Fall into His Arms

It was a windy Autumn Friday in Manhattan and I had just left class and was on my way to JC Penny's to do some shopping. I was excited and bouncing on my heels as I thought about my upcoming spree when I heard a deep, almost familiar voice call out behind me.

"Jesse! Is that you?"

I turned and saw someone I hadn't seen in years but still recognized immediately. It was Bobby, one of my friends from grade school. I hoped that my expression matched the one on his face which was delighted and surprised.

"Wow! Bobby! It is so good to see you!" I exclaimed as we gave each other a hug.

"What are you up to?"

I asked as we both stepped back from the embrace.

"Well, I just got off work." He replied, "We should get a coffee somewhere and catch up."

Seeing as I was done with classes for the day I agreed, and we walked around the corner to a Starbucks. As we walked we brought each other up to speed on what was going on in our lives. Bobby had graduated college and was working for a small sports magazine covering baseball, that made sense considering he was a great athlete growing up. I, on the other hand, was starting my first year in a small theater school in Manhattan. As we sat down with our coffees Bobby asked,

"So what are you up to tonight? Because I have no plans and it would be great if we could hang out this weekend."

"Well...ummm..."

I stuttered, trying to thing of something to say besides the truth, because the truth was a little embarrassing. The truth is, before I ran into Bobby, I was on my way to JC Penny's to do some shopping. But not the kind shopping he might expect. I wanted to find some new lingerie, a dress or two, and anything else cute I saw in the women's section.

Since I was a teenager I have enjoyed dressing up in girlie outfits. I would even put on make up and shave my legs from time to time. I always did it alone and would take pictures of myself that I would send to hot men I met on the internet. I liked going to this specific JC Penny to do my shopping because the women's section was in the basement where it was usually quiet and I could pick out sexy outfits without feeling embarrassed.

I snapped back to the present. Feeling flustered and unable to come up with a lie, all I managed to squeak out was,

"Well, nothing really."

"Nothing?" Bobby asked raising his eyebrows, "You looked like you were in a hurry when I saw you, where were you heading?"

I became nervous again, wondering if I should just tell him the truth.

I normally wouldn't let any of my friends know this secret but Bobby was different in one very big way. My enjoyment of feeling girly actually began as a child in elementary school when I used to go to Bobby 's house for play dates. Our favorite game to play was house and he was a bossy boy growing up so he would be the one to choose our roles every time. And every time without fail he would choose to the play the role of husband and make me play the role of his wife. I would have complained except for I didn't mind being his wife in these situations. It meant I got to wear one of his moms old dresses, put on her lipstick, and talk in a high pitched girly voice for the whole game.

Apparently I had spaced out thinking about our play dates because Bobby snapped his fingers and joked,

"You still there? What are you thinking about that has you smiling like that?"

I immediately blushed, realizing that I had a dreamy, dumb look on my face from picturing us as husband and wife playing house. I was flustered and without thinking I blurted out the question that I was afraid to ask.

"Do you remember those play dates we used to have in elementary school? And how we used to love playing house?"

I immediately regretted asking it, thinking it was random and would throw Bobby off, but to my surprise he replied,

"Yeah I do, I remember you used to love being the wife and dressing up in my mom's clothes."

I felt embarrassed that he remembered it that way and countered,

"Well I only did that because you told me to!"

He smiled and began to blush a little himself admitting,

"I guess I would be lying if I said I didn't enjoy making you dress up and be my wife."

So far the conversation was playing out like a fantasy and I guess that made me feel bold because after a moment I replied,

"Well I have a confession to make."

After saying this I realized it was too late now and there was no going back.

"What is it?" He asked with a curious look on his face.

I released a nervous sigh,

"Well, I did enjoy wearing those dresses and make up. In fact I still enjoy it and I do it from time to time when I'm home alone. So when you asked me where I was heading, I was actually heading to JC Penny's to buy some stuff to put on when I get home tonight."

I looked down at my coffee to hide my red face, I can't believe I had just told him that, I'm such a chattermouth.

To my absolute surprise, however, Bobby remained relaxed and casually replied,

"Well do you want company? I could help you pick out some stuff that would look good on you."

Okay, I thought trying not to freak out, if he still thinks I would look good as a girl then maybe I have a chance.

"Sure," I replied with a smile, "I would like that."

So we head off towards JC Penny's and I briefed him on what I planned on buying as we walked. Suddenly I felt much less nervous and much more excited, and I noticed without that even thinking about it my voice had become higher and more squeaky.

"Well I was planning on just getting a few things when I was alone but are you going to want to see what I look like all dressed up?"

"Yeah I would be interested in that." Bobby replied with a smile.

"Okay then," I continued, "I'm going to go all out then because if you don't like what you see I'm going to be embarrassed."

"What does 'go all out' mean exactly?" He inquired.

I smiled and began rattling off my shopping list, "I'm going to need a nice set of lingerie, at least one dress and one skirt with a top to match, stockings, shoes, and make up."

"Oh," I added thinking as I talked, "I will also get a women's razor and some shaving gel so I can shave my legs."

Bobby looked impressed, "Shaving your legs? Wow you really are going all out." I blushed and nodded, hoping I wan't acting too excited about all of this.

We walked into the store and I quickly lead him to the lingerie section, where we picked out a matching set of black lace, low rise, bikini panties and a bralette. We picked up simple white school girl socks and just for kicks we also got a black lace babydoll nightie. Next we went to the dress section and picked up a black lacy sleeveless dress that ended halfway down my legs. We also picked up a black flowery dress with a frilly bottom and a tight top with three quarter length sleeves and an open collar to show off my exaggerated collarbone. I bought a pair of two inch leather heels that were also black.

Our next stop was the make up section, Bobby let me make the decisions here because I promised him I knew what colors looked good on me. To set off all the black clothing I bought some scarlet red lipstick and a slightly darker red lip pencil to outline my lips with. I went with some subtle reddish pink blush and black mascara. Lastly I picked up some smokey blue eye shadow. The last stop before checkout was the women's grooming aisle, were I got a razor and some apricot shave gel. To make sure I smelled as girly as I looked, I got some apricot body oil for after I shaved. I also got shampoo and conditioner deciding it would be good to wash and condition my hair, which was shoulder length and would really complete my look. Bobby insisted on paying for it which made me feel girly so I let him. Bags in hand, we set off for my apartment.

"I live alone in Brooklyn so privacy won't be a problem" I assured Bobby, trying to be discreet as I brushed up against him on the subway.

"Great." He said with a smile and to my extreme surprise he moved behind me and grabbed my butt. It took everything in me not to squeal out loud and instead I turned to him, beet red, whispering,

"OhmyGod! You snuck up on me!"

With a devilish grin he said, "I don't know what you're talking about."

We quickly exited the station and were in my apartment elevator in minutes.

"I'm going to need some time once we get up there to get ready so you can just wait on the couch and watch ESPN or something." I instructed.

He laughed and replied, "Aww I wanted to watch you get dressed."

It was my turn to put on a devilish grin, "No, no, noooo." I taunted, "You don't get to see me until I'm ready for you."

Bobby just laughed and said, "Alright fine, I can wait."

We entered my apartment and I showed him the couch and the TV and then went back to my bedroom.

I took the grooming items back down the hall and into the bathroom, which was between the living room and my bedroom, saying as I went, "I'll be out in a little while, make yourself at home but no peeking!"

Pleased with my feminine remark I stepped into the shower and turned on the water.

The first thing I did was wash my hair and condition it, then I put it back up into a bun and let the conditioner do it's work while I focused on the rest of my body. After soaping down quickly I began to shave, starting with my legs. I lathered up some of the apricot shaving gel and picked my leg up, placing my foot on the bench in my shower just like I had seen women do it in the commercials. Feeling very girly, I began at the bottom and worked up in smooth strokes. It took a while to get each leg done but the rest of my body was easy, seeing as I wasn't very hairy and kept my face shaved anyways. After going back and getting any spots that I missed, I soaped down again, amazed at how smooth my skin felt now. I rinsed the conditioner out of my hair, and turned the shower off feeling very sexy already.

My confidence quickly turned to horror when I reached towards the towel rack and realized I had forgotten to bring a towel into the bathroom with me. There was a clear view of the hallway between my bathroom and bedroom from where Bobby was sitting and I was going to have to make a run for it, naked and dripping wet, right in front of him. I counted to three quietly and then opened the bathroom door as quietly as I could. I stepped into the hallway looking in Bobby's direction to see if he noticed me and to my embarrassment he looked up and first made eye contact with me before looking me up and down. I shrieked as if I had just seen a mouse and ran on tiptoes back to my room, feeling my wet ass bouncing against my thighs as I went.

I closed my door and locked it as soon as I got to my bedroom but I could hear Bobby catcalling from the living room.

"Whoo Whee!" He exclaimed, laughing, "What a sight!"

"I forgot my towel, I'm so embarrassed." I moaned.

But to tell you the truth, after hearing his reaction I was more bashful than embarrassed and smiled to myself. I toweled off my body and then wrapped my hair to help it dry without getting to frizzy. After putting my hair up I was ready to get dressed.

I laid out all my clothes and decided that the best look would be the panties and bralette with the flowery skirt. That way, I could put my hair in pigtails and go for the school girl look. I covered myself head to toe in the body oil, applying a little extra to my ass and legs to give them that sexy shimmer effect. Then I stepped into the panties pulling them halfway up my hipbones. With my bony hips exposed I looked especially feminine. I put on the bralette, adjusting it until it fit just right and pulled the white socks up each leg, they fit perfect ending right above each knee. The next step was to step into the dress, which had a zipper in the back that I couldn't reach. Oh well, I would let Bobby zip it up when I was done.

Before doing my make up I had to make sure my hair was fully dry so I could put it up. I split my hair into two equal halves, using a comb to make a part down the middle of my head and then pulled each half into a high ponytail. They were very tight and it hurt a little bit but the look was worth it. I was almost done.

With my clothes on and hair done. on it was time to move to make up. I began with my eyes, pulling the mascara brush out of the bottle and fluttering my eyelids onto the brush from every angle, after a little cleaning up my lashes looked thick and long. I then lightly applied the smoky blue eye shadow to my eyelids, using just enough to make my eyes look a littler wider and rounder. The next step was lipstick, I rolled the stick across both top and bottom lips and smacked them a few times to make sure the scarlet color was evenly distributed. The lip pencil was a nice touch and I used it to outline my lips, making them look a little fuller than they were. Lastly I lightly applied blush to each cheek, not so much that you would notice act first glance, but enough to achieve the school girl look that I was going for.

Before leaving my room I went to the mirror and made sure I was pretty enough to be seen by him. The pigtails along with the make up made my face look very feminine and the wide neck of the dress showed off my exposed collarbone which only added to the look. I gave a quick spin and then stepped into my heels, taking a few practice steps and swaying my hips like I thought a runway model would. Time to let Bobby see me as a sexy school girl.

"I'm readyyyy, sorry it took so long!" I called through the doorway.

Bobby replied, "Oh it's quite alright, are you going to come show off the clothes I bought you?"

I beamed and answered brightly, "Yes sir!" And taking a deep breath I opened the door stepping out into the hallway.

I made eye contact with him as I swayed towards him, desperate for his approval. I got what I was looking for and upon seeing me all dressed up, Bobby 's jaw fell open. In my best girly voice I asked,

"Can you zip up my back?"

"Su... Sure."

He stammered and carefully zipped up the back of my dress. He sat back down and I turned my back to him, sticking my hip out in a pose. I then playfully wiggled my ass back and forth and looked over my shoulder at him, wrinkling my nose and smiling mischievously. I then did a spin and a curtsy and moved to the couch and sat down next to him, crossing my legs and folding my hands obediently in my lap.

"What do you think?" I asked, giving him a wide eyed hopeful look.

"I think... I mean you look... you look amazing. You're beautiful." He stammered still looking me up and down.

I blushed and threw my arms around him, careful not to mess up my make up, "Awww! Your so sweet! Thank you, I really wanted to impress you."

"Well you definitely did that, I mean you really look like a girl." Bobby marveled. "Your skin looks so smooth, do you mind if I touch it?"

Wearing those feminine clothes and receiving all those compliments had begun to make me horny and I boldly replied,

"You can touch whatever you want, Bobby."

At that he reached out and stroked my exposed collarbone he proceeded to move his hand down my side to my hip,

"You have a perfect girlish figure with your slender waist and bony hips." He said absentmindedly as he moved his hand around my body.

"Thank you!" I replied in a high pitched voice.

Bobby didn't seem to hear me however and kept his eyes fixed on my body.

"Your legs are so long and thin, can you stand up for me?" I obediently stood bending one knee slightly inwards like I had seen the hentai school girls do so many times. I knew I looked sexy and it was really turning me on. I was starting to need more and decided I might as well try to get it.

Bobby must have been thinking similar thoughts because this time without asking, he reached out and touched my exposed thigh.

"Your skin is so smooth it's incredible," he remarked and then he began to move his hand up under my dress towards the place that my thigh meets my ass. He reached it and then pulled his hand back down but at that point his intentions were clear. I put on my best seductive grin and asked,

"Do you want to see the lingerie you bought me?"

He nodded, cleared his throat and said, "Yes I would like to see that."

I hadn't asked him but I was guessing that he had never done something like this as an adult and decided I was going to have to take charge from here on out to get what I wanted. And what I wanted was his cock in my mouth. I had never sucked cock before although I had thought about it numerous times and I realized that this was my chance. With that I showed him my back again, bending over to unbuckle my heels giving him a glimpse of my ass under my dress before standing back up.

"Can you to unzip me sir?" I asked, arching my back and shaking my shoulders back and forth like a school girl waiting for a piece of candy.

Without a word, Bobby stood up behind me and unzipped my dress, pulling each side off my shoulder and releasing my arms. At this point all it took was a little wiggle of my hips and legs for the dress to fall around my ankles and all of a sudden, just like that, I was standing in front of Bobby in my panties and bralette. I looked over my shoulder giving another playful smile and watched him admire my ass in the lowrise panties which showed the very top of my butt crack. After a few moments I spun around and clasped my hands in front of my crotch, hiding my penis but giving him a view of my sharp hips and exposed ribs.

After a prolonged silence I asked,

"So do you think I could be your wife if we played house?"

He quickly replied, "Oh yeah, I think you would make the perfect wife."

I decided it was time to start dropping hints.

"Well now that were older, what would I do for you as your wife in this game."

Bobby looked up at me with a nervous expression,

"Well... what do you think?" He asked.

I answered with a subtle smile, "Well you just had a hard day at work, how bout I help you blow off some steam?"

With that I took his hand and gestured for him to sit down,

"Can I sit in your lap husband?" I asked.

"Yes you may." he answered, and opened up his legs to allow me to sit.

I sat on his right leg, I felt something hard next to his thigh. I turned to face him, at this point our faces were no more than a few inches apart, and I whispered,

"It seems like your excited, can I help you relax?"

Bobby took my by surprise when he grabbed my ass with one hand and the back of my neck with another and pulled me in for a passionate kiss. After a a minute of French kissing he began to stick his tongue deeper and deeper into my mouth and I began to suck on it, giving him a hint of what was to come. We stopped kissing and before he could say anything I began to bite his neck, I quickly pulled his shirt off and kissed his chest a few times, leaving lipstick marks each time. I had waited long enough, it was time to get what I wanted. I slid off his lap and ended up facing him on my knees with my ass resting on my heels and my hands in my lap.

I looked up at him through my lashes, raising my eyebrows to look extra girly and proceeded to undo his belt and remove his jeans. Throughout all of this Bobby didn't say a word but his feelings were made clear when I pulled the waistband of his boxers down and his fully erect cock popped out, flicking precum on my cheek as it went. I smiled and licked my cheek before wrapping my hand around the bottom of his shaft and admiring his girthy penis.

"Wowww." I gushed, "Your cock is huge."

It seemed like he was about to say something in response but all Bobby did was moan and tilt his head back. I realized he might not last much longer and quickly got to work. I began by licking up and down his shaft making sure it was slippery enough for me to move my hand up and down it while I worked on his head. I lapped up the remaining precum like it was milk in a dish and heard an even louder moan escape his lips as I did. Once I had finished cleaning up the tip of his cock, I parted my lips and slowly slid my lips down his head. Once I reached the bottom I pulled my mouth back off and repeated this motion a few times, even rotating my head as I did. Now it was time to see how much of his wide, veiny cock I could actually fit down my throat without choking. I lowered my head, letting my lips slide over his head and onto his shaft. I got less than an inch down before I had to come back up for air. Sucking cock was a lot harder than I thought.