Thursday, November 16, 2017
Wednesday, November 15, 2017
When I started to write this caption, I had no intention of it being this long; over four pages. I wanted to give a back story on how Andrew's sister tricked him into becoming Ashley; then an epilogue seemed fitting to show how Ashley adjusted to becoming a sissy. Please read and I hope you enjoy.
*ring ring, ring ring
Picking up his phone, Andrew saw that his sister was calling him. He hit accept and placed the phone between his ear and shoulder, while playing Xbox. “What?! I’m busy.”
“Whatever Dork. It’s Thursday night, you are probably in your boxers, eating Cheetos, and playing Xbox. I need a favor from you.”
“Not going to happen.”
“Oh I think you will change your mind or I will tell Mom about that thing you did with her you know what.”
“You had plenty of time to tell her that, that was like fifteen years ago. I am sure she has forgotten about it by now.”
“Are you sure?”
“OK, what do you want?”
“Remember that time when you were eight and I caught you wearing my dance uniform?”
“And remember when you were, I think thirteen and I caught you wearing my cheerleader uniform?”
“And remember when I caught you in my wedding gown the week before the wedding; you even had on my bridal lingerie.”
“You were so pissed at me” he said laughing laughing.
“And remember that time you wore that little black mini dress, around my apartment while Ben and I were at his parents for the weekend?”
Pauses his Xbox “Wait, I never… you never were supposed to know about that. How did you find out?”
“It’s called video surveillance; Ben, his parents, and I all got a kick watching you taking care of the cats, wearing my black mini.”
“That was like three months ago. We’ve gone out together since then. Ben and I have played golf. And no one has said anything?”
“Well we didn’t want to hurt your feelings; besides, Ben has known about your cross-dressing ever since we started dating. As a matter of fact, I think I told him on the first date. I’d just caught you in one of my bridesmaid’s dresses.”
“Great, now I feel like a loser.”
“Your are not a loser lil brother, your are just a sissy and there is a difference. We love you; even mom and dad don’t care.”
Trying to hold back his tears. He didn’t even question his sister calling him a sissy “So what is this favor?”
“Well Ben’s college roommate, Carl is coming to town this weekend and I had set him up with Chrissy (their cousin) but she got Mono all the sudden. Then Ben jokingly said, ‘we should set him up with your sissy brother…’
Interrupting her “He actually said ‘sissy brother?’”
“Well you did leave your Blogger account open on our computer, you may want to clear your history the next time. Anyway, Ben has mentioned you to Carl…”
“Wait! Carl knows too?”
“I don’t think that there is not anyone that does not know.”
“Well that explains all the Victoria’s Secret and Forever 21 gift cards from Grandma.”
“Probably, a-n-y-way turns out that Carl is bi-curious and has always wanted to go out with a cross-dresser. And that is where you come in, I’d like you to be Carl’s date for the weekend?”
“Weekend? Meaning Friday, Saturday, and Sunday?”
“And Monday morning too, you are taking him to the airport.”
“So I am supposed to be a girl the whole weekend and Monday? What am I supposed to do for clothes?”
“Well you said Grandma sent you all of those gift cards; so you either still have them or you’ve used them. Besides we are the same size, so I’d say clothing is not a problem. And from the pictures I’ve seen on Crossdressers.com you can transform yourself into a beautiful woman - you really need to clear your history next time.”
After a long pause “Can I borrow that black mini dress tomorrow night?”
“Tell you what, I will give you that dress if you agree to this.”
“Fine, I’ll be over tomorrow afternoon to get ready.”
“Why don’t you come around lunchtime, it will give us some sister bonding time. Carl’s flight gets in at 5:30pm and Ben is picking him up. They will met us here.”
“I’ve got a funny feeling about this but I’ll see you tomorrow.”
Andrew hung up the phone, stood up, and dusted the Cheetos dust of his fingers onto his boxer shorts. He walked into the bathroom and stared at himself in the mirror for a few minutes - he knew what he had to do. Under the sink he grabbed the shaving cream and a razor, then walked over to the bathtub, stripped naked and sat on the edge; he lathered each leg and shaved all the hair off - followed by the arms. He used an electric shaver in the nether region and cleaned up with shave foam and razor. Butt naked, he walked to the closet and pulled out a Rubbermaid tub full of his girly clothes. On top was one of his chastity devices; he placed himself in, locked it, and put the keys in the drawer in his nightstand. Andrew slid on a pair of white cotton panties and put on a white bra with pink polka-dots; he inserted his B-cup breast forms, then put on a pink linen full length nightgown..
He then started to make piles on the bed he was going to pack for the weekend: 4 pairs of jeans, 6 pairs of shorts, 5 skirts, 13 different tops, 4 sundresses, 6 swimsuits, 9 bra/panty pairs, 2 black and one white corsets with matching panty, 7 pairs of stockings, 8 pairs of tights, 9 nightgowns, and 3 dresses for Sunday brunch; not to mention the 4 pairs of black heels, 10 casual shoes, and five pairs of flip-flops. Plus all of his wigs (3), jewelry, and makeup.
The next morning he got up and did the three Ss - shit, shower, and shave (his legs and arms again). With his chastity was still firmly secured, Andrew put on a pair of yellow silk panties and matching bra; the breast forms had extra adhesive applied. He slid into a pair of boot-cut denim jeans and put on a white camisole, which he tucked into his jeans. Then put on a red/white checked flannel long sleeved shirt, he left the top three buttons open to show off his cleavage. Finally a pair of black and white polka dot socks and a pair of women’s cowgirl boots. His suitcase was packed, he took one final look in the mirror to adjust his wig and makeup touch ups - all was good; he took one final deep breath, then walked out the door.
Andrew had driven before in girly mode but it was always between 2 and 4 a.m.; this would be his first day time trip. The thirty-five minute car ride was uneventful; as far as he knew, no one gave him a second look. He pulled into his sister’s driveway, put the car in park, and shut the engine off. His eyes were closed - ‘am I really doing, am I really doing this’ he thought to himself over and over. He was awakened by his knocking on the window; she was acting very giddy. Andrew stepped out of the vehicle.
“Oh my goodness, you came as Ashley. I cannot believe it. Hi Ashley, I’m your big sister” Allison said as they hugged. “Where’s your bag?” Ashley used her remote and popped open the truck and Allison took it out and carried it was they walked to the house, with their arms around the other’s waist. “We are going to lunch, then we have a nail appointment at 1:30 - my treat. We should be back by four and that should give us plenty of time to get ready. The guys are taking us to a new Brazilian steakhouse. I love this shirt, who knew my little sister had such good fashion sense.”
“I’ve always had good fashion sense.”
“Oh come on. Remember you once thought it was “fashionable” to wear wear Army fatigues to school.”
“Let’s get going. I’m starving.”
After lunch and the mani/pedi, the girls came back to the house to get ready for their dates. Ashley was in her room getting ready; she had taken off her bra and panties and had put on one of her black corsets with matching panty. She was getting her breast forms adjusted when Allison walked in with the Little Black Dress and she saw Ashley’s chastity device through her panties. “O-M-G! I was not expecting that” pointing to the lock hanging out the top of undies.
“Well I figured if I am going to be a sissy this weekend, I might as well play the part.”
“And from what I have read in your captions, all good sissies suck cock on their first date. Do you have the key for that thing?”
“Yes, but it is at my apartment. Guess I figured I didn’t want to worry about “it” doing something.”
“Who would have thought that me and my little brother would have a dick in their mouths tonight. Well let me know when you want me to help zip you up.” Allison giggled laying the dress on the bed.
Ashley finished applying her makeup and did some touch-ups on her wig. She opened a pack of fresh tights and slid them on. She stepped into the dress and zipped up as much as she could before asking her sister for help. Allison looked gorgeous as always, she zipped up the dress and gave her sister a hug from behind. Both were looking into the mirror “We really do look like sister. I love you sis.”
“I love you too. I need some alcohol.”
“I can arrange that.”
Allison cracked open a bottle of Merlot and poured Ashley a glass, she had just sat on the edge of the couch, when Ben and Carl walked in. Allison went over and gave him a hug and kiss on the cheek, Carl squeezed her ass - that was their thing. “Carl this is my sister Ashley.”
Ben called an Uber that picked them up thirty minutes later. The four had a great time at the Brazilian restaurant and the piano bar for after dinner drinks. Another Uber brought them back home, and another bottle of Merlot later, it was bed time. Carl and Ashley went into their room, and Carl shut the door. “Can you help me with this?” said Ashley pointing to the zipper.
“Sure, allow me.” Carl replied, slowly unzipped the dress with his right hand, reaching around her holding her right breast with his left hand, while kissing the nape of her neck. The dress fell to the floor around Ashley’s ankles. Carl was standing so close to her, she could feel his erect cock through his pants. She turned around and they were staring each other face to face. “I don’t want you to do anything you don’t want to do.” Ashley grinned, gave him a small smooch on the lips and gave a small grin. She then got on her knees and unzipped Carl’s pants; Carl was commando. His gargantuan penis plopped through the opening in his pants. Ashley gave it a few strokes then inserted the appendage into her mouth. Carl held the back of her head, as he mouth fucked Ashley. Seventeen minutes later, when Carl said ‘I’m about to cum’, Ashley made sure her mouth was at the base of his cock, so she could get his entire load in her mouth and down her throat. After he ejaculated, Carl did what most guys do; took off his suit, threw it over a chair, and went to bed wearing his only his T-shirt, started playing on his iPhone.
Still in her corset, panty, and tights Ashley grabbed some toiletries and a nightgown, then made her way to the guest bathroom. She slid off the tights and lingerie, and looked down at her tiny ding a ling locked away; at this time she didn’t if it was never free again, she knew she was a sissy for life. She brushed her teeth then put on a comfortable pair of granny panties and a full length spaghetti strap nightgown. When came out of the bathroom, Allison was waiting for her and gave her a great big hug.
“Carl just texted Ben, I’m so proud of you. You will always remember your first blowjob. Mine was with Michael Davis at Junior Prom.” She gave her sister another hug. “ Oh I wish we could have been sisters a lot sooner.” She walked Ashley back to her room.
Standing outside the door Ashley said to her sister, “Thanks for doing this but I do have a question and please be honest, did Chrissy really have Mono or was this something else?”
“I do not know what you are talking about. Oh did I mention that we are meeting Mom, Dad, and Chrissy for brunch Sunday morning so wear something that won’t embarrass them. But tomorrow we are going horseback riding and a picnic.
It is Monday morning, Allison and Ben have gone to work, Carl had just gotten into the shower, ‘it’s now or never’ thought Ashley. She unclothed and got into the shower with Carl. The two soaped and cleaned the other’s body and made out until the hot water was gone. They were out of the shower, toweling off.
“Since we are alone now, there is something I’ve been wanting to do to you since Friday night” Carl said reaching for something in his shave kit.
He spun Ashley around so they were both facing the mirror in the bathroom. He uncapped a travel size tube of KY jelly. She gave a nod of approval. Carl smeared a line of gel from the tip of his dick to the base, gave a once over rub in, and shoved his manhood into Ashley’s virgin ass. He began thrusting back and forth, Ashley had never felt this euphoric and she begged for Carl not to pull out but to cum inside her - he did what he was told. “As you wish.” he said.
Ashley turned around and gave Carl a kiss, while cleaning his cock with a wet wash cloth. “When can I see you again?” begged Ashley.
“I can swing back through sometime next month.”
“I’d like to do this again sometime. Maybe just the two of us. Another long weekend. A cabin in the mountains, so I can scream as loud as I want when you fuck me again.”
“That sounds nice. I’ll make some calls.”
On the way to the airport, they stopped by Ashley’s (Andrew’s) apartment. “Come in for a sec, there is something I want to give to you.” She went to her nightstand and grabbed the chastity lock keys. “These are the only two keys for the lock and I want you to have them. I’m officially your property now.”
“Well then, how about one more blowjob before my flight. Flying always makes me stressed.”
“As you wish.”