Jim almost swooned from the experience. Touching the red silk panties was exciting but when Philip began to pull them up over Jim's smooth thighs, the feeling was incredible. Jim knew he was slipping down into the delightfully erotic state of being submissive and feminine and found himself welcoming it with every part of his being.
Teddy had driven Jim over to Philip's house. Along the way he asked Jim how he felt about what happened the night before. Teddy didn't let Jim get away with flippant answers. He probed and prodded him with questions. Jim felt it best to give him the answer exactly as it popped in his mind.
"Did you notice that Philip was wearing lipstick?'
"Yes, I liked that."
"Did it make Philip more attractive to you?"
"Yes it did. I think he had lipstick on his nipples too, didn't he?"
"Did that excite you? Would you like Philip to make you more exciting?"
"Yes. I find it incredibly sexy."
The questions continued and there was no doubt in Jim's mind what Teddy and Philip had in mind for him. He admitted to Teddy that Philip's feminine demeanor made him hard. Yes, he had thought of himself in a feminine role. Yes, he had pictured himself wearing women's clothes.especially frilly lingerie. Yes, he did like the feel of silk.
"What about satin? Do you like satin, Jim?"
"Yes. Satin feels so smooth."
"And what about lace? Do you think you'd look good in lacy things?"
"Oh yes, lacy things are very sexy. I'd like to wear lace, too."
"And what else?"
"I like it all. Silk, satin and lace. I'd like it all!"
Jim could feel his cock hardening as he talked to Teddy about all these wonderful intimate things. Teddy chuckled a bit and told him that he was delightful and that he and Philip had exciting things planned for him.
Before Jim could ask for more details, Teddy pulled up in front of a very modern looking home overlooking the ocean. Turning towards Jim, Teddy told him that he would be back in a few hours. He leaned over and kissed Jim tenderly on the mouth for a few seconds.
"I'm excited thinking about you, Jim. Have a good time. See you soon."
Jim walked to the house and was about to ring the bell when the door opened seemly on its own. A young black man that Jim instantly recognized from the night before, Ralphie opened the door. How could he forget the first cock he had ever sucked!
Walking in Jim glanced to his left and saw Philip standing inside a large sunken living room, wearing a long sheer black negligee. In spite of his large size, or maybe because of it, Philip looked magnificent!
"Come in, Jim. We've been looking forward to your visit."
"Philip, you look magnificent!"
Jim walked over and Philip opened his arms and welcomed Jim, his arms holding him lightly but firmly against his negligee clad body. Without hesitation Jim's hands held Philip's arms around him. Jim knew his place; Philip was his male lover and he was submissive to him. He loved it. Their lips met and Jim again knew the feeling of being loved and wanted and desired.
Instantly Jim's mouth opened and he experienced the warm lips drawing him in and the luscious tongue dancing in his mouth. Mmm.
After a long knee-softening kiss, Philip drew back slightly. "You know, Ralphie, I believe."
Still in Philip's arms, Jim turned and greeted Ralphie with a smile.
"Yep, I sure do, and I know why!" he explained.
Ralphie had on a short dark green kimono that showed off his long thin legs. He was grinning but held back from moving into the room with them.
"Ralphie works occasionally.under me," Philip chuckled. "Don't you, Ralphie."
"I enjoy working UNDER you, Philip," Ralphie said, emphasizing the word.
Turning back to Jim, Philip said he wanted to show Jim around. As they toured the home, Jim found it was virtually a mansion. Philip held Jim's hand and took him from one room to another. The ocean view was like a post card and was visible from most rooms. As Philip led Jim up the stairs one hand held his and the other softly caressed his body. Half way up, Philip stopped and kissed Jim again. It was a soul-searching kiss that made Jim moan softly from its passion.
At the top of the stairs Philip led him into his master bedroom. A full assortment of red ladies lingerie was laid out on the huge bed. It looked like a Frederick's of Hollywood catalog.
"Guess who these are for?" Philip asked. "But first I imagine you'd like to take a nice bath. Ralphie's here to help you, darling."
Jim nodded. He liked being called 'darling'.
Philip held his hand and pulled him close. Kissing Jim again, his hands reached down and fondled his now hard cock. Jim stood still, enjoying the attention.
"Okay, Ralphie, please help Jim with his bath, will you, honey?"
Ralphie went into the nearby bathroom, Jim following. The bath was a huge sunken tub and was already filled with fragrant billows of suds. Ralphie began to slowly remove all of Jim's clothes. As he knelt to take off Jim's shorts, he kissed the head of Jim's hard cock.
"Tha's all I can do right now. Philip's orders."
After Jim was naked Ralphie removed his kimono. Under it he had on a pair of dark green silk panties. He led Jim to the tub and after testing the water temperature, he asked Jim to get in. Still keeping on his panties, Ralphie climbed in after him.
The water was hot, just like Jim liked. There must have been very expensive bath crystals in the water for it felt silky smooth and smelled heavenly. Jim noticed that Ralphie's panties were just about bursting from his huge hard-on.
"I get to wash and shave ya' but nuttin' else. Okay to kiss ya' but that's it. Keep my panties on. That's what Philip says. Keep your panties on. You like that word? Panties? Tha's what Philip calls 'em. Wants me to call 'em panties, too."
Jim admitted he did like the word, panties, and told Ralphie so. Then it hit him, 'shave'?
"Shave? I don't need a shave."
"Not your face, honey babe. Your body.all of you. Philip likes his ladies to be nice and smooth."
Ladies. Jim liked that thought too.
But first Ralphie washed his hair and head and chest and back and torso and thighs and legs and feet. He was very thorough but his touch was soft and gentle. The soft way Ralphie touched his feet and washed each individual toe was downright erotic. Jim told him how gentle he was. Ralphie smiled.
"Philip likes men who are gentle and ladylike. And I like touchin' you. Noticed I'm savin' the best for last?" he asked with a smile.
With that Ralphie reached down and began to slowly wash Jim's hard cock and ass. His touch was so soft and slow Jim hardly knew he was being washed. It was like a butterfly. Because of the silky smoothness of the soapy water Ralphie's finger slid into Jim's ass. He moaned slightly.
"Please don't cum, baby. Philip won't like it iffen ya' cum."
Jim tried hard not to think about what was happening. "Okay but you better stop now."
Ralphie stood and pulled Jim up with him. Holding Jim he kissed him lightly on the mouth. His tongue was full and soft on his lips. As his mouth opened, Jim moaned again.
"Hang on, baby doll. I still have to shave you."
There wasn't much body hair on Jim to start, but after Ralphie got through, there was none. He was careful shaving the hair off around his nipples and especially careful around his cock, balls and ass. It turned out to be a stimulating experience for both of them. Jim enjoyed the feeling of sitting on the edge of the tub and having someone carefully shave him.
By now they were both touching and kissing each other. Jim liked the feeling of moving his hand up and down Ralphie's panty encased cock. It was erotic. Jim noticed the expression on Ralphie's face as he kissed and stroked him.
"Oh shit. That's all for me." Ralphie said. "Let's get ya' dried off."
After getting out of the tub Ralphie took a large Turkish towel and dried Jim off. Then he took a bottle of baby oil and anointed him with it from top to bottom. Again he slowly massaged and caressed every inch of Jim's now smooth body. The feeling of the oil on his body was divine. He luxuriated in it. He turned and spread his arms and legs to allow Ralphie's hands to touch and oil every part of him. When he was done, Ralphie sprayed him with an old-fashioned perfume atomizer and then dusted him with a big fluffy powder puff and richly scented body talc. Lastly he sprayed Jim's hair and combed it for him.
"I feel like I'm being absolutely pampered. I feel like a bride!" Jim blurted out.
"Oh, you got that last part right, honey. You are ripe for the pluckin'" Saying that, Ralphie kneeled down and sticking his tongue far out gently licked the pre-cum off Jim's hard cock.
"Now you have to be prettified."
Ralphie sat Jim down at a large dressing table and began to work on him.
"First you need a nice lipstick. Bright red to match those sexy panties Philip has for you."
Jim sat looking at himself in the mirror as Ralphie transformed him into a woman. Lipstick, lip liner, lip gloss, eye shadow, mascara. Jim got it all. His fingers and toes were painted red.
While Ralphie fussed over him, Jim realized how much he really wanted and needed the change over. All his life he had been a man. Be aggressive. Take charge. But now he was yielding to his softer, more feminine nature and he was enjoying it. He wanted to be cared for. He loved the feeling of his smooth, sleek oiled skin. His hand touched himself again and again as he enjoyed the feeling of his balls. He looked forward to the red silk panties. The thought of them excited him. He wanted to be a woman.
"I think we're done. Like it?" Ralphie asked.
Looking at himself in the mirror, Jim waited a few seconds and then replied, "I love it! Thank you, darling."
Ralphie took a large dry clean towel and wrapped it around Jim. "Let's show you to Philip."
They walked into the bedroom where Philip was lying propped up on the bed.
"Oh, you look like a dream!" Philip exclaimed. "Thank you, Ralphie, you did a great job. I'll call you when we need you."
Philip stood and held Jim's hand. Then he slowly turned him around, as if admiring a new purchase. Sitting on the edge of the bed, Ralphie pulled the towel down so Jim stood there naked in front of him.
"Let me see you, darling. Turn around. Slowly. Show me all of you."
Jim did as he was told, slowly turning as he felt Philip's eyes devouring him.
"Come here, baby, and let's try these on," Philip said, handing Jim the red silk panties.
Jim held the bright red panties in his hand. They were light as a feather. Silk. Shimmering and sheer. Jim could see his hands through them.
"Oh my god. They're beautiful."
Still sitting on the edge of the bed, Philip took the panties from Jim and lowered them to the floor. "Step into them, darling. I want to see them on you."
Philip held the panties and Jim lifted first one leg then the other. He could feel Philip's breath on him as he slowly moved them up over Jim's oiled legs. Then they were on and Philip was smoothing and straightening them over Jim's cock and ass.
Leaning forward Philip kissed Jim's cock through the panties.
"Didn't take you long to get them wet," he said. "Do I do that to you?"
Then he pulled Jim onto the bed and began kissing him all over. Jim lay like a wanton woman, letting Philip's mouth trail warm kisses on his body. Philip's soft hands touched and fondled him. Jim's only reaction was to moan softly.
"Don't hold back, darling. Tell me what you like. If I excite you, let me know."
Jim's only reply was louder moans and sighs. He was on fire and Philip knew it. His mouth wetly wrapped around Jim's cock through the silky fabric. His mouth was soft and hot and Jim knew he was on the edge.
"Darling, please don't. I'm going to cum."
Philip didn't stop. His touch was so soft and light and erotic. His hands lightly touched Jim's nipples. It was all it took.
With a loud groan, Jim came. Philip continued to suck him through the cum soaked panties. The feeling was sensational. It was the first time and Jim absolutely loved it. The erotic thrill of the silky panties added to the sensation. He rocked slightly and came again and Philip continued to suck him off through the silky panties.
"You taste absolutely divine, darling," Philip said. "You have such a big clit and you cum so beautifully." He moved up and held Jim, wrapping his arms around him and letting Jim's head lay in the crook of his arm.
Jim was relaxed from cumming but excited, too. Clit? Yes, Philip certainly made him feel like he had a clit. He could still feel the panties and enjoyed the feeling on his ass as Philip caressed him. The silky feeling of Philip's gown excited him, too.
"When you're ready, let's try on the rest of these things, baby. I want to dress you up."
Jim readily admitted that he was eager to try on the rest of the silky apparel. Philip helped him on with a wonderful garter belt and then slowly slid a pair of red silk stockings up his legs fastening them at the top.
"Oh my. This feels so wonderful."
"I know, darling, I like them, too. I'm going to turn you into a lesbian and then you and I are going to make love to each other. Would you like that?"
It was like a dream come true for Jim. His lover, Philip, was turning him into a woman, something he always wanted, and then the two of them were going to make love to each other.
"Yes, darling, yes. I want you."
They were half sitting on the bed and Philip began to gently touch Jim's nipples. His nipples, the most sensitive part of him. He moaned.
Philip's reached to the nightstand and came back with some slippery lotion. He put a small drop on each nipple and then with one finger on each nipple he began to slowly flick the nipples up and down.
Jim looked down and watched Philip excite him. Up and down. Up and down. Slowly and softly.
"Like this, darling?" Philip whispered. Looking into Jim's eyes he leaned forward and their lips became one. Jim was so excited he couldn't think. He was only reacting. He sat there and was lost in a whirlpool of sexual feelings as he concentrated on Philip's lips engulfing him. The up and down motion on his nipples continued. He moaned continuously through the assault on his being. Lips and nipples merged as Philip lowered his head and began sucking on one and then the other.
His head tilted back, Jim gave himself to his lover. "Make love to me, darling, make love to me."
Jim's nipples were tied directly to his cock. The cock that just moments ago had lost all its cum was now hardening under Philip's lips and tongue and mouth being on his nipples.
"Oh, yes, baby, make love to me. Make love to my nipples. Make me cum again, please."
Philip was moaning now as he continued his slow sucking and licking of Jim's nipples.
"I need you now, baby," Philip said and raised himself up, calling out for Ralphie, who almost instantly appeared.
"Get the vibrator," Philip said.
Philip pulled down Jim's panties, and then pulled down his own, letting his hard cock spring into view.
In the meantime Ralphie returned with a plug-in wand vibrator that had a small strap attached to it. He fastened the vibrator to Jim's cock with the strap and tightened it.
Philip raised Jim's legs and Jim swung them over Philip's shoulders. Ralphie reached down and Jim could feel his ass being greased. Philip scooted forward as Ralphie guided his cock for Jim's ass.
Jim tensed and could feel Philip's hard cock nudging up against him.
"Oh god, do I need you!" he whispered. "Please, baby, fuck me!"
Philip was too experienced to just shove it in. Jim could feel the pain/pleasure as the first half-inch or so of Philip entered him.
"Yes! Oh yes, baby!"
Philip moved his cock a bit from side to side and slid in another half inch.
"Jees, yes. Give it to me," Jim pleaded. The sensation was incredible. He desperately needed Philip to fuck him up his ass.
Philip drew back slightly and Jim could sense the loss.
"No, oh no, baby, I need you!"
Philip pushed forward and gave Jim two more inches.
"Feel good, darling? Like this? Do you like being fucked?"
"Yes!"
Philip pushed and Jim half rose from the bed as he was filled completely with Philip's cock.
"Oh god, that's incredible. Ohhh, you're good!"
Again Philip began to withdraw and then pushed forward. Jim could feel his ass being fucked. Ralphie turned on the vibrator.
"OHH, MY GOD!" Jim cried out as the double sensation hit him. The vibrator hit his cock with all its intensity and Philip began to pump his ass in earnest. Jim thought he would cum immediately but having been drained just a short time before, it didn't happen. Instead he was having the absolutely best sexual pleasures of his life.
The vibrator was buried between Jim and Philip and had his cock in its own grip. It was beyond his reach and there was no way to control it, if Jim had really wanted to. But he let himself be used and pleasured. Soon he began shaking and mumbling incoherently as wave after wave of orgasm hit him without relief. Orgasms without cumming and he was wild. Philip was sparing no mercy but fucking him hard and fast. With a groan and a grunt he came and Jim felt his insides being filled with hot cum. Philip didn't stop a beat but continued hammering his ass.
When Philip was finally sated he slowed and then stopped his pumping action. But Jim was still on fire from the vibrator and continued moving and moaning. Philip withdrew and rolled to the side.
Ralphie took his place. His big hard cock slid instantly into Jim's ass and Jim looked up to see the smile on the young man's face.
"My turn, baby. And I'm going to fuck you to death."
He started slowly and with long deliberate motions, first filling Jim's ass and then withdrawing until Jim was afraid he would lose the marvelous feeling.
"Please," Jim begged, "Fuck me."
Ralphie had his own agenda. Slowly and steadily he continued to fuck Jim's ass as the vibrator hummed on. Jim was in spasms, shaking and moving his ass to match the vibrator's actions on his cock. Jim could feel his body being turned into a sexual tuning fork, strummed tightly by the vibrator and slowly caressed up his ass by Ralphie's big dick. He continued to babble and plead, moan and gasp from the onslaught.
As much as Ralphie wanted to continue, Jim's ass was just too hot and tight. He leaned forward and rammed home all of himself and let his hot cum mingle with Philip's. He was young and full of cum and was delighted to give it all to Jim.
Jim felt the cum up his ass as Ralphie made short movements to drain himself. Then the vibrator hit home and did its job and Jim came, too. Tensing himself he arched his back, lifting himself from the bed. His feet over Ralphie's shoulders, he shuddered and came. And passed out, absolutely drained of cum and emotion. It was too much; he simply passed out from exhaustion as visions of cocks danced in his head.