tagTranssexuals & CrossdressersBobbi from Tennessee

Bobbi from Tennessee

bycall_me_dana©

Six months ago ...

"I'm leaving now, Bob," Sue called out as she left. "I'll be back in a couple hours."

Bob waited until he heard the garage door close before going to their bedroom. He looked through Sue's underwear drawer before deciding on a sexy pair from Victoria Secrets. Walking down the hall, he opened the browser to a favorite porn site as he stripped off his clothes and slid the soft, feminine panties over his thighs. They were snug but he had learned to accept the tightness. Bob's hand lightly stroked his growing erection through the Sue's panties.

Sue waited forty-five minutes before sneaking back into the house. She had been finding small stains on her panties for the past few weeks and realized it must be her husband's cum on them. She figured he would either be in their bedroom or more likely, in the study where the computer was. Either place, she could see him without being seen herself. Sue was shocked but not surprised when she found Bob sitting in front of their PC wearing only a pair of her panties. His hand was inside the panties and she could see him stroking his cock. Sue watched him for a fifteen minutes without saying a word and Bob was oblivious to her being there.

Bob's hand was moving quickly up and down the length of his cock. As he felt his orgasm approaching, he pulled back the waistband of the panties to expose his cock. He closed his eyes and stroked up and down a few times before cum spilled from his cock and landed on his belly. When he opened his eyes, Sue was standing over him. Bob nearly fell off his chair when he saw her. "So THIS is why my panties have stains in them!" Sue's voice was loud but controlled as she pointed at the cum on his belly.

"Sue ... Sue," Bob stuttered as he searched for his composure. "What are you doing home? This isn't what it looks like ... I can explain!" Of course it was exactly what it looked like and he really couldn't explain but he could think of nothing else to say to his wife.

#

Two nights later, Bob arrived home from work to an empty house but a gift-wrapped package on the kitchen counter. Sue had barely spoken to him since she caught him in her panties. He opened the package and was shocked to find a pair of panties and matching padded bra with a note. The underwear was not quite as sexy as Sue's but when he looked at the labels, they were a size that would fit him - a bit larger than Sue's. The note read "If you want to wear women's underwear then put these on right now. Pour two glasses of wine, go to our bedroom, and call my cell to let me know you are wearing them and waiting for me. If you don't call me by six or you don't have them on when I return home, then I will expect you to never wear my panties again!"

Bob barely had to think about it before he had stripped off his clothes in the living room and stepped into the panties. They fit perfectly. He looked at the padded bra and thought about it before putting it around his chest. He had never tried one on but if this is what it took to wear Sue's panties then he would try. It took him a couple tries to get it on correctly but finally he had the bra and matching panties on and he was pouring wine. Bob walked to the bedroom and called Sue's cell. Sue had barely answered when Bob blurted out, "They fit! Please come home and see for yourself."

Sue smiled and turned to Bob's friend Roy, "I have to get home now. Thanks for the glass of wine (actually it was two)." Sue was only wearing a short skirt with low heels and a very revealing blouse with no bra. Sue and Bob have known Roy for about five years and count him as one of their best friends. Roy leaned against Sue as he hugged her good-bye. He could feel her hard nipples pressing against his chest as he kissed her on the cheek. Sue walked the three doors down to her house and entered.

Bob was lying on his side with his head propped by his hand. The two glasses of wine were on the night stand as he saw Sue stop in the doorway. She thought he was trying to look seductive but that's not what she had in mind for the evening. Suppressing a smile, "Stand up Bob and bring me a glass of wine." The lack of comprehension was obvious on his face and he didn't move off the bed. "I told you to bring me my wine so MOVE!" This got Bob's attention and he scrambled from the bed. He practically spilled the red wine as he brought it to her.

Bob started to say something but Sue silenced him. "Now turn around so I can see how they fit on you." Bob slowly turned in a circle about four feet in front of her. His erection was already evident in the panties. Sue took a long drink from the glass though she was already feeling the effects of the two glasses she had had with Roy. Bob made two complete circles before stopping and facing her. He wanted to smile but wasn't so sure that was his best idea. Sue took another drink before she put her hand on his bare belly. She could feel his body shiver at her touch.

First her hand moved up and cupped his cute little padded bras. "You have cute little titties, Bobbi." She had always called him Bob and this caught his attention. "That's right ... Bobbi. Bobbi with and 'i' when you are dressed like this for me." Bob grinned when he heard the last part. Sue's hand moved down his belly and Bobbi could feel his breathing grow shallow. Sue's hand moved over the panties as she felt his erection. He had already created a small wet spot at the tip of his cock. Sue took another drink from her glass as her hand caressed his cock through his panties.

Finally Bob realized that Sue's blouse was half unbuttoned and she wasn't wearing a bra. And he had had no idea where she had been when he called but it only took her a couple minutes to get home. With her hand still cupping his cock Sue said, "It's about time you noticed my blouse. Now I bet you are wondering where I was when you called but I'm not going to tell you." Sue could feel his cock leap in his panties. "Why don't you finish unbuttoning my blouse and show me what you think of my breasts." Sue has cute 34B's that fit her body well. Her nipples get very hard when aroused and they were already very hard.

Bob unbuttoned her blouse and lowered his mouth to her left breast. He sucked her into his mouth as his tongue flicked across her nipple. Sue gasped and squeezed his cock. Bob's tongue danced and teased her nipples as she continued to slide her hand over his cock and occasionally squeeze his balls. Sue knew he would lose control soon and finally she stopped him. Sue lay back with her legs hanging off the bed. Looking up at him she said, "Pull down your panties and cum on my tits Bobbi!"

It was like he had been shot with a gun when he heard those words. Bobbi quickly pulled down his panties and aimed his cock at her chest. He only had to stroke his cock twice before he came and came on Sue's cute tits. He felt so good about himself as his cum covered her boobs. Sue looked up at him, "Now pull your panties up and lick your cum off my tits and then make ME cum!"

Bob was dumbfounded. He had never tasted his own cum and he had never heard Sue talk to him like this. "Did those panties make you deaf? Lick my tits clean or I will throw those panties away tonight!" Bob quickly covered his cock and dropped to his knees. He leaned within a couple inches of her cum-covered tits and hesitated. Sue pressed his face into her chest and he felt his cum on his skin. Slowly at first, Bob licked his cum from her skin. After the initial embarrassment, Bob started licking his cum from her tits more quickly. When he was finished, he got between her knees and looked up at her.

Sue lifted her hips and pulled her short skirt upwards. Bob pulled her very skimpy thong over her legs and down to the floor. Sue's small patch of dark pubes were damp and matted. She reached over and grabbed the other glass of wine and took a big gulp. Bob lowered his face to her pussy lips and his tongue slid between them. He had always loved going down on her and knew this would be the best ever! His hands rubbed the skin of her inner thighs as his tongue lapped at her pussy. When he knew she was really feeling him, his tongue flicked across her clit. Sue was really turned-on by the power she was wielding and the red wine swirling through her mind and body. Bob had barely stroked her clit when Sue's body began to shake and her juices began to flow. Her thighs closed around Bob's head as his tongue flicked back and forth across her clit. His face was covered in her juices before she released his head from the grip of her thighs.

#

Over the next month, Sue and Bobbi had discussions about his attraction to wearing female panties and his new attachment to wearing bras. Sue bought him six more matching sets, one for each day of the week. They made the agreement that he could only wear them when she was home or when she gave him permission if she wasn't home. The first few days seemed awkward but by the end of the first week, Bobbi was showing Sue the websites he would surf while dressed when she wasn't home. Some were of women wearing skimpy undies or nude. And some were of men dressed like Bobbi was at the moment - panties and bra and a thin robe.

Some nights they would just sit and watch television or a movie with Bob dressed as Bobbi. He would almost always be erect but he wasn't allowed to get himself off on these nights - it was just two girls watching a movie. And some nights, Sue would tell Bobbi to go down on her and get her off. If she was feeling kind, she would let Bobbi masturbate. But if she wasn't feeling kind or didn't think he did a very good job on her, then he would have to go to bed in his bra and panties without any relief.

By the end of the second month, Sue had bought Bobbi a dark-haired wig for him to wear when he put on his panties and bra. Sue also bought Bobbi a couple outfits and had her wear them while they ate dinner.

#

On a Thursday morning in June, Sue got out of the shower while they both were getting ready for work and asked, "Do you know what today is, Bobbi?"

Bob, wearing his daytime briefs as he shaved, thought for a moment before shaking his head that he didn't know. "It's been three months since the night Bobbi came into our bedroom. I think it calls for a celebration."

"What do you have in mind?"

"Let's go to Rebounds tonight for dinner with you wearing one of Bobbi's outfits."

Bob nicked his chin and dropped the razor in the sink. As he tried to stop the flow of blood, "Are you crazy Sue? Clarksville, Tennessee is not that big a town! Someone will see us for sure ... see ME!"

Sue, still wet from her shower, walked up behind Bob and began to rub her smooth body against his backside. Her left hand slipped around and rubbed his chest while tweaking his nipples. Her right hand grasped his cock and began to stroke it. Bob could feel her breasts pressing against his back. He was still trying to stop the blood flow on his chin as Sue got him more and more aroused. "Oh Bob ... it will be so much fun! I promise. We'll get a booth in the back where we won't be too obvious to anyone." Her hand had his cock rock hard by now and Bob knew he was dying to go out dressed as Bobbi, he just hadn't told Sue.

When he couldn't take her attentions any longer, Bob turned around and pushed down his boxers. He took Sue in his arms and pressed his half-shaved face to hers. Their lips pressed together tightly and his tongue slipped into her mouth. Sue put her arms around Bob's shoulders and he lifted her onto the bathroom counter. Her bare ass sit on the cool tile. Bob reached down and pressed his erect cock against her pussy. Sue pulled herself forward and onto his cock. As she did, she wrapped her thighs around Bob's hips, pressing his cock deep inside her pussy.

This was the first time in the past three months that Sue had let Bob fuck her. She would let him jerk off occasionally and she had taken his panty-clad cock in her mouth a few times but she had always stopped him from fucking her ... until now. With Sue in his arms and his cock buried in her pussy, Bob thrust upwards with reckless abandon. His cock seemed to go deeper with every thrust. Sue was kissing his neck and nibbling his ear as it felt like he would split her open with each thrust.

Bob's lust quickly took over and well before he wanted to, his cock exploded deeply inside her pussy. He thrust a few more times but his orgasm took the steam from his body. Sue whispered into his ear, "Before I start to leak, put me on the countertop and get on your knees. Don't miss a drop!" Bob looked at her momentarily and then did what she said. His tongue licked deeply inside her pussy and he tasted his own gooey cum. A taste he had grown accustomed to over the past three months. Sue lifted her thighs over his shoulders and urged his tongue deeper inside her. He was so involved with eating his own cum from her pussy, he didn't even sense her orgasm until her juices washed over his face. As she came, Sue pulled Bob's head tighter to her pussy as she rode his face. Finally she released him and Bob fell backwards trying to catch his breath.

When his breathing returned to normal, he looked up at Sue and said, "Let's celebrate tonight." Sue smiled and tumbled to the floor on top of him. He could tell by her embrace the level of her excitement for tonight.

#

Bob could barely make it through the day. Every free moment, his mind would wander to the night out as Bobbi. Finally he could leave for work and he felt like he had to keep telling himself to not speed as he drove home. He stopped in his tracks as he walked through the door from the garage. Sue was lying on the couch and facing the door. Her blouse was unbuttoned and her left breast was exposed. She was wearing only her panties and she had them pulled to the side of her pussy. Her finger glistened as she rubbed her clit and slid them between her pussy lips. Smiling at him, "I just wanted to remind Bobbi what she will get to eat later tonight after our celebration!"

Bob shifted in the doorway, "WOW! Honestly, I couldn't keep myself from thinking about going out tonight all day long." Bob started to walk towards the couch but Sue removed her fingers and covered her pussy.

"Then you had better go get ready! I laid out something for you to wear tonight." Bob had the hurt look on his face but he merely kissed her lips on his way to the bedroom. Bob quickly showered and looking at his face, decided to shave once again. Sue joined him as he walked into the bedroom to get his clothes. He couldn't believe that Sue had bought him a thong for tonight. She wore them all the time but so far, his panties and been full-cheeked. "I thought we needed something special. Go ahead, slip it on."

Bob stepped into the thong and pulled the floss between his cheeks. His cock filled the small pouch. "I guess you'd better not get too aroused while we are out, had you?" It was a devilish grin on her face. With the wig in place, a padded bra, loose-fitting long-sleeved sweater, pair of jeans and flats and Bob had become Bobbi. Sue applied just a bit of make-up and she pronounced them ready to go.

Bobbi looked in the mirror and had some doubts but Sue pulled 'her' hand and they were headed towards the garage. Clarksville is a town of about 100,000 so once they left the neighborhood, Bobbi felt a little more at ease as Sue drove them to Rebounds Sports Grill on the highway. The parking lot only had a few cars - it was still pretty early and it was a weekday night. Bobbi eased out of the passenger side door and walked with Sue inside the place. Sue waved at the bartender as she led them to a spot near the back. They hadn't been there in some time so fortunately the waitress didn't recognize them.

With burgers and fries in front of them and the second glasses of beer, Bobbi was beginning to feel quite at ease for the first time. They had been talking about their day as if nothing was any different than usual. And then Roy walked by and waived at Sue. Roy - one of their best friends and the neighbor from down the street. Bob (and Bobbi) wanted to melt into the cushion at that moment. Roy walked right over to the table and said hello to Sue. "Roy - I want you to meet an old friend, Bobbi." Mortified, Bobbi looked up at Roy as he turned his look to her.

"Hello Bobbi. Nice to meet you." Bobbi couldn't believe that Roy didn't recognize him then and there. Bobbi merely smiled, afraid to speak a word.

Sue slid a little to her right in the booth, "Why don't you join us Roy?" Sue smiled across at Bobbi as she extended the offer.

"If I'm not interrupting anything, sure." Roy slid in next to Sue as he took a drink from his beer. It seemed to Bobbi that Roy sat awfully close to her. Then he saw Roy put his right hand under the table and Sue licked her lips as she picked up her beer glass. Bobbi quickly realized he had been set up. He wasn't sure what to do or say but just sat and watched as it became obvious Roy's hand was between his wife's thighs. Even when Bobbi spoke, Roy never let on that he knew it was his buddy Bob under the wig and sweater.

As they finished dinner, though Bobbi lost much of his appetite after Roy arrived, Roy suggested, "Why don't we stop back at my place? I have some beer in the fridge." Bobbi was shaking his head side-to-side at Sue.

"That would be great Roy! We're in my car so we can follow you." They paid on the way out the door and Bobbi hustled to the car.

"Are you crazy Sue? I can't keep being Bobbi - I'm sure he knows!"

She dismissed him with a wave as she backed the car from the slot, "You look great and we'll just have a couple beers and go home. You do remember what I showed you earlier, don't you?" Bob's mind flashed on her exposed pussy as he got home from work and as much as he tried to ignore it, his cock was rock-solid in his skimpy thong.

#

Sue pulled in the drive behind Roy's car. They climbed out of the car and went up the steps. Roy had left the door open for them and they walked right inside. Roy was already opening three bottles of beer. He handed one to Bobbi and motioned for her to take a seat on the couch. Sue then walked up to Roy and pressed her lips to his. He returned the kiss as Bobbi sat and watched, wide-eyed and jaw-dropped. Just as he started to object, Sue broke her kiss and gave Bob her serious look. "You just sit there and watch TV while Roy takes me to his bed. If we need something, we'll let you know." Bob was speechless and aroused at the same time. Sue had shared her fantasies of being fucked by other men but Bob never thought she would do it.

Just before Sue and Roy disappeared down the hall, she stopped and turned back to her husband sitting on the couch. "Oh, one more thing before we leave you alone for awhile." Bob looked at her with trepidation over what she might say. "Why don't you remove your sweater and jeans and show Roy your sexy underwear!" An ear-to-ear grin covered Roy's face.

"Please Sue. Don't ask me to do that ... in front of Roy!"

Sue frowned and walked over to Bob and whispered in his ear, "If you EVER want to fuck me again, you will do what I say NOW." Bob looked at her and knew she wasn't kidding with him. Bob, dressed as Bobbi and terribly aroused, stood up in front of the couch. Roy watched as Bob pulled the sweater over his head exposing his bra-covered 'titties'. Bob hesitated then pulled down the zipper of the jeans and pushed them over his hips and to the floor. His cock was pressing hard against the thong. He stood there as Roy looked him over before Sue walked away, taking Roy's hand as she did.

Bob was humiliated and so aroused. He took a long pull on the beer and his hand caressed his cock through the skimpy panties. It was no more than a few minutes before he heard the springs of the mattress and could only guess at what Roy and Sue were doing on Roy's bed.

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bycall_me_dana© 11 comments/ 65607 views/ 8 favorites

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