit
"No problem." I replied nonchalantly
"Not just for this but for always having my back and listening to my worries too." He said as he approached me and gave me a big hug
"Hey, what are boyfriends for." I replied as I hugged him back
"Anyways, I need to get home and prepare some stuff." he said as he stopped hugging me and tidied up his belongings
"You don't want to stay for dinner first?" I asked a bit disappointed that he won't be staying longer
"No, I need to prepare some stuff for tomorrow and Sunday." he said as he opened the door to the exit.
"Sure" I said with a dejected tone
"Hey, we'll see each other again tomorrow alright?" He reassured, trying to comfort me
"I know, I just hate it whenever you leave." I admitted as I walked to the door and gave him a kiss on the lips
"Well, I hate leaving too but I really need to prepare some things so that everything will go smoothly." he reinforced
"So what time do you want to meet up?" he asked as he was just about to leave
"Let's meet at 9 around the north entrance of the mall. The one by the coffee shop." I answered as he agreed and left after we kissed for one last time.
'I miss him already' I thought as I saw him leave as he got further and further. I only went back inside when I couldn't see him anymore. I layed on the couch and ate some leftover pizza from yesterday and played some video games before deciding to sleep.
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It was hard for me to wake up as I stayed late playing video games. I thought that I had some time left but soon found out that was not the case as I looked at my phone and saw that it was already 9. I quickly panicked as I got up and quickly got dressed and left in a hurry.
It was around 9:20 when I arrived at the mall's entrance and saw Arin sitting there on a bench beside a tree wearing a white shirt, a letterman jacket, and jeans.
"Hey Arin! Sorry I'm late." I huffed as I was tired from running here. I sat beside him and tried to talk to him but he seems to only puff his cheeks and look away from me, continuing to ignore me.
"I'm sorry Arin. Please stop being mad at me. I promise it won't happen again." I pleaded as I hugged him, hoping he will stop being mad
"I can't believe you're late for our first date." He sighed as he finally looked at me
"I... there is no excuse really. I just overslept and I feel really really guilty. Let me make it up to you alright?" I admitted as I held his hand and pulled him up. We're both standing up now holding each other's hands.
"Sure." He said as he finally smiled as we entered the mall. We first tried to find a place where they sold women's clothing. We walked by an adult store which was pretty interesting. We both walked by awkwardly as pretended we didn't see anything knowing we'll probably go in there some day.
We finally arrived at the store we were searching for as we entered. We browsed for a while when I picked up a pair of red lingerie and showed Arin.
"Why don't we buy these? I think they'll look good on you." I teased as I saw him instantly turn red.
"Nononononono. Stop it David. That's too embarrassing." He complained as he smacked the piece of clothing away. I put the lingerie back from when I found it and we continued to search for clothing until we found one that he finally agreed to wear.
"What do you think about this one?" I asked as I picked up a black and white dress.
"Isn't the skirt area too short?" He said as he examined the dress
"Not if you wear stockings and besides I think they'll show off your cute shoulders." I said as I pictured Arin in the dress.
"Fine, I guess I'll wear this one then. It's been too long anyway." He said as it has been a few hourse since we began browsing.
"I'll try it on first to see if it fits. D-don't peak ok?" He told me as he went into the changing room as I stood outside standing guard. It's been a while and I was getting a bit impatient so I went inside the changjng room.
"C'mon I've seen you naked, I think that I ca-" I stopped as I saw Arin in the cute dress. His nakes shoulders visible. He was putting on the stockings, when he suddenly threw his short heels at my chest
"Idiot! I said no peaking!" He shouted all embarrassed as he closed the dressing room curtains
"Are the panties really necessary?" I asked as I blushed. Getting a glimpse of his black lacy panties before I was thrown out
"W-well, I don't want people to see that I'm wearing boxers and find out I'm a guy." He stuttered as I could imagine that he was probably really embarrassed.
After a while he told me that it fit and after he finished changing back, we bought the clothes and was now going to a wig store to find a good wig for Arin. In the end we went for hair extensions as they looked pretty much the same and Arin said that they were more comfortable. We were walking when suddey my stomach rumbled loudly.
"Was that you?" Arin asked, looking back at me
"Yea. I haven't eaten since morning." I said as my stomach grumbled again.
"Jeez, you should've said that earlier. We could've found a place to eat first." He said as he tried to take the shopping bag I was carrying from me
"No. No. I told you that I was going to make it up to you. So I'll be carrying these and you just tell me where you want to eat." I said as I firmly held the bags, not letting him take them.
"Fine. The how about... we eat there..." he said as he pointed at a mcdonalds
"You sure? You don't want to eat somewhere more fancy or expensive?" I asked
"No. No. Besides this is the closest, you won't have to wait long before they serve you food. I can't afford anything too expensive anyway." He said as he instead opted to grab my hand and drag me into the fast-food chain.
We ordered a full meal for each of us which included a burger, coke, and fries and an extra chicken nuggets for us to share.
I paid the cashier as we took our food as we sat down at our table.
"So how much do I owe you?" He asked as he took out his wallet
"Nothing. I'm paying." I replied as I dug into my food
"C'mon let me pay for something at least. You already bought me the clothes and the hair extensions." He said as he tried to hand me money.
"I said nope. Besides, Todd is paying for those. So let me buy you this alright? We're on a date after all." I said
"Fine. Don't treat me like a girl alright. I'm a man too so I'm paying for us next time." He said as he placrd his wallet back as he blushed
"Do you not like the way I treat you?" I asked worriedly
"No it's not that. I like the attention and care you give me but I still have a man's pride you know?" He said as he blushed, also finally starting to eat
"Well, you can repay me later tonight then when we get back home." I flirted as I gave him a sly wink.
"S-sure." He said as he blushed
We finished our lunch and started to scout for a restaurant for the double date. I convinced Arin not to feel bad for Todd as we selected one of the fanciest restaurants at the top floor eith a view of the city. I made a reservation for four and we decided to go home for the day as I was pretty tuckered out.
We finaly arrived back at my place and I set aside the things we just bought on the couch as I layed there as well.
"Hey David, do you think I can stay here for the night?" He asked as he layed there beside me
"Sure, you're always welcome to stay here Arin." I said as I put my arm around him.
"Thanks, because I told my dad already that I'll be staying ay a friend's place. And also, do you have any makeup here?" He asked as he said that last part quietly
"Hmm? Yea I think my mom has some. They should be in the master bedroom." I said as I pointed him in the correct direction
"Thanks, because I think I need to put some on if I want to look convincingly like a girl." He said as he blushed
"Hmm yea sure, do you know how to use it?" I asked as I was confused on if he knows how to apply make up and if he does how does he know
"I have some understanding. I watched a lot of make-up for beginners tutorials yesterday and I should know how to use it." He said as he got up and went to the room where the make-up is located
I fell asleep for a while when I got up and it was already dark outside. I tried to find Arin and remembered that he was in my parent's bedroom. I walked inside and saw him in the dress, stockings, and the short heels he just bought. His face was brighter than before and his lips was pinker due to lipstick.
"D-david... I was just practicing for tomorrow. It's not like I like doing this stuff or that I'm a pervert." He stuttered as I walked up to him and just kissed him
"I think this little guys says otherwise." I said as I grabbed his boner which was showing through his dress.
"S-stop we can't get this dress dirty." He said as he tried to pull away. I instead pushed him down until he was sitting on the floor as I unzipped my pants and whipped out my throbbing member.
"Then, I guess you can't let even a drop leak out." I said as I put my dick in front of his mouth.
"N-no. I- I'm not doing this." he stuttered as I saw that he was barely resisting the urge to put my dick in his mouth
"I'll just wait for your slutty instincts to take over then." I teased as I rubbed my dick on his lips and let him have a good whiff of the stench of my cock.
It wasn't long before he succumbed to his submissive instincts.
"I- I can't take it anymore." He said as he opened his mouth and started sucking my cock.
"You know why I know you'll suck my dick sooner or later even though you just bought that pretty dress of yours?" I asked as he ignored me seeming to be in the trance of sucking up and down my cock
"It's because I know you're daddy's obedient little slutty girl." I said as I softly put my hand on his golden hair
"I-I'm not a girl!" He replied before quickly contiuing to suck my dick.
I then pulled away my dick from him to tease him and pull him up for him to be right in front of the mirror.
"Yea you're not a girl." I said while making him see himself in the mirror.
"Stop it. Just let me suck your dick again." He said, trying to get back down on his knees.
"Admit that you're daddy's little girl first, princess." I teased as he pouted
"I- I'm not going to say something so embarrassing." He retorted as he crossed his slender arms.
"Fine then. I'll just masturbate so that you don't get to suck my dick or swallow my cum, because only a girl would do that. A straight man like you wouldn't possibly want that." I said as I put my throbbing boner back into my pants and zipped the zipper back up.
"F-fine! It's not like I want to suck on your big... juicy... delicious... cock..." he said as he thought about it
"I-I'd rather put my dick inside a hole anyway to get off." He lied as he puffed out his cheeks
"Fine. I'll just sit here and masturbate then." I said as I sat on the bed as I pulled out my dick again and started slowly stroking it.
It's not long before he sat beside me and just watched me stroke. His boner clearly visibly poking his dress.
"Hey David...can we continue what we were doing before?" he muttered
"Beg for it properly." I demanded as I continued masturbating
"I- I'm sorry daddy. I'm your slutty little girl who can't live without your big massive manly cock. Can I suck it. Please? Daddy?" He pleaded as he got up closer to me and looked at me with those lustful eyes of his.
"Of course baby." I said as I put my hand away and let his mouth start kissing the tip of my dick. His hand then proceeded to rub my balls as he started to put my throbbubg member in his mouth. It took him a while before he fully fitted my member into his mouth and his head started going up and down my cock.
"Yeaa baby, just like that." I moaned as he used his tongue viciously. I can feel it all over my dick as he gobbled it up.
I proceeded to hold his head using both of my hands and moved his head quickly as if I'm using an on a hole. He seemed like he enjoyed being used by me and seemed to only think of sucking my cock.
"You love being used by daddy don't you?" I said as I continued using his mouth. He seemed to moan in agreement as we continued.
After a while, I was already cumming in his mouth but while I was in the middle of cumming I pulled out and came all over his face as he stuck his tongue out to get some more of my cum into his mouth. Luckily none got on the dress but his face was all covered in the white slimey liquid.
"Thanks for the meal Daddy." He said as he licked a bit of the cum surrounding his mouth.
"Can you help me now?" He said as he lifted up his skirt and showed me his panties, soaked in a ton of pre-cum.
"Of course. Just turn around." I said as he turned around and I was now hugging him from behind ,my naked still hard cock sitting on his ass. I proceeded to grab his cock and stroked it up and down with one hand while getting into his clothes and playing with his nipples using the other. He seemed to be really enjoying it as he kept moaning louder and louder in pleasure.
"Yes Daddy! Please keep using your slutty girl." He moaned as I kept on playing with his body.
"I-I'm going to cum." Arin moaned as we both kissed each other on the lips
He came in my hand after that as he seemed to start getting back to his senses.
"God. What did I just say." He said as he instantly turned red as his hands covered his face from the post-nut clarity embarrassment. His hand then pulled away from his face to notice that some of my cum was still on his face.
"Well you said that you were my slutty girl and called me daddy." I teased as I handed him a tissue as he wiped his face with it.
"Shut up... We're lucky that we didn't get the dress dirty." He said as he took off the dress and folded it and was now completely naked. I proceeded to do the same and started cuddling with him in bed.
"You're such a pervert David." He said as he layed his head into my chest.
"Hey I wasn't the one getting a boner while crossdressing." I retorted
"S-shut up." He quickly said as he softly punched me on my shoulder. We both laughed a bit before falling asleep together
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"Hey you need to wake up. We're going to be late for the double date." I heard a voice say as I was sleeping
"5 more minutes." I said as I turned my head away and pulled the blanked over my head
"C'mon I already cooked some bacon and eggs for you. Get up or else we're going to be late David." It said again as I finally opened my eyes as I saw Arin already wearing the hair extensions, the dress, the short heels?and had the make up on just like yesterday.
"You look beautiful." I muttered as I looked at him
"S-shut up and get up already." He said, blushing looking all embarrassed as I got up. I quickly got up and took a shower. After putting on some clothes I headed to the dining room where there was my breakfast already prepared with Arin sitting in front of it. I sit down and finished my breakfast while chatting a bit with my boyfriend.
"You'd make a good wife." I said as I smiled while I looked at him
"I-I'm a man alright! I'm not a wife. Besides, I can't even cook as well as you." He said as we got up and headed out the door to the mall. We walked together for a bit as always when I decided to hold his hand.
"David! What if someone sees us!" He shrieked, a bit scared but seemed to enjoy it
"You're dressed up as a girl anyway. Even this close I can't tell you're a dude. We can actually act like a couple in public for a change instead of hiding it." I said as I didn't back down on holding his hand.
"But... actually you're right." He said as he smiled and now also held my hand and moved closer to me and layed his head on my shoulder as he moved my arm to be around his head
"Then let's walk like this." He suggested as I agreed and we were both happy that for once we can act like a couple in public without being afraid of people judging us...