A Halloween Love Story

Thank God it was Friday. Sam had had one hell of a week. Even his key seemed tired and frustrated as it refused to open the door of the apartment and he had to give it an extra twist to get it to open.

“Hey Sam, what’s for dinner?”

Sam rolled his eyes and groaned as he remembered he was meant to be bringing the groceries home and cooking dinner. It had been such a bad day at the office that he had clean forgot.

“Oh man! Sorry, I’ll have to order a pizza, it’s just been the worst day of a horrendous week. I’m really sorry!”

Jim entered the room and smiled at him. He was such a good mate Sam knew he wouldn’t be mad and he wasn’t. He came over and gave him a big man-hug.

“Don’t you worry, I’m sorry to hear you’re having such a dismal time. Look I’ll order a pizza, the usual?”

“I’ll do it Jim.”

“Nope, you just go sort yourself out and relax. Usual?”

“Yes usual! You’re just the best buddy! I owe you one!”

“Beers?”

“Actually I really fancy wine, have we got any?”

“Of course, I’ll pour you one.”

Jim was such a great flatmate and the only downside was his girlfriend who came to stay most weekends and was messy, rude and not even that attractive. Sam didn’t mind too much though as Jim always cleaned up after her and they tended to stay in his room most of the time or be out somewhere. Both their rooms were en-suite, so she didn’t even get to mess up his bathroom. Sam knew that Jim was a bit embarrassed about her, but at least he was getting some, and he thought he’d probably put up with the same to break the rather long spell of celibacy he was going through.

Sam had a quick shower and put on his fleece pyjamas as he just needed to feel comfortable. When he entered the living room Jim got up and handed him a super-sized glass of red-wine.

“You’ll need this!” He laughed, as they sat down to watch the early evening news.

“Is Jules coming over later?”

“No, we’ve split up.”

“What? Man, I don’t believe it. You should have said! I thought I’d had a shitty week!”

“Do I look bothered?”

Sam looked.

“Err, no, I guess not.”

“I ended it. She was a complete tramp and I know you know it too. I can do a lot better.”

“That’s true.” Sam replied, rapidly adding, “The bit about you being able to do better I mean. You can do a hell of a lot better.”

Jim laughed.

“Sam, frankly I don’t know how you put up with her being round here. She really was a fucking tramp! She was good at that I can’t deny, but it was going nowhere.”

“So why did you end it? Why now?”

“I’d had enough!”

“Sure, but there’s always a last straw.”

“Yes, I guess you’re right. I really wanted to go to this Halloween party that my old college were running for their alumni, and I thought she was fine with it. I’d even got matching costumes for us. Then she tells me she can’t face an evening with a load of my stuffy boring friends.”

“Oh!”

“Well I’m not proud of myself, but I let rip. Told her exactly what I thought. You know what, though, I feel 100% better now, really!”

They talked a bit more and drank a bit more. They eat the pizza and broke out the Scotch. Soon they were laughing to a late night talk show.

“Have you got plans for Halloween?” Jim asked, obviously reflecting on the days events.

“No, I’ve never been to one of those parties, but always wanted to. I quite like the idea of wearing fancy dress and I’ve never done it, not since I was a kid. I can see myself as a bit of a pirate, Johnny Depp!”

Jim laughed.

“Really? Well I’ve still got the tickets and don’t want to go on my own, we can get you a costume tomorrow if you’re interested.”

“Sure, why not? What are you going as?”

“I got this wizard costume. It’s really cool, deep blue with yellow stars on it and one of those pointed floppy hats. I’ve even got this big magic wand!”

“I bet you have!” Sam joked, but as he did their eyes met. They held their mutual gaze awkwardly for a few minutes before continuing their laughing, brushing off the fact that the double entendre had somehow changed the chemistry between them. “I’m not sure that a pirate and a wizard go together,” Sam added, “What was Jules going to wear?”

“I’d got a witches costume for her. She looked pretty hot in it to be honest and it wasn’t cheap either.”

Jim looked reflective. Sam could see that beyond his bravado he was upset at the break up. I guess you always hoped someone would change, but it was a sad fact that they never did.

“Hey man, sorry, didn’t want to stir that all up!”

“No problem mate. It’s just it is a really nice costume and I was really looking forward to the party!”

Sam really wanted to help Jim. He also realised that when he had said he wanted to be a pirate he had been lying. He couldn’t think of anything more amazing than dressing up as a sexy witch. He looked at Jim, their eyes both a little clouded after all the booze they had consumed.

“Look, I mean, this is not really me, but it’s Halloween, Rocky Horror Show and all that. I mean I want to do fancy dress, I might as well jump in the deep end. Jules was a similar size to me.”

“No mate, I ‘m not sure about that.”

“Why not?”

“It’s my old college party. They might think I’m gay?”

“And they won’t think you’re gay turning up with a Johnny Depp pirate? At least if I’m the witch you’re on the right side of gay.”

Sam could see Jim reflecting on what he had said and continued.

“I’ve watched Drag Race, I reckon I could scrub-up quite well. My mum always said I had lovely eyes and skin.”

“Wow! OK, I think you’ve blown my mind now and we haven’t even smoked anything!”

“Let’s sleep on it.”

To be honest neither of them slept that well. Sam was imagining being at the party as the witch and he found it quite erotic and had to keep relieving himself. Jim, on the other hand, was more concerned about whether it would work. If Sam could look like a girl, then it would be a brilliant evening. He’d be with a hot babe who he actually liked for the evening.

The next morning, slightly hung over, they met in the kitchen.

“Well?” said Jim.

“I’m still up for it, it wasn’t the booze talking.” Sam replied calmly.

“OK What’s the plan?” Jim asked, still not sure how it would actually work.

“I need to try on the costume and then if it fits, I’ll give Eileen at work a call. She knows a home visit beautician so she might be able to help with the make up and stuff, and a wig. You get the costume while I take a shower. Fingers crossed eh!”

When Sam emerged from his room wrapped in a towel he was pleased to see Jim in his wizard’s costume.

“Wow, you weren’t lying. That is amazing. Is it velvet?”

“Yes, I said the costumes weren’t cheap. Here’s the witches stuff, I mean all of it, there’s like panties and a bra too, so I mean it’s up to you how far you go.”

Sam felt his towel tenting at the thought and quickly gathered the clothes up before heading back into his room. He already knew he was going to be all-in.

He let the towel fall to the floor and picked up the white lace panties that had ruffled lace detailing. He held them to his face briefly and then bent down, slipping them up his legs. He noticed the hairs and was horrified. He would sort that out later.

He pulled them up felt a hot flush come over him. They felt divine, even if they looked odd with the end of his fully erect cock poking over the top. He put on the bra, fastening it first before sliding it round and slipping the straps over his shoulders. The feeling of the straps and material against his shoulders and chest did nothing to reduce his state of excitement.

He decided to forego the stockings for now, he just needed to see if the dress would fit. It was a beautiful black satin affair with scarlet piping details around the sleeves and hem. He was glad that he was skinny as it was quite tight waisted, the skirt flaring out to mid thigh length. He pulled it over his head. It went on OK, but he could barely reach the zip. Eventually after a few contortions he had done it up. He looked in the mirror. It not only felt amazing, it looked amazing, but there was no way he wanted Jim to see a man wearing the dress, so he took it off carefully, put on his pyjamas and went out into the living room.

The look of disappointment on Jim’s face almost made him want to cry.

“It doesn’t fit then!”

“It fits like a glove Jim, but I don’t want you to see me in it until the beautician has been round, so I need to sort that now.”

“Oh, OK, Wow!”

“There are two things I need you to do. I need you to exchange these shoes for a size eight and get me a bag to go with the dress.”

“Err, OK. So we are going then.”

“Yes Jim, I’m up for it as long as you are.”

“Cool!”

“And Jim.”

“Yes.”

“Don’t go to the shops in your wizard outfit!”

They both laughed.

Sam heard the front door close as Jim went out on his errand and was shaking as he got the details of the beautician and gave her a call. Just trying the underwear and dress on had made him realise that this was going to be an experience he would never forget and it needed to be done properly. He knew at once that this was his lucky day as she had had a cancellation and had a two hour slot available at 12:00pm. This was indeed providence! He explained that it was for a Halloween party, that he wanted to look as feminine as possible, and would need a wig, preferably very dark brown.

None of this was apparently a problem. His excitement was so infectious that as she lived locally she even offered to come round at 7:00 pm to quickly retouch things for him if he wanted. Oh yes he wanted. It was going to cost a lot, but she was going to leave him the make-up which he would need and the wig, because she would trim it to suit him.

Sam went back to his room. He only had an hour to get himself ready. He got in the shower, covered himself in shaving foam and got to work. He shaved his face super close before removing every hair he could find. He even trimmed his pubes, leaving just a landing strip. After he had washed the hair away he applied some lotion and looked at himself in the mirror. It was odd not having any body hair, but odd in a very nice way. His pyjamas felt completely different and so much sexier than they had before.

He put the kettle on and waited for the beautician. She was a few minutes late, but then Jim had not come back yet so that was fine. The beautician was lovely. She just told Sam to relax and let her get on with things. She tidied up his eye brows, attached false eyelashes and applied all sorts of lotions to his face. She shaved him even closer and put on some concealer before putting on the foundation. Contouring, blusher, then eyeshadow and eyeliner.

She explained everything as she did it and asked him to open and close his eyes as she worked. She took a lip lining pen and traced around his lips before applying the matching burgundy lipstick, making him squash his lips onto a tissue before applying it again with a brush. Finally she showed him the wig. It was a lovely bob style with a fringe which she explained would look good and be low maintenance. The fringe was perfect for that extra added femininity! Sam noticed it was very similar to her hair style, and that was clearly a good sign. Having fitted the wig she fussed around with it for a while, trimming it with scissors until she was happy. Finally she added false nails and painted his toe nails to match.

“OK darling, time you had a look. I think you’ll be pleased even though I say it myself.”

Sam got up from the chair and looked in the full length mirror. His pyjama’s for sure, but who the hell was that wearing them. He blinked. Looked again. Smiled. He absolutely loved this girl, and he loved the beautician too.

“Oh My God!” He eventually said, “that is unbelievable, thank you so much!”

“You are welcome darling, and to be honest, it was not that difficult, you have all the right features, the make-up just brings them out! We still have 20 minutes, so why don’t you put on your costume and get the real effect. I’ll make us a cup of tea. Oh, and here.”

The beautician fished in her bag and pulled out two breast forms.

“Use these in your bra darling, you can have them, they are an old pair I don’t use any more.”

Sam looked at the breasts, then at the beautician.

“Yes darling, I’m a boy too under all this. Now get changed, back in a moment.”

Sam pulled on the panties noticing that this time he was barely erect at all. He tucked his penis back into place before sliding up the barely-black hold-ups. He put on the bra and inserted the breast forms. Finally he slipped on the dress just as he heard the front door open. Jim was back. He heard the beautician and Jim talking and had just finished zipping himself up when there was a knock on his door.

“Decent?”

“Yes come in.”

The beautician entered carrying a pair of shoes. They were the strappy black sandals Jim had exchanged. She also had a bottle of perfume.

“Oh my! Don’t you just look lovely. Let me help you with these and then I’ll have to drink my tea and love you and leave you. I’ll be back at 7:00 like I promised!”

The beautician eased the sandals onto Sam’s feet. They were a nice two inch heel, sexy but not too hard to walk in. She gave Sam a squirt of the perfume too, explaining this was another present from the nice gentleman and then took his hand and led him to the bedroom door and into the kitchen where Jim was sitting reading a magazine with his tea.

He looked up and his jaw dropped so far and so fast it almost hit the table. He was silent, his eyes taking in the vision of beauty that he saw before him.

“It’s a bit rude to stare!” laughed the beautician, “but she is drop-dead gorgeous isn’t she.”

‘She’ though Sam, ‘drop-dead gorgeous’. He felt himself twirling slightly to show off and felt a twinge in his panties as his cock reacted to the situation.

“Errr, Ummm, Jeesus mate, is that really you? You are a total stunner, I mean like the lady said, you are off the scale!”

“It’s me Jim!” Sam said, speaking quietly and as femininely as he could. “I’m glad you like it!”

“Like it? I love it. Still not sure I believe it.”

The beautician was smiling as she drank her tea.

“Did you get me a bag Jim?” Sam asked in his girl voice.

“Err, yes, let me get it, and I got you a shawl in case it’s chilly.”

He brought the items back and approached Sam nervously, still unsure about the whole situation. You see he really really fancied Sam. For Sam it was similar. Jim had always been a great friend, but now he saw him differently. The sparkle in his eye as he looked at him was infectious.

“I love it Jim, ” Sam said, placing the bag over his shoulder and then wrapping the shawl around himself. It was so instinctive when he leant in to kiss Jim on the cheek, and he loved it when Jim went bright red.

The beautician’s smile beamed as she stood to go. “Well see you later Sabrina the Witch, seems like you’ve already cast your first spell!”

The rest of the afternoon Sam spent practising his voice and his walk until he was happy that it at least seemed natural and feminine. Jim was full of compliments and could not believe that he was taking this beautiful woman to the alumni do. Sam was way better looking than Jules, and Sam was a really nice person!

Suddenly it was 7:00 and the beautician reappeared darkening the eye make-up and styling the wig, setting it with some spray.

“There you go gorgeous. Does Sabrina have a kiss for me? Just to test the non-smear lipstick you understand!”

Sam laughed, and went to kiss the beautician’s cheek.

“Proper kiss I think.” She added, and their lips met, slowly, sensuously at first, and then their tongues were toying with each other as it became more passionate.

“Good, now look in the mirror babe.”

Sam looked, he was horrified his lips were all smudged.

“I’ll show you how to fix that,” the beautician said, handing him a tissue and lipstick. I’m sure you’ll be needing to do that a few times tonight!

The beautician left and Jim appeared in his costume. Sam looked absolutely radiant standing by the door.

“I think we need to practice a kiss if we don’t want to look too awkward.” Sam suggested. Jim was hypnotised and moved forward, their lips gently touching and pressing together.

“Good, that’s all for now or it will mess up my lippy.” Jim respectfully took Sam’s hand and Sam could not help seeing that he had worked his magic on Jim’s wand.

The car arrived at 7:30 and dropped them at the ball-room at 8:00. Sam suddenly felt completely out of his comfort zone, but Jim took his hand firmly and led him up the stairs.

It was the most fabulous evening. Sam had never had so much attention and he was sure that Jim was feeling both proud and jealous at the same time judging by the various looks on his face. Sam mixed with some other girls and talked about Jim as if he were his boyfriend. He enjoyed being with the girls, they were all so supportive and fun. The ladies room was a real revelation though as that was when their naughty side came out and he heard what some of them were planning for their dates later.

Sam danced with Jim, and with some other gentlemen that asked politely. He even danced round his handbag with some other girls to Dancing Queen as none of the boys seemed to like that song. By midnight Sam’s feet were killing him and he asked Jim if he would mind if they left. Jim was happy to oblige, he was so confused on every level bar one thing. That he absolutely loved Sam to bits.

Sam too had discovered that he had a new side, or perhaps rather she had a new side. Being a girl seemed so natural and made him feel so good it was like he had been born again. Sam sat close to Jim in the back of the car, placed a hand gently on Jim’s cheek and drew him into a kiss. It felt so heavenly that the next thing they knew the driver has pulled up outside their apartment.

They ran up the stairs, Sam’s heel’s clacking on the stone, and threw themselves through the front door. Jim grabbed Sam and went to kiss him, but Sam raised a finger and put it against Jim’s lips. He spoke slowly and sweetly.

“Jim, I know this has all just happened, but I want you to know that I absolutely love it and really want to go out with you again, like this, I mean, I want…”

Sam’s eyes watered and a tear began to slowly trace its way down to those beautiful lips that wanted the kiss so much.

“… I want to be your girl friend, I want to be your girl, I love it so much and I love you so much.”

Jim slowly pushed her hand away and pressed his lips to hers. She was his girl, she had been the moment he set eyes on her. Their kiss was both loving and intense and their passion for each other began to grow, Sam pressed against the door, Jim, strong and forceful.

Sam pushed him away, she needed more, and felt what she needed straining in Jim’s pants.

“I want your wand!” She said, slowly crouching down, her hands undoing his belt and zip before gently easing his throbbing red hot cock out from its unnatural confinement.

Jim groaned as she kissed and licked the tip, then ran her lips along each side, caressing his balls with her hand as she slowly and deliberately took him in. She loved the silky warmth of his throbbing cock in her mouth, she loved exploring it with her tongue and feeling it tickle the back of her throat.

She wrapped her hand around it and began to press and twist as she increased the pace of her bobbing, her tongue licking and her lips squeezing as she engulfed his love for her. She wanted to please him as much as he was pleasing her. She could hear from his moans that she was, and she started to moan too.

She began to taste him, a sweet beautiful taste. She felt a warmth start spreading through her body from her head to her groin, and suddenly, she heard Jim grunt, felt him push and as streams of cum filled her mouth, she felt those beautiful white panties she was wearing moisten as she shook from her own orgasm.