tagTranssexuals & CrossdressersThe Anniversary Present Day 05

The Anniversary Present Day 05


The Final Day

When Tom woke up Monday morning, Saffy was rummaging around in Tom's underwear drawer. He watched as she carefully ran through the choices and then settled on a pair of boy shorts. They were dusty pink in colour, made of a stretchy satin material with a ruched back and white lace edges.

She turned around with them in her hand and sat on the bed next to Tom.

"Wear these today," she said and kissed him. She dropped the underwear on the bed and went to the bathroom.

When she returned, Tom nipped into the bathroom for a quick shave and shower. Walking back into the bedroom, Saffy told him to put his panties on so that she could have a look. Tom did as asked and slipped them on in front of her. He turned around to show her the back and she ran her fingers over his cheeks, carefully pulling the material into his crack. Her hand drifted underneath and fluttered over his balls. She could feel his cock growing as she toyed with him.

Patting him affectionately on his bum, Saffy complimented him on how sexy he looked before getting dressed and ready for work. Tom wanted to make love but there was no time.

Once he was dressed he got the breakfast ready and they sat down together in the kitchen, making idle chit-chat.

When they were clearing the dishes, Saffy made an announcement.

"I've another surprise for you tonight so don't be late, ok?"

"Sounds interesting," Tom beamed. "What sort of surprise?"

"Never you mind. Just make sure you are home by 6 o'clock."

After a brief goodbye, Tom and Saffy made their separate ways to work.

Tom emailed Saffy several times during the day, playfully trying to get some clues about the surprise in store. He was sure it was going to be sexy and his cock twitched whenever he thought about it. Saffy declined to give him any clues and told him to wait.

Wait, he did. Another gruellingly long day at the office but at least he got away on time and was home at 6.

Saffy was cooking when Tom walked in. He kissed her and looked at her expectantly but she didn't mention his surprise.

"You go and have a shower and get changed and I'll give you a shout when the meal's ready. I've put some clothes on the bed for you to wear."

Tom was excited by this – maybe his surprise was a new outfit of some kind. He nipped up stairs and went straight to the bedroom. On the bed he saw a cream satin blouse, a short black pencil skirt, a pair of silk stockings, black satin panties, a matching garter belt, waist cincher and a black bra. On the dressing table he saw a blonde shoulder length wig and some make-up.

He gulped as he realised what Saffy was planning for him; a total feminisation.

He stripped off and jumped in the bath. He shaved his body and washed quickly before returning to the bedroom. His stiff cock throbbed with anticipation as he started to dress.

He was almost dressed when Saffy walked in.

"Dinner will be ready in about 20 minutes," she smiled. "Sit at the dressing table and I'll do your make-up."

As Tom watched, Saffy carefully applied his make-up. Gradually his male features softened and all but disappeared from his face. Finally, Saffy put his wig on his head and the transformation was complete.

Tom stood up and looked at himself in the mirror. He admired his feminine appearance and thanked Saffy for his surprise. She smiled back at him and kissed his deep red lips very lightly.

During their meal, Tom and Saffy talked as if it was just another meal and nothing unusual was happening. Every now and then, Tom would touch himself; stroke his skin through his delicious female clothing. His body felt like one enormous erogenous zone. His cock was straining inside his delicious soft satin panties and crying out for attention but would have to wait until Saffy was ready.

After dinner, Saffy took Tom back upstairs. She touched up his make-up and then laid him on the bed. She grabbed some scarves from a drawer and tied Tom to the bed. Once he was ready she blindfolded him and kissed him.

"I'll be back in a minute," she whispered and left the room.

She had been gone ages. Tom was getting a little concerned and called her name out. He heard her faint reply from somewhere downstairs and a few minutes later she was back in the bedroom. He felt her hands touching him, running over his face and down his body through his blouse, which she slowly unbuttoned before kissing his chest.

Then he felt her hands roaming all over his skirt, sliding down his stockinged calves to his feet and back up to his waist. He squirmed and wriggled with excitement as she removed his skirt; her hands gliding over his crotch and between is thighs.

Her mouth moved over his bulge, her tongue licking at the tip of his cock through his delicate satin panties. He felt her hot breath as she engulfed one ball and then the other. As she returned to his throbbing cock, a teardrop seeped through his panties and she licked and sucked it into her mouth.

"I wish I could watch you," he pleaded.

"Shh," was her only reply.

Tom felt his cock gently pulled from his panties and then Saffy's mouth plunged down onto him, sucking him hard and taking him deep into her mouth. He groaned in ecstasy and ground his manhood into her.

"How are you enjoying yourself so far?" Saffy breathed in Tom's ear. Tom was suddenly confused and his body went rigid as he said "I... I don't understand." It was all he could say.

"I told you it was a special surprise tonight. The mouth around your cock belongs to a lovely woman called Cherry. Say 'Hi' to Tom, Cherry."

Cherry stopped sucking his cock for long enough to say 'Hi Tom' and then carried on.

"Cherry's a transvestite, Tom. And a very cute one too. Tonight, I want you to pamper Cherry, to suck her and let her fuck you. You don't have to like it, it's up to you but I want you to do this for me. If you don't enjoy it, then it'll never happen again but I want to watch you with her this once. Ok?"

Tom's faced was hard to read, especially with a blindfold on so Saffy carefully removed it. She was none the wiser. Tom stared at her briefly and then looked down at Cherry.

"Look at me." He said to Cherry.

Cherry looked up and waved a little wave before going back down on him. She let out a murmur of pleasure as she did so.

What little he saw of Cherry's face was enough for him to see she was indeed quite pretty but the dilemma of what Saffy wanted him to do was troubling him. He rested his head back on the pillow and acknowledged that he was enjoying a really great blowjob even if it was from another guy. But then he thought about what her cock would look like inside her panties, a shimmering bulge much like his own, he supposed. Fuck it, he thought, if this is what Saffy wants then that's what she'll get.

"Untie my hands, darling." He said to Saffy. "It's okay, I want to play."

Saffy loosened Tom's restraints and he sat up and looked down at Cherry again. He leaned forward and encouraged her to come closer.

She half-stood for a moment and then slid up the bed until her face was just inches away from Tom's.

"What would you like me to do?" Tom asked.

Cherry looked deep into his eyes and said, "I'd like you to take a closer look between my legs."

Tom's hands shimmied down Cherry's back and rested on her pantied buttocks. He gently encouraged her forwards until she was kneeling on either side of his chest, her bulge almost touching Tom's lips.

Tom moved away by just an inch or two so that he could look at her better. She was wearing nearly black and faintly see-thru panties. Her cock was soft and pointing at three o'clock.

Surprised by how he felt, Tom realised he really liked what he saw. Her lightly bronzed skin and feminine attitude was sexy and inviting. But her bulge was one of the sexiest sights he had ever seen. Taking a deep breath, Tom pulled Cherry to him so that her shimmering profile touched his mouth. He could smell her perfume mixed with pheromones and he suddenly felt intoxicated by it.

Cherry pushed herself onto Tom's mouth and then gently ground herself on his face, moving in circular motions. Tom could feel Cherry's cock growing and soon he found himself kissing and licking at her eagerly, his lips and tongue searching out every inch of Cherry's prick.

Moving his hands round to Cherry's lap, he fondled her through her panties in much the way he had done to himself so many times over the last five days. His fingertips lightly traced every inch of her cock and balls and he slid one finger over her perineum and firmly against her hole.

Tom pulled her cock out of the top of her panties. He started tentatively, kissing and licking her erection, and then Cherry pushed her hips back until her cock was at the right angle to enter Tom's mouth. He took her in without pausing and Saffy, who was sitting naked on a chair beside the bed, took great delight in hearing him groan with pleasure as Cherry's long, thick cock began gliding in and out of his accommodating mouth.

As Saffy watched, she gently stroked her clit and saw that Tom's cock was stiff and throbbing. She had thought he might go along with this unwillingly but she had never imagined how much pleasure it would give him. Strangely, his excitement increased hers and Saffy found this fantasy was unfolding in a way she had never expected.

Cherry slowly fucked Tom's mouth for a long time, enjoying both the sensation and the pleasure it was giving this adventurous couple. Some jobs were better than others and she suspected this was going to be a good one.

Pulling away from Tom, Cherry looked at Saffy and nodded. Saffy took the queue she had been waiting for and grabbed a bottle of lube from the bedside table. Cherry told Tom to roll over, which he did without question. He knew what was coming and silently prayed it wouldn't be too painful.

Cherry leaned forward and whispered in Tom's ear. "Don't worry, I'll be very gentle."

Saffy pulled Tom's panties down to his thighs and worked a lubricated finger into him. Cherry slipped on a condom and lifted Tom's hips to slip a pillow under him. Tom's breathe was coming hard and fast as his excitement grew. When Saffy had finished lubricating him, Cherry lay down on top of Tom, her weight holding him down and making him feel incredibly submissive.

He felt the tip of her cock at his entrance and she held it in place, pressing very slowly but persistently against his tight ring. Gradually, she pushed in an inch and then another before pulling back out. She resisted the urge to force her way in and shallow-fucked Tom for a while, letting his stretched hole get used to the invasion.

Before Tom had fully appreciated it, Cherry had squeezed passed his sphincter and was a good four inches into him. She took her hand away and started pressing further into him until finally, all eight inches were buried in him. With her weight still holding him down, Tom was powerless to resist as her cock slowly probed him. She held still for a moment and carefully pulled Tom's hips back, signalling him to kneel.

When they were both kneeling, Cherry told Tom to take control and he started to move back and forth against Cherry's cock, slowly at first and then faster as the sensation moved from discomfort to pleasure.

Saffy was breathing heavily and fingering herself as she watched the transformation in her husband. The sight of Tom impaled by Cherry was both intensely sexual and extremely sensual. Saffy climbed onto the bed and took Tom's semi-erect but dripping cock in her mouth.

Tom and Cherry were in synch, both pushing against each other as the pace quickened. Cherry was pounding into Tom now and he was crying out in pleasure. He was feeling every inch of her long cock pounding into him, a relentless assault on his submissive body. With Saffy's mouth around his cock and the sensations in his hole being so intense, he felt dizzy.

Cherry was moments away from cumming when she stopped. Pulling carefully out of Tom, she quickly stepped to the side of the bed and ripping the condom off, plunged her cock back into Tom's mouth.

Saffy stopped sucking Tom's cock and watched as Cherry held Tom's mouth and slammed her cock in and out. Tom was taken by surprise as Cherry's orgasm exploded in his mouth, hot cum shooting down his throat and dribbling from his lips. As Cherry's climax passed, she squeezed her cock to make sure every last drop of cum emptied into Tom's mouth.

Tom barely had time to catch his breath before Saffy told him to lie on his back. His face still sticky with Cherry's cum, Saffy climbed on his face and rode his mouth to her own orgasm. She was like a wild woman, thrashing and grinding against his mouth, crying out as her climax exploded from her body.

Saffy climbed off the bed and looked down at Tom. She kissed him lovingly and whispered, "It's your turn now", with a knowing grin.

Tom lay down on his back and Cherry grabbed the lube and coated two fingers in it. Saffy removed Tom's panties and wrapped them around his aching cock. She began to stroke him gently as Cherry pushed two fingers inside him. She curled her fingers upwards until her tips were pressing firmly against his prostate. She stroked and massaged the gland as Saffy held Tom's cock and watched the clear sticky fluid seep from his cock in a steady flow.

Tom was groaning as Cherry's fingers worked their magic on him. He'd never felt this before and it was wonderful. He began to groan loudly as the massage increased in intensity. Sensing he was about to cum, Saffy took his panty-clad cock into her mouth and sucked hard, drinking in the pre-cum that leaked through his panties. Cherry also sensed he was about to cum and timed her strokes to the spasms she felt in his sphincter.

Tom's eyes watered as he felt the longest and most intense orgasm of his life burst into his panties and his wife's mouth. Saffy sucked and cooed as the hot semen seeped through the thin satin material and onto her tongue.

Time seemed to stand still for Tom as every fibre in his body screamed in pleasure. As he began to come round again, he heard Cherry say "Is there anything else I can do for you?"

"Please, fuck me again." He heard himself say...

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