Chapter 2: Let’s Make Up
Lynn walked into the bedroom and threw the bags down on the bed, a white lacy suspender belt falling out from one of them.
“Wow” smiled Chris, “you weren’t kidding about the weekend.”
“I certainly wasn’t. Now lose the dressing gown and turn around. Shut your eyes too, keep them shut until I say otherwise, and remember, no more questions.”
Chris did as he was told. He really wished he could watch her undress and put on that new lingerie.
He heard her pull off her dress and he thought he heard her slip into some high heels too. His brain, or was it his cock, was telling him this was almost as good as watching.
Suddenly he felt her warm naked arms around his waist, then he felt some stiff material pressing against his stomach, then it was pulled tight at the back, Lynn fumbled with the clasps, Chris felt the straps gently tickling his legs. He wanted to challenge her, this wasn’t right! It wasn’t what he was expecting at all, but his hardening cock was saying something completely different.
“Keep your eyes closed, I’ll help you to the bed.” She gently steered him backwards until his calves were stopped in their tracks and he slumped down onto the mattress. Lynn lifted his right foot and slipped the tight nylon stocking onto it, working it slowly up his leg to his thigh.
“That’s it gorgeous, you just relax and enjoy it! It’s a good job you have pretty hairless legs, but we can perfect that later”. She did the same with the left leg, Chris kept his eyes closed. He said nothing. The sensations he was feeling were driving him mad.
She pulled some stretchy material over his head and guided his arms through the straps, pulling the material down to his waist. She ran her hands over his chest and then rubbed her fingers slowly over his nipples through the material, making him let out a sigh and shiver.
“Stand up honey.” She said in a tone that asked rather than ordered, but he obeyed none the less. He felt her pull the stockings up and attach the straps of the suspender belt, adjusting them so they pulled tight and pressed against his thighs. It felt divine, and his cock, which was now standing to attention was throbbing.
“Now then, that isn’t very lady like is it!” Lynn said, grabbing his cock, gently twisting and pulling it while putting a finger over his mouth for silence. “How on earth will I get your panties on? I’d better take a closer look and see what I can do about it.”
While continuing to give him a slow hand job, she nibbled his ear lobe, slid her mouth down to his nipples and gently bit and licked each one through the silky vest. He felt her move one hand to cup and caress his balls, using the thumb from the other to rub his left nipple. As she moved down on him, he felt her long hair tickling his glans, soon replaced by her warm breath. She lowered her hands and placed them on his nylon covered ankles while slowly engulfing the end of his cock in her mouth. Running her hands slowly up to the backs of his knees, she swirled her tongue around the sensitive underside of his cock, while gently sucking and rubbing her moist lips over the upper ridge again and again.
Chris’s legs were trembling uncontrollably as she gently stroked them, his brain was on fire, hardly able to handle the flood of new and exciting sensations that were tormenting him. Then he felt it in his balls, he felt his impossibly hard cock momentarily get even harder. Lynn pushed her head forward until her nose and forehead pressed against his stomach, expertly and easily taking in his entire length. With the tip of his cock encased in her throat, she gently pushed against him in short sharp movements until the friction from the tightness of her throat caused him to explode, crying out in ecstasy as Lynn pulled back and kept sucking, savouring every last drop of his cum, and swallowing it greedily.
When she had finished licking and cleaning his gradually deflating member she pushed him back. He stumbled and fell on the bed helplessly. Leaning over him she told him to open his eyes and then, staring into them, she kissed his lips, forcing her tongue between them, a deep wet kiss and his second taste of cum that day.
Pulling back and seeing his cock was finally flaccid, she spoke gently. “Well I think you enjoyed that didn’t you Chrissy, now let’s finish getting you dressed.”
“That’s was amazing Lynn, I’ve never felt…”
“Shhhh sweetie, now we’ve got that thing of yours out of the way, let’s get these on before it recovers. Now, lift up your legs.”
Producing a pair of white satin and lace panties from a bag, she pulled them up to his knees.
“Lift your bottom up, lover.”
He felt the panties wrap around his thighs. She tucked his cock between his legs and brought his own hand down to rub across the front. He couldn’t believe just how amazing the smooth satin material felt and the amazing sensations it generated as he rubbed up and down.
“Naughty! No playing with yourself. Now, stand up and go look in the mirror.”
Chris stood up and walked over to the full length mirror on the wall. He felt the slight abrasion as the nylon on his legs rubbed together. He loved the constriction of his cock in the smooth warm satin. The white vest straps felt like they were caressing his shoulders and the tight material hugged his chest. Best of all was the feeling of the suspenders tight against his thighs, stretching and teasing as he walked.
Fortunately Chris was in reasonable shape, neither fat, nor too muscular either, so as he looked in the mirror he was quite surprised and somewhat taken aback by effect the underwear had on his appearance.
“Hey! Stop admiring yourself and put these on” Lynn said. He could see her approaching him in the mirror carrying a pair of white strappy sandals with block heels. “Let me help you with them.”
She knelt down in front of him and placed his feet in each sandal and buckled them up.
“They’re three inch ones honey, high enough to make a difference, but not too hard to walk in after a bit of practice. Try it!” Encouraged Lynn, “I’ll hold your hand to steady you.”
He took his first faltering steps. He noticed the extra height and the way it made the muscles in his legs feel different. “Keep your shoulders back and take smaller steps than you usually would. Walk over to the dressing table and sit down”.
He looked in the mirror again.
“Well?” Asked Lynn. “What do you think? How do you feel?”
“It’s hard to say. I can’t believe how amazing this stuff feels on me, I love the look of my legs! It’s a shame I’m just a bloke in women’s underwear really!”
“Yes, I agree. From the neck down not bad at all, so how about a bit of makeup to fix that?”
“Makeup? Err. Not sure about that I mean isn’t that going too far?”
“Chris, you’ve gone this far and loved it! Why not go the whole way and see how you feel? Look here, try this on.” She opened another bag and took out a box. In it was a medium length dark blonde wig. She brought it over to him as he looked at it mesmerised. She lifted it up to his head.
“Look at me… now lean forward… there you go.”
She had pulled the wig on over his head and he was now looking at a not unattractive blonde woman having her hair brushed out. He could not believe how much the wig changed his appearance.
“Well? What do you think?” Queried Lynn, playing around with the fringe. “A bit of makeup will soften your face and finish things off.”
“Is this from the theatre?”
“Yes, I picked it up on the way back from the shops along with my make-up kit, they won’t miss it, it’s far too on-trend for anything they are doing at the moment. Any case, you still haven’t answered my question?”
“OK, yes, do it, please. I’m sort of intrigued to what I end up looking like, and see just how good you are at your job I suppose!” He laughed, “how long will it take?”
“Let’s say an hour for a proper job. I’ll need to tidy up your brows and stuff, but not in a way anyone would notice. You go and get yourself a really close shave and I’ll get ready here. Remember to shave super smooth, in both directions, and put on some lotion on when you’ve finished. I’ll hold on to the wig.”
He stumbled off to the bathroom having initially forgotten about his heels and then finding the whole posture thing a bit strange. When he came back, Lynn was ready.
She got to work. Primer; concealer; foundation. Then some different shades of powder to shade his face, remove some of the shine and add some blush to his cheeks. She explained what she was doing as she went along, but he could not see the results as she would not let him look in the mirror.
Eye shadow, some false eyelashes, eyeliner, contouring, then a final bit of trimming and pencilling on the eyebrows to get a nice arched shape. Finally she worked round his lips with a lip pencil, exaggerating their size before finally applying some deep red lipstick. She took her time, and got him to blot his lips onto a tissue a couple of times. She put her finger in his mouth, “Press your lips hard around my finger while I pull it out, it will stop you getting lipstick on your teeth”. One more application, some lip gloss and finally a fixer spray.
“Done! Now let’s put the wig back on. OK. Ready?”
“I guess so. My face feels a bit weird.”
She turned him round to face the mirror. For the second time today he was stunned into silence. He had to blink and move his head slowly from side to side to prove it was actually him. She was absolutely gorgeous, he would have never imagined it was possible. Lynn brushed out the wig and applied a little hair spray to hold the style in place.
Chris continued to look in the mirror, spell-bound by his own reflection.
Lynn appeared behind him again.
“OK sweetheart, one last thing, stand up and put this on.” She was holding up a mid-length skater dress in navy blue with a white floral pattern. He stood up and stepped into it while she held it for him. She zipped it up and produced one of her pearl necklaces, fastening it at the back of his neck.
“Bit flat chested, but you’ll do”, Lynn laughed, “Goodness, it’s one o’clock already, why don’t you go make a bit of lunch while I tidy up here and change.
“OK, I’ll get changed too, are you going to remove the makeup, I’m not sure I would be able to get it all off.”
“Oh I don’t think so, not after I’ve been to all that effort. You can stay dressed for me can’t you. I thought you we could try some more new things this afternoon, but we do need to eat and I presume you can fix me lunch whatever your wearing!”
Lynn put her arms around him and gave him a tender kiss on the lips, looked into Chris’s eyes, lingering slightly before moving her gaze to his mouth. She kissed him more passionately, and he felt a hand running up the front of his leg under the dress, past the stocking tops, until it was squeezing his cock through the panties, her touch across the nylon and through the satin was simply electrifying!
He returned the kiss, and made a move on her, but she pulled back, squeezing his cock a bit harder, “Uh, uh! We can’t mess up the rest of the makeup. Here fix up that smudged lippy in the bathroom on your way downstairs, removing her hand and passing him a tissue and the lipstick.
Chris could feel his cock trying to burst out of the panties which, together with tightness and the tuck were doing a great job of keeping it in place. He couldn’t help thinking that Lynn could be very persuasive, or perhaps this was exactly what he had always wanted and she knew it! He certainly wasn’t complaining! He felt amazing.
He was a bit awkward walking down the stairs, and had to clutch the bannister, but was much more comfortable in the kitchen, listening to the clacking sound of his feet on the tiles as he wandered from fridge to sink to work surface preparing a salad, even wearing Lynn’s apron to protect his dress from any splashes.
He was just finishing off when the doorbell rang. He froze in horror, fantastic as he felt, there was no way anyone could see him dressed like this!
Mercifully Lynn called down that she would get it and he heard her open the door. He listened to the conversation, his heart racing until he realised it was just a grocery delivery and incredibly relieved he relaxed, placing the bowls on the kitchen table and going over to get the cutlery out.
Lynn was still on the door step and it seemed there was something wrong with the order. Still listening, he could make out that the driver had located the missing items. “Sorry Mam, it was right at the back of the van because it’s so heavy, let me take it through to the kitchen for you.”
Chris froze, there was nowhere to go, apart from the back door and into the garden and he had to decide now. Unfortunately the garden was overlooked by some flats, and that was enough to sway him to stay in the kitchen, after all this guy was only dropping a bag. He turned to face the sink and began to look busy.
“It’s through there,” he heard, “my friend Christine is in there, say hi, but she has a dreadful sore throat at the moment so she probably won’t say anything. Chrissy, it’s the delivery guy just needs to put this in the kitchen, it’s too heavy for me to lift.”
Chris turned his head round and pulled out the best smile he could in the circumstances, looking straight back at the good looking young guy. Despite his fear, he was intrigued to know if the delivery man would be able to tell, and more importantly, how he would react.
“Afternoon Mam”, he smiled back, “hope you feel better soon.” He bent down to place the bag on the floor by the door.
Chris whispered horsely, “Thank you.”
“Bye, nice to have met you and maybe see you around.”
Chris heard a muffled conversation and then the front door close. Lynn came in laughing carrying a couple of bags which she also popped down by the door. She was looking very nice in short ditsy body-con dress which was making the most of her long legs.
Chris challenged her, “Oh yes very funny, but I guess I should at least thank you for the sore throat ruse, that was a bit of a life saver.”
“Ha ha, I wasn’t laughing about that! No, as he left he said you were really cute and asked me if you were single. Ha ha, not sure which is funnier, his cheeky request or the surprise he would have got!”
“Very funny. You’re just making that up! honestly Lynn!” However, he had already felt his cheeks redden and his cock twitch. This feeling was the best ever, but he didn’t want to give too much away to Lynn. His mind was in turmoil as it really felt so much more than just a sexy game. He was feeling things he had never felt before, and he was beginning to really want to feel like a woman.
Lynn continued: “Seriously he did, here’s his card! I saw you blush when I said it! I’m sure that you flashing your stocking tops at him was a massive turn-on!”
“What… no way… was I?”
“You certainly were, still are actually when you bend over! It’s not easy being a modest woman when you’re dressed like a tart!”
Chris looked down and realised that his stockings absolutely did need pulling up!
“Well, yes, but I wasn’t blushing!” he countered, blushing.
“You just so were, and you just so are! Don’t worry it suits you, makes you look even more cute! So what do you say about my make-up skills now eh! Aren’t I just the best?”
That was clearly a rhetorical question, so Chris did not reply, just raised his eyebrows and nodded. Having noticed the salad, Lynn let him off the hook.
“The salad looks nice. Let’s put the groceries away and discuss plans for this afternoon while we eat. You are just such a sweetheart!” She kissed him on the cheek, squeezed his ass, bent down and pulled up his stockings and adjusted the suspender straps.
A few minutes later they were sat opposite each other at the kitchen table eating the salad. Chris was very conscious of the lipstick as he ate so instead of his normal technique of almost bolting his food, he took little bites in a much more ladylike fashion so as to hopefully not smudge or remove it.
Sipping on his orange juice he was pleasantly surprised to feel a stockinged foot sliding up under his dress and along his inner thigh until the toes touched the panties encasing his cock. Lynn has finished eating before him for once and was now tapping away on her phone as well as playing footsie under the table. She looked up and smiled at him through her lashes.
“That’s nice, don’t stop”, he purred.
“I see, are you ready to try something else? A bit of role play perhaps? How about this? You are Chrissy my friend and I’m a lesbian who fancies you like crazy. You have never made out with another girl, but you aren’t adverse to the idea. It’s my job to seduce you and your job to put up a bit of resistance. What do you think?”
“Mmm, OK, can’t say I’d object to that, sounds like fun!”
“Right, well you’ll need to act all shy and girly, and you can use this opportunity to practice your voice. Try speaking from the front of your mouth, not from your throat, and don’t worry about the pitch as a deeper voice is sexy. So come on, the more believable your voice is the naughtier I’ll be. Shall we start?”
Chris thought this sounded like an amazing idea and jumped into the role straight away.
When Lynn rubbed her foot on his leg, he looked up quizzically and Lynn apologised, saying she had a bit of a cramp in her leg and has to stretch it out.
Chris tried speaking: “No problem Lynn, you just stretch out when you need to. I love your dress by the way.”
Lynn’s advice worked well. His voice sounded softer, but he it took him a while to get the discipline to keep it from moving to the back of his throat and spoiling the effect. Lynn replied.
“Thank you Chrissy, it’s one of my favourites. You don’t think it’s too short?”
“Not at all, you have the loveliest legs, you should show them off more often.”
The conversation continued, Chris feeling more confident all the time, and then Lynn’s foot stretched out again and brushed up his leg, but this time it lingered on his thigh, making a short back and forth motion as her toes curled.
“Oh, sorry, there I go again, let me move, this cramp is driving me mad!”
“Don’t be silly, it’s not bothering me at all, you stay put”.
“You’re such a darling, but let’s take these coffees into the front room where I can stretch out more easily.”
They sat next to each other and Lynn stretched her leg again and sighed.
“Where does it hurt?” Asked Chris in his best girl’s voice yet, “let me take a look, maybe I can give it a rub.”
“Would you, it’s at the back of my left thigh”, let me stand up. Lynn turned away from him and hitched her dress up slightly, revealing the top of her tights.
Chris leant down and placed his hands just above her knee, then moved them up applying a gentle but firm pressure.
“Does that hurt?”
“No, it seems fine, try a bit higher.”
He moved up.
“I don’t want to ruin your tights, do you want to take them off?”
“Oh yes, if you don’t mind continuing! You’ve certainly hit the spot I can feel it already! Perhaps you could apply a bit more pressure. Actually, would you mind if I lay on the floor while you do it.”
“Not at all, here, lie on this rug.”
“OK. Let me take these tights and this dress off, I don’t want to crumple it. You’ve got magic hands for sure!”
Chris’ voice maintained its feminine purr while he feigned embarrassment and averted his gaze as Lynn let the dress fall to the floor before pulling down her tights leaving her standing in just her bra and panties.
Once she had made herself comfortable on the sheepskin rug, Chris massaged the very tops of her thighs, his hands “accidentally” brushing against her panties several times. Eventually Lynn let out a sigh and asked if he would do the front of her thighs too. Naturally he agreed, his own panties straining to retain his ever hardening cock especially as he could sense the subtle smell of her excitement.
He repeated the massage, his thumbs running up either side of the panties, brushing the outsides of her vaginal lips which were radiating warmth, the material getting damper after every stroke her arousal becoming more obvious all the time, her musky smell filling his lungs as he took a deep breath.
To spur things on Lynn regaled a story of how his touches reminded her of a time she had almost orgasmed during a massage at a Spa and Chris felt more than obliged to give her a repeat of that experience. He looked deep into her eyes and began to bring her to the most wonderful climax, her body shaking as she groaned.
She said how much better she felt and asked if she could reciprocate with a shoulder rub. Chris was somewhat hesitant as he played his part, but eventually agreed after Lynn simply wouldn’t take no for an answer.
Lynn suggested they move back to the kitchen as the chairs there were more appropriate for the shoulder rub, but did not put her dress back on.
“Here, Chrissy, let me slip the dress off your shoulders.”
This time Chris made the right move.” Actually I think it would be better if I also took it off, I don’t want to spoil it.”
“Of course, let me unzip you, ooh, what lovely panties! Now sit down, and just move your knees apart so I can stand in front of you if I need to, I’m just going to slip your vest straps down”.
Lynn had moved the chair to the centre of the kitchen and put a towel on it. After putting some hand cream on her hands she moved behind Chris and began the firm strokes either side of his neck stretching round until she had pushed the vest right down and was rubbing Chris’ nipples. Chris sighed appreciatively and rolled his head back, the touch of his own hair on his back, and the teasing of his nipples, sending him off into a sublime trance.
Lynn moved to the front. While holding and rubbing Chris’ shoulders, she pulled him forwards so she could reach down his spine until his nose was touching the top of her breasts.
Lynn’s hands were now on the side of his chest, her thumbs gently rubbing Chris’ nipples as she steadied herself so she could set one of her knees brushing against his now painfully constrained erection.
Chris could take it no more, the game was over. He had been seduced by the master, or was it the mistress? He raised his hands and ran his thumb along the outline of her sex causing her to thrust her pussy towards him. Resting his forehead on her taught stomach, he tugged down her panties and savoured her taste on his lips, inserting his thumb as far as it would go, swirling his tongue around her clitoris, flicking and licking as he felt her body tense and relax, thumb moving in and out, always responding to her breathing and sighs.
Lynn’s knees buckled and she grabbed his shoulders hard as her second orgasm flowed through her body. When she had composed herself, she leant forward, kissing him hard and furiously while her hand slid down the front of his panties pulling out his full length with some difficulty. Stepping out of her own panties, which pooled delicately on the floor, she proceeded to drop down on him, guiding him in with her hand and sitting on his lap. Rocking backwards and forwards, squeezing and twisting, thrusting, withdrawing, all the time continuing to devour his mouth with her own.
Throwing their heads back, they climaxed together in a crescendo of groans that must have been heard in the next village. Staying in position, they continued to kiss as Chris’s cock gradually softened and he could feel the cum running out onto his legs.
They just sat like that for a while, before Lynn slipped off and, calmly, suggested that a post coital coffee might be nice, which they drank still dressed, or undressed, as they were.
“I thought we were meant to be doing lesbian seduction”, Chris asked pointedly.
“Yes, well, it was mostly that until I just had to have that big salami you were packing in your girly lunch box”, Lynn chuckled and so did Chris. “I’ve ordered a few interesting things on-line which should be here tomorrow morning”, Lynn said, “You can go back to being Chris if you want, your make-up is pretty much all over the place after that, so needs redoing anyway. I’ll help you clean-up and while we are doing that we can get on and make a plan for the evening. Who will you be later Chris or Chrissy?”
“Judging on today so far, I think you can probably answer that yourself!” Chris grinned, relishing the thought!