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A Handy Surprise Ch. 03

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Dylan fixes a relationship.
5.3k words
4.66
10.7k
8

Part 3 of the 3 part series

Updated 06/08/2023
Created 03/10/2018
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There's a kind of surprise when you're completely frozen, like a deer in headlights. There stood my sister wearing a pair of jeans with a white t-shirt and a black hoodie. She had luggage beside her and looked utterly shocked with hot white anger flooding her face.

There I was bent over on the couch, wearing nothing but a white laced bra, a pearl necklace and earrings, with makeup on and a guy fucking me from behind.

He was wearing just his brown cowboy boots and was all the way inside me.

"What the fuck Dylan?" My sister repeated.

I couldn't say anything. I thought of the situation and was suddenly extremely embarrassed. I'd been fucking Archie, my mom's handyman while I shouted nasty things, while we recorded it and my sister had just found us mid act. I just didn't know what to say.

"So It's you that's been taking my underwear and clothes." She said as It dawned on her that I was wearing women's clothes. "I thought it was that good for nothing maid that wanted to feel sexy while moping the house, but no, It was my brother, my sissy brother, my faggot of a brother Dylan."

She was the only one that called me Dylan aside from my mom when she was angry. I always preferred Harper but I enjoyed that we had that connection, not that I was enjoying that at this particular moment.

"If I may..." Archie tried to add but was immediately interrupted by Hannah.

"Don't you fucking dare say a thing faggot, I know you, you're my mom's stupid worker. You better get the fuck out of here before I call the cops on you for raping my brother."

"I..." He tried to say. He was shocked as well.

"Get the fuck out. Now!" She screamed.

Archie pulled his flaccid penis from me, gathered his clothes the best he could and bolted right out of the door, before turning the corner he shot a glance at me that said. "I'm sorry!" And disappeared.

That's when Hannah noticed the mounted camera in the living-room. "And you're fucking recording this, you disgust me." She looked like she actually was going to puke. "I'm out of here you faggot, I don't want to see you."

She ran to the kitchen to take the keys for the spare car, I heard Archie drive away in his truck and moments later Hannah take off the house at high speed. I was devastated, I couldn't wrap my mind around what had just happened, moments ago I was blissfully having sex with Archie and now everything was a mess. Why was Hannah here? Wasn't she supposed to be at school till the end of summer? What was she going to do?

I was considering everything when I saw the red blinking light on the camera, I quickly went there and stopped the recording. Now I didn't know what to do, I deleted the file and threw the camera across the room, disgusted with myself, I ran to my room, hopped on my bed, and for the second time this week, cried myself to sleep.

I don't know at what time Hannah came back home, but I heard a knocking on my bedroom door, and her soft voice from the other side.

"Dylan, are you there?"

I didn't answer, I was terrified of her, I just cowered behind a blanket.

"I know you're there, I'm coming in, I just hope you are presentable."

"Wait!" I said, realizing I was still wearing a bra, makeup and jewelry. "Give me a second."

I removed the earrings and necklace as fast as I could and put on jeans and a t-shirt, I looked myself in the mirror and the makeup was smeared from crying, I looked like shit but that was all I could do without going to the bathroom.

I heard the door push open and saw my sister peeking inside, her eyes were swollen and red, It seems she had been crying as well.

"We need to talk." She said.

I nodded meekly.

"You look like shit!" She said and half-snorted a laugh. "Come, let's clean you up." She looked exhausted, embarrassed but calm. I followed her out the door and into the bathroom. She handed me some cleaning pads and I started wiping my face. We sat there side by side for a long time until she said.

"I'm sorry."

"For what?" I asked softly.

"For overreacting," I let her continue, "I just had a terrible week and I exploded with you, I was just shocked to see a guy balls deep inside my older brother." She chuckled a little at the thought. "I've been thinking a lot." For the first time I realized she'd been drinking.

"Were you drinking?"

"I didn't know what else to do," She said as if that made sense. "everything is going to shit."

"I'm sorry too." I said, not knowing how to respond.

"For what?" She responded looking with hazy eyes at me.

"I'm sorry you had to find me like that."

"That's okay, I guess you can fuck whoever you want as long as he's not married and you're faithful, It was just the combination of all the shit in my life right now."

"What's wrong?" I asked seeing her troubled expression.

"Everything." Was her answer.

"Come on, I'm still your older brother am I not? Even if I'm your sissy brother." I said jokingly.

She actually smiled a little after that comment.

"I guess you are, even if you're a sissy."

This time I laughed.

"I found out dad is cheating on mom." She said after a while.

"What?"

"Yeah, but that's not all," She paused for a second as if gathering her ideas and began: "You know I was taking a summer class, well I lied, that class I had already passed, I did it because my stupid boyfriend Tommy asked me to spend the summer with him, so I did. Until yesterday when I went to his dorm room and found him having sex with one of his classmates, a black girl whose name I don't remember. I wrecked his room in a blind fury, I had sacrificed part of my summer for him and he was fucking another girl behind my back."

I gave her a quick hug as soon as I saw she had tears on her eyes.

"So then I call dad to ask him for a flight home, and he doesn't respond. Finally a woman's voice answered, I was shocked but I asked to speak with dad and she handed him the phone 'Danny, darling'. 'Darling' mom hasn't called him that since forever. So he finally talks to me, I ask him about the woman and he says she's his assistant but I know Jenny, his assistant, she's been with him for years and she never calls him darling. So I confront him and he denies everything, says he hired a new assistant because Jenny is sick, when I press on the matter he says 'what do you want Hannah? I haven't got time for you, I have business to attend to.' I asked him to buy me a ticket back home and finally said: 'Have fun doing business darling.' and hanged up on him."

Tears were now flowing across her face, I handed her a tissue to wipe her eyes.

"Thanks, I thought dad would be mad and wouldn't send me the ticket but he did. So I came home wanting to relax and spend time with you, and I find you being butt-fucked by mom's worker. It just was too much, and I exploded and I lashed back on you."

"That's okay." I said and hugged her tightly.

"You smell like mom, but she doesn't wear that perfume anymore, at least not for dad." She sobbed a little and added. "And I guess mom is having her fun as well, when she took me with her to her friend's house there was all kind of talk about 'the boys' and whatnot, even though they're all married women, she tried to downplay it a bit and I didn't get it at the time but now I'm pretty sure they go clubbing for men or maybe hire them."

She looked at me with tired eyes.

"Come on, let's get you to bed, you need to rest." I said as I took her hand and lead her into her room. I helped her get on her bed, I turned around to leave, but she stopped me.

"Please, stay with me Dylan." We hadn't slept together since we were 9 or 8 when our parents insisted it wasn't okay. But we had been very close from a small age.

"Okay 'HenHen', I'll stay with you." I hadn't called her that since a long time ago, that nickname came about when she couldn't pronounce her own name and referred to herself as HenHen.

We slept peacefully for a long time.

When I woke up it was around 11:00 am and Hannah was still asleep in front of me. I got up trying not to disturb her and headed to the bathroom for a nice cold shower, I washed away the stress, the pain and the shame from yesterday, I thought about Archie, what was he thinking. He certainly wasn't gonna come here with the things Hannah said to him. Maybe I should give him a call. I was contemplating all these stuff when I heard Hannah call to me through the door.

"Dylan, you showering?"

"Yes, I'll be out in a minute."

"It's okay, don't worry, you want coffee?" I was never a coffee person but I guess Hannah was a little hangover and she wanted to take the edge off.

"Sure."

By the time I got down to the kitchen Hannah was cradling a big mug of coffee and taking small sips.

"Good morning Dee." She said. She hadn't called me Dee for a while either.

"Morning HenHen. How are you feeling?" I responded. I took a mug of coffee and started sipping myself.

"I'm okay, nothing a college girl my age can't handle. I just have a little headache."

"Want some breakfast?"

"Sure."

I prepared eggs with ham, and orange juice for her, she ate hungrily and then confessed:

"I hadn't eaten anything since yesterday morning, this was really nice. Thank you."

"You're welcome. Want to talk about yesterday?"

"No, it's okay, I'm calm now. As I said I'm not really angry with you, you just caught me by surprise."

"I'm sorry."

"Don't be. Tell me instead what's the deal with this guy."

Over the course of the next hour I told her what had happened this week, trying not to give away too much details away or tell her how much sex I'd had with Archie, but I'm pretty sure she could tell we'd been busy. For one thing It was nice having my dear sister back, since we were little we'd always felt like it was the two of us against the world, and we had just recently drifted apart when we entered college respectively.

"You're such a slut!" Hannah said after I'd told her my story. "You know? I liked teasing him with stuff like having him apply lotion on me."

"I know, he told me. He actually confused me with you once, I was sleeping by the pool"

"Really, that's funny. Remember when we were 6 or 7 and we used to switch clothes between us midday just to screw with mom and dad?"

"Yeah, I remember, our 'nana' Miri could always tell us apart, and she'd chase us around the house until she caught us both and make us change back into our clothes. She was real nice with us"

"She really was. So..." Hannah said pausing a little before continuing, "are you gay or..."

"I don't know," was my answer, "I'm not sure, I mean..."

"I'm sorry, I didn't mean to pry, I just got curious. You don't have to answer."

"That's okay, I guess if someone can help me figure it out, that would be you." I gathered my thoughts and then went on. "I mean, I like dressing like a girl sometimes."

"I noticed that, but do you like men?"

"Not always, but I sometimes fantasize about being with a guy. Especially when I'm dressed up."

"So you like to cross-dress then?"

"I guess so."

"And with Archie, how do you feel?"

"That's a tough one, I like being with him and not only in a sexual way," I blushed heavily, Hannah chuckled, "he makes me feel nice, and when he looks at me It's like I'm the most important person for him, he makes me feel wanted and sexy."

"Oh my god, I think you're falling in love with him."

"No I'm not!" I said while blushing. "I just like him."

"Oh my god, you totally are."

"I said I'm not!"

"Alright, have it your way Dee. Thanks for the breakfast, I'm gonna go take a bath now, I smell terrible, I'll talk to you later 'sister'." Before I could call her back for it, she took running upstairs.

Later that day Hannah came to me and said:

"So, when are you going to let me see my sister."

"What do you mean?"

"You like to dress up right? Let me see you dressed up."

"You kidding me, I'm not dressing up for you."

"Come on Dee, I already saw more than I intended yesterday and you had a dick up your ass." I almost spilled my drink when she said this.

"What?"

"I'm just saying Dee, come on, let me see you fully dressed!" She was making her puppy-eyes, the ones she knew no sane person could resist. "Pretty please! I'd love to."

"Fine." I said, giving up, "but I'm wearing your clothes". As I said that she stuck her tongue out.

I went upstairs and started changing into girl's clothes. I wore a plain black set of panties and bra. I placed a pink tank top on with the words 'LOVE' printed on the chest, and a pair of jean shorts that showed off the curve of my butt. I then went to my sister's dresser and started applying makeup, something natural looking but that enhanced my eyes and lips, as I was sure these were my greatest asset. I was applying the final touches of my mascara when I was interrupted by a shout behind me:

"Oh my god! Harper Dylan Roberts, you are my sister!" Hannah exclaimed triumphantly.

"You were supposed to wait downstairs."

"I got impatient and came to see you. Come on, let me see you."

"Hold on!" I said and finished putting on my mascara. I got up and turned to face her. She was incredibly surprised.

"You do look like me Dee, I can see how someone would confuse the both of us." She went closer to me and turned me back around to face the mirror.

I could see it as well, Its like we were twins maybe not identical but no one would deny we were sisters at least. Her features were more delicate and her hair was longer, it reached her back but besides that we looked very much alike.

"Oh my god, you're such a tease," she commented when she saw the shorts I was wearing. "You do know how to enhance your attributes, and where did you learn to do you makeup like that?"

"Internet."

"Of course!, well you look amazing. Do you call yourself something when you're dressed up?"

"Not really, I guess Harper can be a girl's name as well."

"I guess you're right, I'll just start calling you Dee again. Now come, I'm starving, I'll even help you cook this time."

That weekend we spent like old times, hanging together, the only difference being that I was dressed as a girl the whole time. On Sunday however, Hannah got an idea to tease me.

"You've been wearing some of my clothes for a while now, haven't you?"

"Yes, so what?"

"Well, they're yours now."

"I can't!" I exclaimed.

"Yes, you can and you will take them. And you're going to buy me some new clothes while you're at it."

"I knew there was a catch!"

"Oh, there always is, the catch this time is we'll go together to the mall and you'll buy me new clothes."

"Fine, I'll go change."

"No!" she said, "you'll go as you are right now, dressed like a girl."

"You're kidding right? I can't leave the house dressed like a girl."

"Didn't you say you went grocery shopping this week dressed up?"

"But I went all the way across town so no one would recognize me."

"That's okay, no one will recognize you. I didn't at first when I first saw you. Now get in the car, you're driving." I didn't believe what she said about not recognizing me but I complied with her.

The drive to the mall was nerve wrecking for me.

"What if someone recognizes you and asks who am I?"

"Then we'll say you're my cousin, that'd explain it."

"And if the know our uncles?"

"Then we'll say its you Dylan, dressed like a girl."

"You serious?" I said, completely terrified.

"Of course not silly, no one will notice you, I promise."

We arrived to a local mall around 3:00 pm and once again I had to collect myself. I wasn't dressed provocatively or anything, more like a regular girl with tight jeans, a pink t-shirt and sandals but my nails were painted red and my hair braided with Hannah's help.

We browsed a little in the mall and Hannah seemed to relish in my embarrassment, but little by little I started getting more comfortable. Once Hannah blew a kiss to a group of guys and they went crazy, I on the other hand would cower immediately. I guess to them we looked like sisters, an extrovert flirty one and a shy one.

We stopped in front of a lingerie store and Hannah suggested we go inside. I begrudgingly did so. She approached the attendant and said:

"Hi dear, my sister here is looking for something to impress her boyfriend on their anniversary."

"Sure, my name is Andrea and I'll be happy to help you."

I was standing there blushing fire red, not knowing what to say. I was afraid Hannah would do something like this from the beginning. Andrea was really charming and she was used to handling nervous customers, she helped Hannah pick out some cute lingerie and she made me model for her in the dressing rooms. We bought a pair of really sexy sets which set me back quite a bit, but Hannah insisted that it was a special occasion and I shouldn't spare money if I wanted to look ravishing. This went on for the rest of the day, if Hannah liked something for her, she made me model it and if she liked the way it fit me, she'd make me buy It.

We returned home late and I was exhausted, I just wanted to lay on the bed and sleep for the rest of the night but Hannah insisted we should go out clubbing tonight.

"Come on!, I'm so tired, you've drained my energy and my bank account." I said.

"Well, maybe you're not really used to it but most of the times, a lady doesn't have to pay when she goes out clubbing. Now stand up and take a shower, we're leaving in an hour."

She pushed me off the couch and practically dragged me inside the bathroom. I showered and it helped me fight the weariness. When I got out of the bathroom and into my room I found an outfit set for me on my bed. It was a dark blue cocktail dress that hugged my chest closely and opened up at my hips helping define my figure. Underneath I wore a black bra and black bikini panties taking great care to tuck my penis. I also put on a pair of wedged high heels. Finally I joined my sister in front of her dresser and she actually catcalled me:

"You devil! Guys are going to be all over you tonight."

We helped doing each others makeup, she actually gave me a couple tips she used herself, and was surprised watching my skills.

"You're actually pretty good at doing your makeup, better than some girls I know."

She drove us to town and to the front of what looked like a popular dance-club, there was a line of people waiting to enter and loud dance music blasted from the inside. A valet guy took the key from Hannah and couldn't help himself checking her out. Hannah walked confidently to the bouncer, leaned in closer in what seemed like a whisper and he immediately raised the chain and motioned her in, she in turn grabbed my hand and pulled me inside.

My senses were immediately assaulted by the loud music, the smell of sweat and alcohol, and the warmth emanating from the large group of people. Hannah lead us to the bar and immediately ordered several Jäger shots. We hit the dance floor and within a few seconds there were some guys trying to dance with us, Hannah easily dismissed them and following her lead I did the same, once the alcohol hit my system I left myself flow with the music and the energy of the place.

Once we went back to the bar, there wasn't a guy there that didn't want to buy us drinks, they asked if we were twins, and then went through the usual pick up lines, the ones about fallen angels and whatever, It was actually kind of funny seeing this pathetic attempt as a girl. I took the drinks they offered and smiled politely but didn't lead them on. Until I noticed someone that took my breath away, I left the guy that was talking to me and walked directly to him.

He was shorter than me with a wide chest and strong arms, his tanned brown skin shined under the strobe lights, he was wearing a white shirt that hugged his chest tightly and his sleeves were rolled up to his elbows. His dark hair was combed slick and wet, he was wearing a pair of dark jeans and leather brown cowboy boots. I glided to him like a magnet, it was just me and him in the club right now.

12


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