Greg had been wearing his new gold chain for about a month and during that time things had again changed in his relationship with Jill. She had decided that he should become more of a sissy boy. He had evolved to the point where he enjoyed and looked forward to Jill’s sexual experiences with other men. He enjoyed licking and drinking their semen and had become good friends with Colby, always welcoming him into their home.

To further Greg’s change in lifestyle Jill had gone to the mall on a Saturday morning where she bought him a selection of panties, camisoles and a nightie from Victoria’s, several miniskirts and various feminine pull over tops at other stores. She also picked up a gold ankle bracelet that she had had made. It had two charms on it, one an ace of spades symbol and the other a small key symbol. She placed it on her left ankle and was very pleased with the look.

After she arrived back home, she told Greg that they needed to talk. She discussed the changes in both of them and in their relationship. He agreed with all she had to say. He had changed. Their relationship was different. He was more submissive and enjoyed a heretofore unspoken feminine role. At that point she presented him with the panties, camisoles, miniskirts, tops and the nightie. She had already cut a slit in the front of the panties so his cock and cage could hang through.

“From now on you will wear women’s panties and camisoles all the time and when you are home you will wear the miniskirts and one of these tops. You will sleep in the nightie. When you get fully used to them, we will go shopping together to find other female clothes for you to wear at home and under your work clothes. Now go take a shower. Your pubic area needs shaving and from now on you will also shave your legs and keep them totally smooth.”

He was a bit startled by what she had told him but deep inside he knew this was just another step down the road they were following. He made no comment as he went to shower as instructed.

When he came out of the bathroom, she was waiting for him in their bedroom. “You look wonderful honey! Your smooth legs are beautiful. I’ll bet they feel good to you.”

“They do feel good. I have to admit that I have thought about doing this but it took you pushing me to make it happen. Can I pick out a pair of panties and a cami?”

“That is a wonderful idea,” she said. Happy that he had so readily begun his transformation.

“I think I like the pink panties and white cami,” he said.

She handed them to him and he slipped them on. “Oh I love the soft smooth feel of these. They are very comfortable. Thank you for picking them out for me.”

“You are quite welcome,” she said as she handed him one of the skirts and a top. “Put these on and we will see how you look.”

He pulled up and zipped the skirt and pulled the top over his head. She told him how fabulous he looked. Looking in the mirror at the new Greg, he was amazed at his transformation. “My legs really do look quite good don’t they?”

“Yes Dear, I think this suits you perfectly. I love the way your cock is just barely hidden. Colby is also going to love the new you. Come here and give me a big kiss!”

During the next week she prepared him for his next step, anal sex. She explained how wonderful it was, after all he had seen her take a cock in her ass many times and have numerous orgasms from it. He was a bit reluctant at first but again he knew it was the role he had willingly chosen.

After he accepted the idea, she had him get on his hands and knees on the bed and, after lifting his skirt and pulling down his panties, gently inserted an anal plug. She explained they would start with a short time and then extend it until he was fully used to it before she would actually use the strap-on silicone cock she had purchased to fuck him.

Greg readily took to his new situation. He loved the soft colored panties and camis. Wearing the skirt and blouse at home also pleased him. He was surprised at how quickly he was becoming accustomed to the clothes and anal plug. He began to look forward to his first fucking by Jill.

While all this was evolving, Jill spent time having sex at Colby’s house, not yet wanting to bring him to the house until she was sure of Greg’s acceptance and complete transformation. She reveled in Colby’s attention to her; the countless screaming orgasms he gave her and the cum with which he filled her. Life was good.

He had immediately noticed the new anklet she was wearing when she arrived on Monday night and recognized its significance. He told her it looked really good on her and that it was a good way to subtly show people, who recognized it’s meaning, what her status was; it could result in more fun for both of them. Greg had also noticed it but was clueless about its meaning. He did tell her he thought it complemented her beautiful legs very well.

She did tell Colby everything that was going on between her and Greg so that he would understand the new situation when she invited him back to the house. She also asked him to consider letting Greg have some sexual contact with him. He told her that he was reluctant about that but he would consider it. They had discussed her goals with Greg so he understood it was not a gay thing but that it would be a recognition and affirmation by Greg of his new role.

On a Thursday night, which would have been the sixth night of having the anal plug, Greg told Jill that he was ready for her to fuck him. He had shaved everything he was supposed to and really needed sexual release. He had not had any climax in over two weeks. Meanwhile he had been licking Jill clean almost every night after she arrived home from Colby’s. Jill was happy he had asked for it. It meant he was almost fully adapted. It would be almost complete after tonight.

They had talked about how it would work and Greg had read about male sexual response from anal fucking. He fully expected to have an orgasm and ejaculate a large load which he would catch in a glass he would hold. But first he had to orally bring Jill to orgasm, which they both loved. He was more than ready.

They went into the bedroom and after their preliminary amorous fondling and kissing Greg went to work on her pussy. She was spread wide for him and he took full advantage. He knew her every spot and soon she was writhing and moaning.

“Eat me Baby! Suck that clit! Oh yes, just like that! Keep it up, keep it up. Oh god I am so close, do it do it! YES! Oh fuck that is perfect!”

She finally had to push his head away, her clit was too sensitive. She lay there panting, her heart slowing back to normal. After they kissed and cuddled, she freed him from his lock and arose to put on the dildo, telling Greg to get up on his knees, head down. She handed him the glass they both knew he would need.

After getting behind him, she lubed the dildo and his hole. He was already semi hard in anticipation. Both of their hearts were pounding. They were both entering territory neither had ever been in.

She had practiced for this moment by wearing the harness and dildo and making the motions while loosely holding the dildo. Greg was ready from his days with the plug in him. She rubbed the pole up and down his ass, gently probing his opening. He audibly sucked in his breath with her first venture in and out of him. The next thrust was only in. Slowly in and a bit out, deeper each time, she increased her speed as Greg starting to moan more and more.

It came naturally to her. She developed a rhythm based on his response. Deeper and deeper until she had fully penetrated him. He was moaning in pleasure. His cock was hard, pointing to the bed. She reminded him of the glass and he held it around his cock; his face buried in the bedding.

“Oh my god! I can’t believe the feeling. Fuck me, do not hold back. I need to cum and you are driving me toward it.”

He continued his moaning mixed with what she hoped were tears of happiness. He begged for release. She rubbed his balls as she fucked him harder and faster.

“Oh yes, my god I am cumming!”

She glanced at his cock and saw it pulsing stream after stream of a thick white spore into the glass. He began to collapse. She withdrew the dildo and he fell face down to the bed. She snagged the glass before it fell over and then lay beside him, the dildo pointing straight up.

Slowly she arose, putting the glass on the end table and removing the harness. He gradually turned over and she leaned down to kiss him.

“Honey you were wonderful! I loved making you cum like that. Maybe now you have a better understanding of my feelings for it.”

“I never thought I would say this but I loved you fucking my ass. I am a different person and I am totally happy. The smooth legs, the new intimate things, everything you have done. I am your sissy boy and I love you.”

“I love my little sissy boy also. Go take a shower, I have another present for you.”

He looked at her with a questioning look but knew enough not to say anything. He disappeared into the bathroom. She retrieved her present for him.

He soon reappeared, clean and dry, his penis shrunk back to its normal small state. “What do you have for me?”

“I bought a new lock for you. It is an all stainless steel cage that should give you better air circulation; a more open feeling but still locked tight. Here, put it on and tell me how you like it.”

He took it and examined it carefully. “I do like its design,” he said as he fitted it around his balls and cock. He snapped it together and walked around a bit.

“It is comfortable. I like it better than the plastic one. Thank you for thinking of me.”

“Well it looks very good on you. More ‘manly’ while still keeping you tightly locked. I like my new sissy boy. I am very happy that you have adapted so well. This weekend we will have Colby over to see the new you. I have told him all about the changes that have been taking place. He is looking forward to seeing you again.”

“I have missed him and the three of us being together.”

Picking up the glass he had spurted into, asking him if he wanted to just drink it down or have her prepare a cocktail. He opted for the cocktail. She went to the kitchen and blended his seed with their favorite, Grey Goose. She joined him with some plain Goose on the rocks.

They both enjoyed their drinks and soon fell asleep for the night.
 
The next day was Friday. The weekend was almost here. They both went through their morning getting-ready-for-work rituals. This would be Greg’s first day in his new feminine panties and cami, he loved their feel as he slipped them on.

During the day Greg received two comments about his gold chain and lock, one from one of his grad students and one from a female professor in his department. The student had told him that he liked his gold chain, remarking that it was very unusual and he was cool for wearing something so different. His female colleague had reached to examine the lock, rubbing it between her fingers, and telling him, with an amusing smile, that she approved of his new lock and chain.

“So Greg, any special significance to this?” she asked.

He blushed a bit and said, “No Cathy, it was just a thoughtful gift from my wife.”

“I might like to get one for my husband. Where did she get it?”

“I really don’t know,” he said. “You would have to ask her.”

“Find out for me and let me know Monday, thanks.” She handed him her card and abruptly turned and walked away.

He was a bit taken aback by her demeanor since she was junior to him in the faculty. After thinking about it a bit he wondered if it was possible her husband was also a cuckold. He would ask Jill for the chain information and see how she reacted. It was getting late so he headed home. When he arrived, he saw Colby’s car was there. He was inside with Jill.

He felt a mixture of happiness and anger. He was happy that Jill was happy, that she had found a satisfaction he could not give her and she still wanted him. He hated to admit it but he liked Colby. He was a nice guy and treated Greg as a friend not like some useless, unwanted husband. He was mostly angry with himself, that his failings had put him in this new position. But he was actually enjoying it now and for some reason that he could not fathom, that also made him angry.

He went in the house where they were already having wine and cheese. Jill was wearing a cropped tee shirt and a denim mini skirt. Colby had on jeans and a tee shirt. Besides his sexual status with Jill, he was more athletic and muscular than Greg and it showed.

“Sorry I am late, work held me up as usual.”

“No problem Dear, Colby and I have been enjoying each other,” she said with a big smile.

Once again the same thoughts raced through his mind. He headed for the bedroom to change clothes. Jill grabbed her wine and followed him. She wanted to make sure Greg did not hesitate to put on his mini skirt and new top. There was no reluctance. He took off his work suit and put on his skirt and top without an apparent thought.

He did take time to explain the request regarding his chain from Cathy. Jill thought about it and was intrigued so she told him to give her Cathy’s card. He was a bit reluctant but gave her the card. She told him she would call this weekend and talk directly to her. She kissed him on the cheek and left, telling him not to mention this to Colby and to come and enjoy the appetizers when he was ready.

When he came out, Jill was snuggled up to Colby on the couch, eyes closed, sipping her wine and gently, slowly brushing his cock through his jeans. He had his arm around her and was playing with her left nipple, which was hard as a rock. She was quietly moaning.

Colby smiled at Greg. Jill, finally realizing that he was there, asked Colby what he thought of Greg’s new look. He told Greg that Jill had kept him informed about the changes that had been taking place and that he thought it was wonderful that they had worked out a relationship that made them both happy.

He asked Greg to come over and show him his new lock. Greg came right over and lifted his skirt so Colby could see it.

“That looks more comfortable than your other one. Do you like it?”

“It is more comfortable and I like the cool feel of the steel instead of the hot plastic.”

“Well that is great. Sit down and enjoy the wine and cheese with us. I understand you are going to grill your great steaks for us later. I am looking forward to that.”

Greg sat in a chair across from them. Colby and he discussed work and the news as Jill totally ignored them both, lost in the stimulation she was receiving from Colby.

After a very good dinner, Jill told Greg to clean up everything and then join her and Colby in the bedroom when he was finished. He acquiesced as they left.

When he finished and came into the bedroom he found them both nude with Jill sucking Colby’s large cock. He had previously told Jill that he really wanted to try sucking Colby’s cock. Her obvious intense pleasure had made him very curious about how it felt. She had promised to talk to him about it but nothing more was said.

Jill heard him come in and looked up at Colby. He gave her a slight nod. As Greg was on his way to sit in his corner chair, she told him to come over to the bed.

“Take off your clothes and you can suck Colby for a bit. Be gentle, no teeth! Stop when he says so. I hope you enjoy it.”

Greg quickly stripped, thanking them both in the process. He got on the bed and took her place between his legs. He carefully took Colby’s cock in his mouth and using just his lips and tongue, began to lick, suck, caress and fondle his beautiful huge black cock. It felt wonderful to him. He began to understand Jill’s pleasure. There was so much he did not know and was beginning to learn.

Colby knew this was not a gay thing but the curiosity of a straight man that wanted to learn and understand his wife and her sexual pleasure. He let him go on for quite a while. Greg was really quite good at it. But he really wanted Jill so eventually he stopped him and she returned to her place between his legs.

“Thank you so much! I am beginning to understand Jill’s enjoyment. I have one favor I would like to ask that would really complete the night for me. Please, please consider when you and Jill are fucking and you are ready to cum, call me over and cum in my mouth so I can experience that also. I know it is very much to ask but please just consider it.”

Colby told him he did understand and that he would give it serious thought as the night progressed. He then reached down to Jill and pulled her up on top, impaling her with his cock. Greg went to his seat.

Colby and Jill locked hands for her support as she began to move her hips, rubbing her clit back and forth on him while keeping his cock fully buried in her. They both knew that this was one position that brought her many orgasms and it would start soon.

“Ohh yes, I am soo stuffed with cock! Fuck, oh fuck, oh fuck, damn, yes NOW!”

Her body began to shake as her screams rang through the room but her hips never stopped their urgent back and forth motion. Orgasm after orgasm rippled through her. Her juice could be seen running over his abdomen and onto the towel covered bed. Head thrown back, eyes shut tight, she seemed almost possessed. Sweat was beading on her body, running down her back and chest, trickling between her breasts. Colby could feel her legs trembling as they were pressed against him. Finally, gasping for breath, she brought on one last extended, strong, orgasm causing her to lose control of her arms and scream out a series of unintelligible words as she fell to his chest.

She laid still, trying to recover her senses; half the length of his cock was still in her. Slowly her chest stopping heaving so heavily and she rolled off onto her back. Colby told Greg to bring her some water, which he quickly did. She propped herself up on one elbow and thirstily consumed all the water in one long drink.

“Every time I do this with you it ends this way. I lose control of my hips and drive myself into a state of almost perpetual orgasms until I collapse,” she said. “I would not trade this enormous thrill for anything!”

“Greg, bring your chair over next to the bed,” said Colby. “I am going to give you your wish. She is going to lie on her back and I am going to fuck her until I am ready to cum and then I am going to finish in your mouth. Be ready and you had better swallow it all!”

“Oh my god, thank you! I will be right here so when you pull out I can immediately take it. Thank you so much!”

Colby pushed Jill’s exhausted legs apart and entered her to his full depth causing her to gasp and come fully awake. Greg sat near where Colby would be when he finished.

“I don’t know how much more I can endure,” Jill whispered.

“You are going to take as much as I feel like giving you,” he said as he lifted her legs and put them under his arms. “So submit like the good slut that you are and give me your twat.”

“You know it is yours to take and use,” she murmured.

With that he started deep, hard thrusts into her already overly sensitive pussy, hitting her clit with each stroke. She gave out a startled yelp with his first stroke and settled into muted moans punctuated by screams each time an orgasm ran from her clit out to her toes. He was determined to give her an extra long and strong session because Greg had been denied seeing this for two weeks.

She could not control her orgasms and she was too weak to loudly vocalize them. She was being reduced to a sweat drenched slut, too exhausted to protest but still being thrilled by each orgasm as it flooded through her body.

Colby was finally ready to cum. He looked at Greg and told him to get ready. He increased the speed of his strokes, quickly bring him to the edge of orgasm. He rolled off Jill and Greg immediately took him in his mouth as the first surge of cum shot into his mouth.

Greg was startled by the force and quantity of his spunk but managed to contain it and swallow just as the second surge hit. The quantity and strength were a bit less so he got it all down and the same with everything that followed. While Colby was pulsing into his mouth, Greg had automatically grabbed the massive black shaft and stroked it to urge the cum from him. He felt Jill’s hot lube covering it, making his movement slippery and smooth. He continued until he had milked every last drop into his eager mouth.

That was a big moment for Greg. He had totally become Jill’s sissy boy, he was changed and could never go back.

Colby pulled himself away, rose to get water and take a shower. Greg was somewhat bewildered and astonished by what he had done; a soaking wet Jill was so exhausted she could not move.

When Colby came back, Jill was sitting on the edge of the bed. “I was about to join you but my legs are still weak.”

He told Greg get the towels off the bed and then go shower in the guest room while he helped Jill shower in the master bath. Greg quietly complied while Colby picked up Jill and took her to the shower where he washed her from head to toe as she sat on the tile bench. He made sure all her parts were fully clean. She just luxuriated in the attention and hot water.

When they came out, Greg was there wearing the nightie Jill had bought for him.

“Greg, you look wonderful in your nightie. Is it comfortable?” Jill asked.

“Oh yes, I like it very much.”

“Well go sleep in the guest room. Jill and I are going to sleep here. Don’t disturb us in the morning. We will come out when we are ready. See you tomorrow,” he said as he closed the door behind the retreating Greg.

“Come on Babe, let’s get some sleep.”

Remaining au naturel, they got in bed and fell asleep; Jill had her head on his shoulder as she drifted off.

In the morning Jill woke around 10 a.m. to find Colby still asleep and his cock sticking straight up, hard as a rock. She could not resist. After a bit of masturbation to start her juices flowing, she carefully climbed on top and slowly descended down his cock. When she was fully pierced, he slowly opened his eyes.

“You little devil! Didn’t you get enough last night?”

“You know I can never get enough of you but I will keep it short and sweet this morning. We both have business to attend to. I have to get ready for that conference I am going to next week and you said you had some business matters that you had to deal with.”

“Sadly that is true enough. Now I want something I did not get last night. I know you just got on me but get off and get on your knees. I want you from behind, in both holes!”

“And you call me a devil,” she said as she complied with his request.

In short time he was holding her hips and time after time stroking deep in her pussy while he repeatedly slapped her ass to a bright red and occasionally reached under her to tweak her nipples.

She squealed with each smack and tweak but each one added to her electrifying excitement and quivering orgasms.

Soon he was repeatedly withdrawing his cock, rubbing it on her ass and going back in for more juice until he had her lube totally coating her ass. When he felt she was ready he withdrew a last time and powerfully pushed into her ass. She screamed from the combined pleasure and pain of first penetration.

With his slow thrusts the pain disappeared, replaced only by pleasure. Once again her orgasms started and he again began slapping her ass in time with his strokes. She could no longer hold herself up; she slid to the bed face down, her whole body shuddering from the powerful orgasms almost continually running through her as he continued to ravage her ass. He followed her down, continuing to fuck her as she lay flat on the bed.

He suddenly stopped, still deep in her, as his cock began to pulse his hot seed into the abyss of her ass. She gave one last shudder and lay as still as him, two bodies locked in the throes of extreme carnal pleasure.

He slowly extricated himself and serenely held her, both silently thinking the same thoughts.

Finally he roused her and they repeated their shower ritual from last night. Then they dressed and emerged to find Greg dressed in his new clothes making breakfast.

“I heard the shower running so I figured you would be out soon. The coffee is ready and the eggs will be soon. Sit and enjoy.”

The three of them had a pleasant breakfast together. Afterwards Colby arose to leave in order to conduct his business. He gave Jill a big hug and kiss, knowing he would not see her for a week. She fully responded, knowing the same thing. Then Greg thanked him for everything from last night and they shook hands. He turned and began walking to the door.

She caught up to him at the door and thanked him for what he did for Greg saying, “When I return I will do anything you want to repay your kindness.”

He smiled, “I am sure I will think of something. Enjoy your week.” With that he was gone.

Jill asked Greg to clean up so she could go work on her presentation for the conference. She was leading a break out session dealing with marketing strategies in the social media world.

Greg told her that after he cleaned up he had analysis work to do on his computer for his current genetic project. She came up to him and gave him a big hug and kiss.

“I love you and was really proud of you last night! You seemed to really enjoy sucking cock and to be able to swallow his cum direct from its source. Did you enjoy it?”

“I admit I did. You have opened a new world to me and I love you for it. These feelings were buried deep and you brought them out. I think I am going to be a better man because of it. I am already feeling more comfortable dealing and interacting with people. I feel a new energy and strength when I put on the panties you bought me. I am ready to go shopping for new and different feminine things I can wear here and secretly.”

“I am glad you are happy and we will do that as soon as I get back from my trip. Let’s get our work done. Tonight I am going to give you more pleasure, so look forward to it.”

“You know I will Sweetie. You’re the best!”

They both went to their studies to work on their projects. They both worked all day, just taking a quick break for a light lunch. Around 5 p.m. Jill opened a bottle of wine and brought a glass to Greg.

“Here Gregie, time to quit and enjoy some relaxation. Let’s have a glass and then go get some pizza.”

“Great idea, I need a break.”

For the first time in quite a while they both asked each other about their work and actually listened with interest to each other. They went for pizza and completely enjoyed their small night out.

When they returned home, Greg was looking forward to Jill fucking him; in fact he could hardly wait. He grabbed her hand and led her to the bedroom.

“I am really dying for another orgasm! Please get your dildo and fuck me. I want to share a cocktail afterwards. What a wonderful word, cocktail. Seems made for us,” he said with a laugh.

She was laughing also as she reminded him that first he had to orally take care of her. He told her he would love that as much as the ass fucking he wanted.

Both were quickly naked; Jill on the bed spread wide for him and Greg ready to dive into her already dripping pussy. He had given her several orgasms when she told him she was ready to pleasure him. He quickly moved to let her off the bed. She used her key to unlock him and took a few minutes to rub his balls and stroke him, trying to prepare him for the maximum pleasure she could give him. When she stopped, he was very erect and begging to be fucked.

He assumed his position as she strapped on the dildo. Coming back to the bed, she handed him a glass and positioned herself behind him. After lubing him and the dildo she began her penetration. His ass opened easier and he only moaned in pleasure. After making sure he was holding the glass properly, she started her thrusts. He immediately began uttering moans and sighs of his thrill and excitement. She could see his cock harden as she drove deep into him.

It did not take long until he gave out a loud cry as his orgasm hit him and his creamy spore began to spurt into the glass.

“Oh fuck! Keep it up. Fuck me deeper. Yes, oh YES!” He reached back to milk himself, wanting every drop to be expelled for his cocktail.

Jill slowly withdrew from him and, after removing the harness, went to make their cocktails. She did not bother with any clothes. She seldom did at night, normally sleeping au naturale.

After returning, she found Greg had relocked himself and put on his nightie. They both sipped their drinks while quietly sitting next to each other in bed. When they finished, she turned out the lights and they drifted off to a good night’s sleep.

After breakfast the next day, Jill began to decide on what to bring to the conference. It was important, both personally and professionally, to make the correct appearance. So she needed conservative with a hint of sexy femininity. Also she wanted some things just in case she decided to go elsewhere at night. Lastly there was the chance that someone interesting would recognize her anklet’s meaning and invite further exploration. She wanted to be ready for that also.

From time to time she saw Greg moving through the house in his skirt and blouse, apparently happy as a clam. She was still amazed by his transformation.

By noon she was satisfied with her selected wardrobe and decided to call the woman Greg had told her about. She found her card, Cathy Wilson. She dialed her cell number and it was quickly answered. She introduced herself to Cathy, telling her that she would be happy to give her the information she wanted but she was curious why she thought the necklace was so interesting.

Cathy asked her why she had given it to Greg. They both danced around the question for a few minutes. Finally Jill asked her directly if her husband was a cuckold. After a short pause she said he was and asked about Greg. Jill also confessed but made her promise to keep Greg’s secret at the University. She totally understood and promised. Jill gave her the information and then suggested that they should have lunch and “compare notes” on their lives. They both agreed to meet after Jill returned from her conference.

The afternoon passed quickly. They both decided to go out for dinner. Greg put on his street clothes over his panties and cami. They enjoyed a nice Italian meal together.

Jill was tired and had an early flight to DC which Greg had to drive her to so they had an early night. Jill quickly fell asleep and Greg read his journals for a bit until he also fell asleep. The alarm went off, jarring them both awake. The new week had started.

They both got ready for their day; Greg in his normal casual work attire over his panties and cami, Jill in jeans and a loose top for easy travel. He dropped her at the airport and continued to work, she caught her plane and arrived in DC mid-morning. The conference was at the Ritz in Pentagon City. She was thankfully able to check in early. After taking care of last minute details with the conference organizers, she rested in the afternoon and went downstairs for dinner. She kept on her tight C. Klein jeans and replaced her top with a white silk top with cap sleeves. Her bra gave her boobs just the look she wanted. Three inch heels finished the look.

She went to the bar for a drink, wearing the ugly conference ID around her neck in case she should happen to meet someone important attending the event. This was a mostly male field so approximately 80% of the attendees were male. She liked it. She was a skillful woman and knew it.

Several men came up and introduced themselves, buying her drinks and mostly talking shop. All trying to be the one who could bring her to their room. She was way too smart for that, especially on the first night, but she enjoyed a wonderful time and dinner, all on someone else’s expense account.

She was intrigued by a very handsome black man who introduced himself amongst all the others. He had very dark skin but his facial features were much more like those of a Caucasian person. “Hi Jill, I am Anthony Washington. My business is in the DC area and I could not resist the conference.”

“A pleasure to meet you Anthony. Maybe I will get to see more of you and we can talk. Unfortunately I am sort of busy now,” she said with a pleasing smile. She noticed him glance at her ankle and smile to himself.

“I will be in the audience for your presentation tomorrow. I am looking forward to it very much. I also hope we get the chance to chat further. I do have a suite here for my convenience.”

With that he left her to the crowd around her. His deep baritone voice and the thought of his glance had sent shivers up her spine.

She had had more to eat and drink than she planned but was happy for all the attention she was receiving. It never hurt to meet people in your field and make a good impression. She finally excused herself and went to her room, she had a big day tomorrow. She fell asleep with thoughts of that deep voice in her mind.

She woke up before the alarm, already jazzed for the day’s event. After breakfast in her room she dressed in a conservative dark business suit over a red silk shell. She looked killer.

She attended the opening session with hundreds in a huge crowed room. It was basically a welcome session. After a short break her session would start. Ninety minutes of what she hoped would be picture perfect and very well received.

That, in fact, is exactly what happened. Her nerves disappeared, her presentation received much applause at the end and the Q & A session brought out many useful ideas. All in all it was a terrific success.

She saw Anthony in the group around her that was trying to ask more questions. He simply handed her a small note card and left. She put it in her pocket unread, too busy handing out her business cards and trying to answer questions before they were all chased out of the room.

Finally at lunch she had a chance to read Anthony’s note. “Wonderful presentation, congrats! Love your anklet, see you at the bar tonight.” That same shivers briefly hit her. What would happen? She knew she could do nothing but see it through, she was hooked.

Soon the day was over and cocktail hour had arrived. She wanted to look sexy but not too much so; business like but not stuffy. She settled on a straight black skirt, shorter than normal but not slutty. A matching, form fitting jacket, over a lower cut red cami and a push up bra that put some of her cleavage on display. Four inch heels this time. Lastly she relotioned her legs to give them a perfect shine.

When she arrived at the bar, all the seats were taken. Several guys offered theirs and she gratefully took one. She soon had drinks and was surrounded. Once again, life was good.

After about forty-five minutes Anthony showed up at the bar. He is a big, commanding man and his voice adds to his presence. He excused himself as he easily moved through the crowd and hand Jill another note.

He whispered to her, “Read it out of the crowd’s sight. I will be on the other side of the bar. Make eye contact with me and nod if it interests you.” He turned and made his way back through the crowd of guys.

Jill waited a few minutes to discourage prying eyes and then read the note while holding it down so only she could read it. “Jill, your anklet tells me that you are a BBC slut. If I am correct and you want to play, I am your guy. If we make eye contact and you nod to me I will expect you to come to my room, 1205, as soon as you can get away. Stop and remove your bra and panties before you come to my room. I look forward to our evening together.”

She had acquired that anklet for this very reason. His low-key manner and deep voice sealed the deal for her. As another shiver ran down her back she looked up and saw him, eye to eye. She gave a small nod and looked away to a guy who was talking to her.

She could feel the heat building in her pussy and her juice beginning to develop. It was very hard to pay attention to the guys talking to her but she did for several minutes. Unable to wait longer, excused herself saying that she would see them later and headed for her room.

Once in the room she quickly removed her panties and her dress jacket. After unhooking her bra she pulled the straps free of her arms and pulled the bra down and out. Looking in the mirror her nipples were quite visible through the silk top. Her firm breasts looked terrific so she left the jacket off and departed for his room.

A short elevator ride later she was knocking on his door. He promptly opened it and invited her in. He was wearing only a white silk robe.

“Jill, I am so glad we connected. I admire you very much for your professional skills and the choice you made by wearing your beautiful anklet. Please come see my small suite.”

“I appreciate the complement. Thank you for noticing me and my anklet. You are not wrong about its symbology.”

The room quickly opened to a living-dining area with a small bar and a door that had to lead to a bedroom. He took a seat at the bar and turned to face her, his back to the bar.

“Come here and let me get a really good look at how beautiful you are.” His deep baritone voice seeming to reverberate through the room.

She kept glancing between his legs, catching quick glimpses of his obviously large black organ. She was hoping he would display it more but it was mostly covered by the robe and he made no move to open it.

“You look stunning it that red silk cami. It shows off your nipples magnificently!”

As she stepped even closer to him she never really saw his hands move but suddenly each of his hands had one of her nipples in a firm grip between his thumbs and forefingers. She gasped and he applied even more pressure.

“I love the feel of your tits between my fingers. It is sort of a pain pleasure feeling isn’t it?” He asked her as he pulled her even closer.

Rapidly recovering from the shock, she replied, “Yes, it is like that. Part of me wants you to stop and part wants it to continue.”

He applied even more pressure while slowly rolling them in his grip. The effect could be seen in her eyes.

“Have you ever had nipple clamps or continuous pressure this strong applied to your nipples before?”

“N... No.”

“Soon it will fade as your nipples become numb from the blood supply being cut off. You will only feel mild, maybe somewhat pleasant pressure.” He rolled them a bit more and her reaction was less, they were numbing.

“Now tell Big Daddy why you are here and what you are.”

He held her only inches from him and in a way that she could hardly move. Motion on her part would only stretch her nipples and probably hurt more than the relatively mild pain she now felt.

“I am a BBC slut and I want you to use and fuck me in any way you desire. I crave your cock and badly need it.”

“Reach down and feel it. Fondle it. Show it your love. Tell Big Daddy how it makes you feel.”

She did. It was thicker than any she had known but not very long. It was about like Colby in length but quite thicker.

“Oh Anthony it is wonderful! It is so thick. I have never felt one like this. It will stretch me farther than I have ever known. Its length is perfect. I know I can take it all. I feel your veins and its spectacular head. I want to suck it and be fucked for as long as you want me.”

She had completely forgotten her tightly pinched nipples as she was enthralled by his beautiful cock. It’s bewitching feel and size and totally captured her senses. She was dreaming of what she hoped was the not very distant future.

“Thank you my dear. I believe you truly are a BBC slut. I am soon going to release your nipples and you will undress for me but before I do, since this is your first experience with tight nipple clamping, I need to inform you what you will feel next.”

“When I release you, your blood will rush back into your tits and enervate your numb nerves. For a very brief period the pain will be fairly excruciating as the nerves come back to life. I advise you to massage your nipples as this happens, it will lessen the pain and shorten the recovery pain. Ready?”
As Jill was taking all this in, he released her. “God damn! That fuckin hurts! Shit, shit!”

She reflexively began to massage them and the pain quickly diminished.

“Now be a good slut and slowly turn in those beautiful heels as you remove your remaining clothes.”

“Okay Anthony.”

“That is ‘Yes Big Daddy’ for the night.”

“Yes Big Daddy,” Jill replied as she dropped her skirt and removed her blouse, leaving her in only her heels.

“You are a true vision of loveliness my dear. Get over here on your knees and show Big Daddy your oral skills and BBC love.”

Jill did not give a thought to the submissive role she was beginning to play due to her overwhelming desire for his cock. She quickly and hungrily pulled the giant organ to her mouth, took it in and began licking, sucking, kissing, caressing and fondling it.

Big Daddy just leaned back and sipped his drink. He had been down this road before and knew how it would end. He could play her like a violin.

Jill could not stop herself if she even thought about it. She was totally entranced by its color, size, texture and her own desires.

He finally reached down, grabbed her hair and pulled her up to him. She was somewhat out of breath from holding it in to suck him better. He cupped her boobs in his hands, gently rubbing her nipples and held her in a long kiss.

“I think it is time we got that in you, what do you think?”

“Oh my god YES! Take me Big Daddy!”

He eased off the stool, took her hand and led her to the bedroom. He let her go and she quickly climbed on the bed, spreading her legs for him.

“I love your enthusiasm and desire but first you need to put these on.”

He tossed her leather wrist and ankle cuffs. She gave him a questioning look, which he expected.

“I need to tie you to the bed or you might lose total control. Tonight will be like nothing you have experienced so far in your life. Just trust me in this.”
With her pussy throbbing and juice running down her thighs, she rapidly complied. He in turn produced rope that he used to tie her tightly, spread wide on the bed. Only then did he climb between her open legs and fully exposed coochie.

It began with him slowly and mildly slapping her clit with his cock. She jerked and squealed with every smack. As the blows became harder and faster she began to cum.

“Oh yes, now, I am cumming! Keep it up. Do me more. Cumming! Damn, damn again!”

He had not even entered her and she was already having multiple orgasms. She is going to be a tiger he thought as he continued the slapping and she continued screaming and yelling.

When she was beginning to gasp for breath he stopped and began rubbing his cock’s head up and down her slit. Running across her clit on each movement. He was dripping with her juice when he first began to enter her snatch.

“Fuck! It is so fucking big! Damn. Just give it to me. Do me, do me.”

With steady even pressure his cock went fully in on the first push. Seeing her legs and arms jerking and yanking at the ropes from the slapping he knew he had made the right decision about tying her to the bed.

“Oh my fuckin god! I as SO stretched and stuffed. Fuck me, just fuck me!”

As with the slapping, he started slowly. Each stroke was slow but deep. He gradually increased his speed and her orgasms followed his speed. She was gasping for air. Her body was quivering with each orgasm and almost constantly thrashing on the bed. She strained against the restraints; was no longer able to form complete words. Her sounds were loud moans and incoherent parts of words.

Anthony was loving this. He was in complete control of this woman. She had totally lost her senses from his fucking. He sped up, he slowed down, every action provoked a different reaction from her. He used her for his pleasure, loving her hot, slippery pussy tightly wrapped around his huge cock. Loving her juice squiring out, over and around his cock every time she climaxed.

She had had many orgasms by this point and could no longer utter any understandable words. She was squirting her pussy essence with every climax, not to mention the sweat running down and off her body. Her breath was coming in pants and gulps. Her legs and arms were constantly pulling against the rope; her muscles trembling and quivering. Jill had lost herself in her own carnal, sensual, exhilarating world of erotic lust.

He kept this up for way more than thirty minutes but finally he could feel his orgasm building. The stronger his feeling the faster he pumped her. She was squealed as the first pulse of his hot seed shot deep into her cooch. His pulsing continued as did her squealing until he had left his last drop in her. He slowly pulled out and she did not move. She gasped and gulped for air as her heart beat slowly returned to normal. Her brain slowly left her land of lust and returned her to reality. She eventually opened her eyes, still completely unable to move.

“My god what happened. What did you do to me? Even now I could not move even if I was not tied. Please release me and get me water. This was absolutely unbelievable!”

He quickly released her, sat her up in bed and gave her a liter bottle of water to drink from. As she drank, his massive deposit of seed began running out of her. At first it was a flow which then slowed to a trickle, all puddling between her legs.

“I believe there is something between your legs that you need to clean up. Enjoy every drop. The night is still young my lovely slut and I am far from through with you...”

******

To Be Continued