Marie: My Friend "Bobbie"

Author's note: These stories are inspired, one way or another, by the female half of bearlee. Either something she said or did prompted me to write it. There will be several with the categories changing from time to time and, although it may appear to be a series, each story is written to stand independent of the rest. Since her name has appeared in so many stories, as a change of pace, her middle name for the main character is being used. We hope you enjoy it!

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Bob had mixed feelings as he knocked on the door. Fear and trepidation on the one hand but excitement on the other. The door opened and Marie greeted him. She hadn't changed much since he had last seen her in high school. Still 5-7, long reddish-blonde hair and so slender and athletically built, she still looked the cheerleader he remembered from school. Even though he hadn't seen her since high school, they had kept in touch over the years. In a way, he now wished he hadn't shared so many of his deepest, darkest secrets with her, but felt relieved that at least someone knew and besides, he felt he could trust her.

Upon opening the door, she gave him a big hug and and welcomed him into her home. "Perfect timing, just enough time to get you ready before Tom gets home," she told him.

"So, what does he know?" Bob asked her.

"Just that an old friend from high school is coming over, that's it."

"Does he know, you know, about..."

"That you like to dress like a woman and have some fantasies you want to live out...no! Just the opposite really. He thinks you're an old girlfriend coming for a visit."

The bluntness of her statement took him aback at first. "Good," was the only response he could manage.

"C'mon, Bob, let's get real. It wouldn't work if he knew and I don't think he'd go for it if he did."

"Yeah, I know, I'm just not sure."

"You'll be perfect, Bobbie... that's what we'll call you, Bobbie!"

So, Marie was going to transform him into "Bobbie" and somehow he would get her husband to come on to him. He knew the role he would play. They had discussed it. Bobbie would be a slut, but still, it troubled him. He would be dressed as a woman for the first time with another man present and maybe, if he had the courage and everything worked out as planned, he might even suck a cock for the first time. But, even as difficult and confusing as it would be, compounding it would be the fact Marie was going to be right there watching him take a cock into his mouth for the very first time. There was more he thought about doing, but this was as far as he and Marie had discussed things for his initiation into this new world he was about to enter.

Marie took her friend's hand and lead him to her bedroom. Once there, she instructed Bobbie to strip. He liked the sound of his new name, but felt a little uncomfortable with her using nonetheless. Maybe it would have been easier if she was someone he didn't know all that well, but that was an impossibility he would have to deal with now. He had prepared for the evening by shaving all of his bodily hair off. Slipping out of his shirt, he slowly pulled his pants down. Standing in front of Marie in only the silky bikini underwear he wore, he could feel his cock begin to harden. He hesitated for a moment, knowing as soon as he pulled them down, his semi-rigid cock would come popping out in front of his old friend. Of course, the hardness of his cock was evident through the tight briefs, but still, he felt the embarrassment beginning to well up in him.

"Oooh, Bobbie, I see you prepared well for tonight, but that hard cock of yours, well, we've got to do something about that!" Her quick comment only added to the discomfort he felt, but she didn't stop there and it was her next comment that floored him. "Not sure how my husband would feel about that if he saw it!" A sense of dread coursed through his veins at the thought.

"Come on Bobbie," Marie said. "You don't have to be modest with me," she added, smiling. Her hand reached over and helped him pull down the small briefs. She handed him a pair of crotchless panties. He looked at her stunned at first, but slipped them on. Pulling them to one side to conceal his cock, it popped out anyway. Marie just laughed at his predicament.

"I guess that's not going to work, is it!" she said, laughing even more. Bob could feel his face turn a crimson color. "Bobbie, sit on the edge of the bed and jack-off; make yourself come!" Marie ordered him.

He did as he was told sitting on the edge of the bed, his hand moving to his cock. Slowly he jacked off, averting his eyes from Marie's watchful gaze and looking straight down at the floor. So many times he had jacked himself off, but never with anyone watching. He felt a sense of shame with her standing in front of him. Still, he knew many people would look at all of this as some kind of perversion, but she seemed so accepting of it.

"C'mon, Bobbie, look at me!" she teased him. His eyes moved slowly up meeting her's as he continued to massage his cock. The feel of the cool, crotchless panties and the humiliation he felt in front of his former classmate now actually made him more excited than he wanted to admit or wanted her to know. In a matter of minutes, his hot cum shot from his cock.

Marie moved her hand quickly as he squirted, cupping it over the head of his cock. When his orgasm subsided and the last of his cum was spilling from her hand, she wiped the thick, white residue on his lips and pushed her fingers into his mouth. "Taste it, Bobbie," she chided him. "Learn to love it!"

Things moved so quickly he wasn't completely sure what was happening. She helped him, pulling his shriveled cock down slightly forward and to the side along the front of his upper thigh fastening it securely with some kind of wrapping tape and gauze.

"There you go, Bobbie, if you don't get real hard, that should hide it for you!" Marie said, laughing again.

She continued to dress him putting on a lacy, foam filled bra, white frilly blouse and a ruffled skirt. Some make-up and a wig were added and when he looked at himself in the mirror, he smiled for a moment before turning back to Marie. In a feminine voice, he told her he thought he made a "passable Bobbie." She agreed and this time they shared a laugh together.

They heard the front door open. Marie put her fingers to her lips signaling him to be quiet. For his part, he stood frozen in fear. He knew the moment of truth was coming.

"Anybody home," they heard Tom call out.

"Be down in a second, honey!" Marie yelled back, her deep blue eyes lighting up at the prospects of the night ahead. "By the way, Bobbie, my friend is here," she added, calling down to her husband.

Marie gave him some final instructions. "Listen, we'll go down, say hello and he'll go up to take a shower. When we hear the shower running, we'll come back up. You wait in the bedroom and I'll hide in the closet. Then it's up to you."

Going downstairs together, Bob was thankful Marie had let him wear flats. At first she had insisted he wear pumps, but he had had enough trouble walking around the bedroom with them on let alone trying to make his way down the stairs.

"Honey, this is Bobbie, my friend from high school," Marie told her husband as they got to the bottom of the steps. Marie gave her husband a loving hug, then breaking away, Tom's hand extended to Bobbie to shake hands.

He wasn't sure why, but as their hands touched, he felt a spark of electricity race through his body and a slight tugging feeling against the tape on his leg. Tom was good looking and now, Bobbie, wanted the man standing in front of him.

"Listen, girls, I'm going up and take a quick shower," Tom said. "I'll be down in a bit. Nice to meet you, Bobbie."

With those words, Tom made his way up the steps. "Do you think he knew or suspected anything?" he asked Marie, his voice sounding both excited and anxious.

"Not at all...nope, not at all, Bobbie!"

They waited patiently until they heard the shower start. "Let's go, Bobbie!" he heard Marie say enthusiastically. Now, he was just as ready as she was even though he still didn't know exactly what was going to happen or how far he would go, if at all, when the time came.

Marie quickly moved to the closet, leaving the door slightly ajar. They talked quietly while the shower continued to run. So many questions raced through Bob's mind. Would anything happen at all? Would he suck the man's cock? Would he let Tom fuck him in the ass? No, that was probably out of the question. He believed he would give himself away for sure if that happened. It didn't matter anymore. The shower stopped and Marie signaled him to be quiet and wait.

Tom walked in the bedroom, a towel over his head drying his hair. Bob looked at the naked man. Tom was not immediately aware of the presence in the room. Bob stood quietly, trying to be confident, self-assured and exude a sexuality foreign to him. The towel moved from Tom's head and all of a sudden he saw Bobbie standing there.

"Shit, what the fuck..." he started to say.

"Shhh, it's okay!"

"Yeah, but Marie might..." he started to say in hushed tones.

"She had to run to the store to pick up something extra for dinner and asked me to let you know. I'm sorry, I didn't mean to startle you."

"No, it's okay, I guess. I mean, well, I would have put something on if I'd have known you were going to be in here."

"Marie said it was okay, that sometimes you guys do some swinging and it probably wouldn't bother you."

"Marie said that?" he asked, a devilish grin appearing and pushing his lips up at the ends.

"Yeah, she did." Bobbie smiled back at him and then quickly looked around the room. He saw a robe lying on the floor just behind him and turned to pick it up. "Here, you can put this on if you're embarrassed," he said to Tom, giving the man a peek at the back of his thighs and bottom of his panties as he bent forward, certain the cock taped to his leg was hidden and praying it was.

It must not have shown or, if it did, Tom didn't say a word as he took the robe and draped it over his shoulders. It hung down, open, exposing the cock hanging down between his legs.

"She say how long she'd be gone?" Tom asked.

"No, a while I guess. She was going to walk to the store."

He walked slowly over. "Well, Bobbie, maybe this'll give us a chance to get to know each other."

Tom put his hands on Bobbie's shoulders and kissed her deeply, his tongue probing her mouth. He pulled Bobbie tighter against his body. She could feel Tom's cock start to grow and push against the skirt and into her upper leg. Moving away, Tom's hand went to the padded bra and rubbed lightly. The first test was passed. Tom didn't notice anything unusual, but then moved his hand down to unbutton the blouse.

"No, don't! Marie could be back anytime."

Tom didn't argue the point. Instead, his hand went back to the padded chest and his other hand fell to Bobbie's pubic area and rubbed up and down. Still, Tom didn't know how close his fingers came to trapped cock, thanks to the preparatory work of Marie.

He kissed her deeply again and then, his hands on her shoulders, pushed her slowly down to her knees. Tom was stroking his cock in front of her face. Leaning forward, Bobbie kissed the head of erect cock before starting to lick the shaft. His tongue moved slowly down the shaft pausing to lick the heavy balls, then gliding back up the shaft letting his mouth drop over the head of the cock and taking it into his mouth.

Taking Tom's cock deeper inside the virginal mouth, Bobbie slowly started sucking. Her tongue circled over the head before she started moving her mouth up and down the shaft. She looked up, and seeing Tom's eyes were closed, knew for sure he really believed Bob was Bobbie, the little slut friend of his wife from high school, and loving the blowjob he was getting from her.

Bobbie's hand moved up and down the shaft of Tom's cock, following her lips caressing it, and with the other hand, reached around and grabbed at Tom's ass clutching it tightly. Bobbie wasn't sure what to do, but knew some of things Bob liked. She let one finger slip into Tom's ass, pushing it up and in as far as she could trying not cause Tom any discomfort and knew by the way his body responded he liked it.

At this point, whatever Bob couldn't do, Bobbie certainly could. She moved her head quickly up and down the shaft, then rested her lips just below the head, sucking hard. Her finger moved in and out of the puckered little hole of Tom's ass while his hips involuntarily pushed his cock in and out of her mouth. Bobbie's finger thrust deep, hard and twisting motion in his ass causing Tom's hips to shoot straight up and out forcing his cock deeper into Bobbie's open mouth.

Bobbie could feel Tom's asshole tighten around her finger and his body begin to shudder. Bob knew he was going to come and as Bobbie, he wanted to see it! Just at right moment, Bobbie moved her head back and held the head of Tom's cock in front of her face. Her mouth was open, waiting, as Tom shot his creamy load of cum into her mouth and over her face. As he finished coming, Bobbie took his cock back in her mouth and sucked it dry, hot cum dripping from the side of her face.

Tom stood for a moment over the young woman. He was still hard. "How 'bout we fuck!"

A feeling of panic shot through Bob. "Umm, I, well, I'm having my period," he said, his voice sounding nervous.

"How about in your ass!"

Now he was overtaken by another feeling of panic, more intense than the first. He stood up and turned around lifting his skirt and bending forward. Tom's fingers pulled the panties to the side and the sounds of a spitting on fingers could be heard just before two fingers pushed against the virgin asshole. Slowly, Tom pushed the head of his cock slipping just past the tight anal ring.

Bob's ass felt like it was on fire at first. The pain began to ease as the whole shaft pushed inside of him, burying itself deep into the tender, previously untapped ass. Different emotions were going through Bob's mind. He wanted this, he wanted to be fucked in the ass by the man, but he was afraid. It was all so new, but the real fear he felt was if Tom found out his identity and his mind wondered what the reaction would be and if Marie could intervene if it became necessary.

Tom started fucking his cock in and out her ass, pumping harder and plunging deeper. The pleasure overtook the fear and Bobbie tried hard to match the rhythm of the hard cock assaulting his ass. When Tom shoved in, Bobbie pushed back. One final thrust, Tom's hands gripping hard into the hips of his new fuck toy, and the feeling of hot cum flowing into the previously pristine asshole overwhelmed Bobbie. He could feel his cock fight against the tape holding it tightly against his leg. His cock tried to grow and expand but couldn't, remaining imprisoned by the gauze and tape holding it securely in place. He felt Tom withdraw with a popping sound and felt his cum leaking out behind it and trailing down his legs.

"I'm going to take another quick shower," he heard Tom's voice say before leaving the bedroom. Once again the shower water could be heard and Marie stepped out of the closet. She had a smile on her face, but moved past Bob leaving the room and making her way quickly downstairs.

Wiping off the cum from his face using Tom's robe he had left behind, he quickly followed her. On the way down Bobbie asked her if she thought he suspected. "No, not a thing!" came the reply. He felt a sense of relief when she spoke. Tom came down a short time later.

"That was a long shower, honey," she said to her husband. "I was hoping you'd get a chance to get to know Bobbie while I was gone."

All three of them exchanged quiet smiles. "Maybe later," Tom said. "What's for dinner?"

"Oh, I don't know, what would you like, Bobbie?"

"Something warm and creamy sounds good to me," Bobbie said, winking at Marie and then turning to wink at Tom.

"Maybe later," he heard the giddy Marie chuckle.

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