Bob continues his journey to a better Bobbie

This story is the next installment of the feminization of Bob, which began with him "dressing up" to go to a lingerie party with his wife. It is located at


In the months since that fateful night when Jean introduced her husband to cross-dressing and her girlfriends to Bobbie, much had happened. As you may remember, her mother was at their house when they came home from the party and was very interested in Bobbie.

Bob found a new passion. He loved the feminization Jean had done to him. He even enjoyed the cruel teasing the girls at the party had done to him. And he enjoyed the way his mother in law looked at him, standing there before her, as she put it, "Looking like June Cleaver gang banged." It was all worth it to get more of the slips and gowns he craved.

When Jean suggested to him that Bobbie needed her own room, he jumped on the idea. Jean told him that by remodeling the basement, they could put a bedroom down there for Bobbie. It would be a totally feminine room. There would be lots of lace and satin and pink and foo-foo. The closet would have to be big enough to handle a pretty good size wardrobe of dresses, gowns, slips and lingerie. No pants. Bobbie was not a pants girl.

Now it was a reality. As Jean and Bob/Bobbie stood in the doorway, admiring their work, Jeans hand went instinctively to Bob's crotch. He was hard as a rock. The closet was a double bi-fold door type and was half full of gowns and robes, a quarter full of slips on hangers and the last quarter, dresses.

"You like Bobbie's new room, sweetie?"

"I love it. I can't wait till she gets to try it out," he said. "You want to try it out first?" He ran his arm around her waist and up to her breast. She wasn't wearing a bra. He noticed her nipple was hard. She leaned into him and began to stroke him.

But lets go back to before the room became a reality. Let's see the journey Bob took.

Joan called Jean the day after the party, about mid-morning.

"Good Morning, Dear, and how are the girls and your man today?"

"Mom, Bob is still asleep. Poor dear really got a going over last night and is still recuperating. I got a very good night's sleep and am up to my armpits in laundry. What's up?"

"I am dying to come over and get to see Bob put on his show. "

"No dice today, Mom. Let him have his rest. Tell you what. Come over tomorrow about ten and he'll be ready."

"It's a date dear. See you and Bob tomorrow."

Jean really didn't want to give into her mother, but she could be very insistent, especially when it came to erotic humiliation of men.

"Oh, what the hell," she thought. "He is getting into more than I thought and is enjoying it a lot."

The next day was rainy and cold. Perfect for this little party. There would be few if any, distractions.

Joan showed up a few minutes early and Jean could tell by her attire, she had plans for Bob. She wore her black leather skirt with black silk blouse, neckline just low enough to hint of cleaveage. Jean knew that meant a black slip, bra and panties (if any) beneath. She had to admit, though her mother was in her forties, she cut a striking figure.

Jean brought out her mother's slip, neatly folded, and placed it on the coffee table. The two women sat down on the sofa with their coffee and made small talk.

Jean had gotten Bob up earlier, letting him sleep as long as possible to recuperate. She could hear the shower running and knew he would join them shortly. She had not told him his day was already planned.

Bob entered the living room in a bathrobe, still drying his hair with a towel. He was on his way to the kitchen for a cup of coffee.

"I have your coffee here, sweetie," Jean said to him.

Seeing Joan there surprised him. He took in the view before him as eye candy before greeting her. He had always been physically attracted to her. Today, she was something special. The combination of her raven black hair, blue eyes, china colored skin and that very full black silk blouse ("those breasts have got to be 38C or D") caused a stir within him, even before his eyes got to the long shapely legs in that leather skirt.

"Hi Joan, what brings you to our place today?" he asked as he sat down opposite them.

"Actually, you do, Bob," she answered, looking him square in the eye with a slight smile.

Bob had not remembered the discussion the night they returned from the lingerie party. There were too many other events of that night fresh on his mind.

"You see," she started, "I noticed that I was missing one of my good slips a while ago. After thinking about it, I remembered that it was in the wash the day I came over to use your machine when mine was broken."

Bob had a feeling of dread rising up. He remembered all too clearly. He had seen the slip in the basket as she went to the laundry room. He debated for a while but finally he had stolen the slip from the basket as it sat in the laundry room. He could sense what was coming next.

"So I called Jean to ask if she had seen it. She told me she knew right where it was, and some other interesting things," Joan said with a wry smile and a raised eyebrow.

Bob remains silent. He is feeling increasingly uncomfortable.

Jean chimes in. "You know where I found that slip, don't you, sweetie?"

"Yes," he says sheepishly

"I want to hear your explanation," Joan said. The gleam in her eye told her daughter she was enjoying this.

Bob had his head down, not knowing what to do next. He picked up the coffee mug Jean had set out for him. He took a big gulp. To his surprise, Jean had laced it with a healthy shot of Irish whiskey. He took another gulp. He knew he would need it.

"Bob, tell me why you took my slip."

No answer.

"Do you like women's clothes? Do you like to wear them?"

Bob was clearly embarrassed and Joan was enjoying his predicament. But she saw something else. Something told her that he also was finding this exciting. And he was.

"Bob, answer Mom. I want to know too. I want to hear it from you."

"Why my slip, Bob, and not my bra, or girdle? I bet you like the feel of the slip, don't you?"

"Yes," his head still down, his face flush from embarrassment.

"You like the feel, don't you? The feel of the silky nylon against your skin."

Bob nodded almost in-perceptively. He still could not bring his head up to look at these women. He took another gulp of coffee. It was starting to help.

Joan got up and came around the coffee table and stood next to him. Her hand rubbed his hair.

"Do you think you are the first man to like slips? Who do you think designs these beautiful pieces of clothing? Men design them supposedly for women but I think its as much for themselves."

She picked up the slip from the coffee table and held it by the straps. It cascaded down as it unfolded until it hung full length just inches from Bob's face.

"Isn't it pretty, Bob? You like that part too, don't you? But most of all you like the feel."

She drug the slip across his cheek. He didn't pull away and she heard him gasp.

"Now that we have that established, I want you to tell me what you did with my slip."

There was no way out for him and he knew it. And part of him wanted to look her in the eye and tell her that he had taken that slip and gone into the guest room and got naked with it. Then spent the next half hour playing with its silkiness until he could postpone the orgasm no longer. He came, and came, and came. As he thought through that, a strange sensation came over him and he looked up at her.

"I took it to bed and masturbated with it," he said, evenly and looking directly at her.

"Now we are getting somewhere," she replied. "Go On."

She walked around behind him and drug the slip around his neck.

"What else is there? I just told you what you wanted."

She walked back around to his front and knelt down. She looked him dead in the eye as her hands grabbed the robe on each side. She waited just long enough to see the recognition of what she was about to do in his eyes. Then she yanked the robe open. In a flash he was totally exposed. He was hardening fast and the robe, until an instant ago had hidden the evidence.

Even Jean jumped at the suddenness of the move her mother had just made. But she had to admit; her mother was very good at this.

"Well, it seems that just the discussion of a silky slip can get you going."

The booze in the coffee had done what Jean had wanted. It had de-inhibited Bob. Now the second special ingredient would come into play.

Bob looked up at Joan with pleading eyes. But it was no use. The look he got back told him there would be no mercy now. There was a slight smirk on her face as she looked into his eyes.

"Now we know how you like silky slips, we need to find out you satisfy this hunger, once aroused."

Bob did not realize he was turning on faster than usual. All he knew was the embarrassment and the wanting of that slip were all mixed up.

Joan, still holding the slip by the straps, drug it to his face, the skirt of the slip grazed the rapidly hardening cock and she heard him gasp. She repeated the maneuver, as much for her pleasure as his.

Desire finally overcame Bob and he put his hand out to press the slip against his cheek and cuddle it. His erect cock twitched at the feather touch of the skirt of the slip.

"What do you want from me, Joan? What do you want me to do?"

His other hand found the slip and brought it to his body, at his belly first then working down until he molded the silky slip around his cock.

"Nothing you don't already want to do sweetie. Nothing you have not already done with my slip. I want you to enjoy my slip the same way you did the first time. Only this time you are going to have an audience. Your wife and I are going to watch you as you make love to my slip."

She turned to Jean.

"Shall we adjourn to the bedroom?"

"The guest room bed is made."

"Bob, stand up and come with us. And now that your secret is out, just leave your bathrobe here."

Joan had originally wanted to take Bob in his own bed. She knew doing that would be additional humiliation but in deference to her daughter she didn't push it. She started down the hall with the slip over her shoulder as if leading a horse with a carrot. Bob followed dutifully, naked and erect. Jean brought up the rear, a smile of amusement on her lips.

Once in the bedroom, Joan quickly pulled down the covers and motioned for Bob to make himself comfortable. He obeyed and laid down on the bed, looking up at her with a mix of fear and desire. His cock stood straight up. She teased him by dragging the slip across his manhood till it twitched and he reached for the silky tool of torment. Then she pulled it away.

"Not Yet," she said.

Bob was now feeling the full effects of that second ingredient in his coffee. He was on fire with desire. All he could think of was cumming. He wanted to give them the show, NOW! His sacks were even beginning to hurt.

"I know you may be a little self-conscious, laying there naked while we are fully dressed, so I guess in order for you to be more relaxed...", she paused as she started unbuttoning the exquisite silk blouse she was wearing; "I will give you some eye candy."

She finished unbuttoning the blouse and then reached around behind her to undo her skirt. He heard the zipper and her hands came around to her sides as she pushed the skirt down.

In the dim light of the bedroom, he did not immediately see where the skirt ended and the blouse ended since there was only black behind them. As he heard the skirt hit the floor, he saw her open the unbuttoned blouse. The sight of the black lace trimmed slip and her china white skin struck him. He laid there with his mouth open in awe. It was a beautiful site. The slip was obviously a very good one. The ribbon straps were slightly wider than normal. The lace was breathtakingly elegant in the way it trimmed the top of the slip and wrapped around the shinny nylon covering her breasts. The lace on the hem was a good 3 inches with a nice side split also trimmed in lace. The main fabric of the slip had a sheen that only fine quality nylon has. If he had been capable of that kind of thought at this moment he would have known that this slip must have cost over $100.

"Well, do you like what you see, Bob? "

"You look good enough to eat," he said, breathing heavily.

"I may make you prove that later," she taunted.

In back of Joan, Bob saw Jean step out of her skirt and take off her blouse. She was wearing a royal blue half-slip and bra. She undid the bra and let it slide to the floor.

Finally, Joan again picked up the slip by the straps, laid it on Bob and let it drop. He reached for it and pulled it up and buried his face in the white silkiness. He was beyond caring what they saw. He wanted that slip to take him.

"Lay the slip out on your body so you can feel the maximum amount of it. I would love to see you in it but then couldn't see you cum. And I want to see that. I want to see how you cum for my slip. You may begin but slowly. Don't rush."

He knew that even going as slow as his passion would let him, it would not put off the inevitable for long. And when he gave them the final act, the climax, it would be in copious amounts. Surely his body would pump out gallons for this. He hadn't yet guessed how that would be played out, but Jean had plans she hadn't even told her mother.

His hands roamed the slip. They went down his thighs, up his torso and played with his nipples through the nylon cups. Then his hands began their journey to the bulge in the lap of the slip. He closed his eyes and savored the pleasure as his hand wrapped the nylon around the cylinder it encased. Almost as soon as he did that a small wet spot appeared.

The girls, seeing this joined him on the bed; one sitting on either side of him. Jean positioned herself at the head of the bed so her hips were pressing her slip against the side of his face. She looked at him and smiled.

Joan took his free hand and guided it to the black beauty she was wearing and guided it up her inner thigh. He squeezed her thigh but never lost concentration on his assigned task. He wrapped nylon around his sacks and continued to stroke as slowly as he could. He was enjoying every fiber of this slip and all three knew it. She pulled the slip in his lap aside to inspect his member. There was a small drop of pre-cum just emerging and she reached for it with one hand. The other went to the base of his cock and milked the full length.

The small drop increased to almost a teaspoonful and she collected it on three fingers. Then she brought it part way to her lips. She brought out her tongue, making sure he was watching, and licked some of it up.

As if changing her mind, she stopped and said "No, you take this." Then she brought the three fingers to his lips. She smiled while he hungrily licked her fingers clean.

"Good Boy," she mocked, then leaned over and kissed him. As she did, her hand went down and joined his. She interlaced fingers with him and took over the rhythm to match the rhythm of her tongue working in and out of his mouth. She felt him start to tense and knew she had to break it or miss the orgasm she wanted to see. She pulled back and let go.

Jean had seen this and intervened. "Let him cool off for a minute, Mom. The ending will be worth the wait, I promise."

Then Jean repositioned herself across the head of the bed with Bob's head in her lap. He could feel her blue silky slip against his neck. She let him nuzzle her slip-covered lap for a few moments then kissed his forehead and guided his hand back to his cock. This time, her hand went under the slip and expertly milked him with one hand. She brought out three fingers covered with pre-cum and brought it to his lips. He purred as she fed it to him. His hand started to move the slip up and down again and quickly he regained what little passion had been lost in the brief interlude.

Joan was sitting facing him and stroked his inner thigh with the slip. She smiled as she saw him lost in the pleasure of her slip. This was more than she had hoped for.

Jean knew the signs of his impending orgasm as he got closer. At the first indication she started moving him to a more upright position. She told him it was so Joan could better see his orgasm. As she got him in a sitting position without him loosing any passion, she knew her special victory was at hand. He was breathing very hard and in short gasps.

She leaned over and whispered in his ear, "Show mom what you did the other night at the party, honey. Let her see what you did."

"No, Jean. Don't make me do that. Please."

"Sweetie, please do it. She would love to see that and you know you really enjoyed giving that show. "

As she was talking to him, her hand had come up to the nape of his neck. He felt her start to press down.

"Come on, sweetie. Show her. Let her see you cum like you did that night."

He could feel her hand pushing his head down. He could not resist. Then his face was just inches from the bulging nylon. Jean reached down and uncovered the head of his cock and squeezed his hand.

"Do it, baby. Let us see you shoot your cum all over your own face."

Joan had not quite realized what was going on until she saw the first rope of sperm fire from his cock and hit him across his nose. Then the second hit him in the right eye and up over the eyebrow. The third hit his mouth and covered it. The fourth hit the left side of his face. The last of the cum just came out and oozed down the helmet of his cock and collected in the nylon in his hand at the base.

Joan was speechless. The look of wonder on her face spoke volumes.

Finally she spoke. "I have never seen that before."

"Mom, this pervert just showed you what that slut Wifey is doing on his computer screen while he is using your slip."

Jean had hold of Bob's head and was cleaning his face by squeegeeing his cum into his mouth. He was too exhausted to fight it. He swallowed it all.

"After that, daughter, I am so hot, I must make him prove what he said earlier. Finish cleaning him up."

Jean picked up the slip from his lap and before she wiped his face, she made him lick the collected cum that had oozed out from it. After she had wiped his face, she got up off the bed.

"He's all yours, mom. Have a ball."

Joan looked at him as she stood up and took off her underpants and unhooked her bra, studying him.

As she climbed up on the bed and straddled him, she lifted the slip and straddled his face. He eagerly kissed and tongued the womanhood being fed to him.

"Actually, I was thinking I would rather have a tongue than a ball."

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17701 days ago, 2391 reads
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