Date Night 44

Mary had no luck with men. She was a very pretty petite blonde with a perpetually sunny smile and disposition. Yet all the men she was meeting were some mixture of arrogant, horny, desperate, and/or clueless about how to act on a date or around a woman. The worst of these was the horniness. You want men to have a healthy interest; but the guys she dated almost universally either would start pressuring her to have sex, or were so clearly worried about the question of getting into her pants as soon as possible that they were almost incapable of normal conversation.

One day she was about ready to give up and become a twenty-something year old cat lady when she was talking to one of her coffee mates about this perpetual problem. Her friend mentioned a new concept in dating services that she had just heard was starting up. Very low key and private. The idea was to get the sex out of the way first in a setting that would not be threatening to the woman, and would alleviate some of the arrogance and other bad behaviour of the man. This sounded intriguing to Mary although there were few details about the specifics. But she got the number and resolved to at least call them up and ask some questions.

Rob was a man having similar bad luck on the dating treadmill. He meant well, he really, really did. He was normally a nice guy and even a little shy. But on a date he inevitably started obsessing about whether he was going to get lucky. He couldn't pretend to himself that he didn't care, because he really did, and the more he tried to pretend he didn't the more he did, so that didn't work. He couldn't stick to a pledge to himself not to not have sex on the first date, because even though it had never happened to him he knew that sometimes it did happen to other people and that there were women out there that were horny enough and seemed to expect it and he was worried about disappointing a woman if she did expect it and didn't get any. Which would be so frustrating for him considering that he wanted to but was worried that she wouldn't and so he wouldn't push it. And so on and so on. It was so much easier to stay home and watch TV.

Then Rob heard about this new dating service, based on an interesting concept and just starting up. Apparently the idea was that they would have the sex first and get it out of the way, so everyone could relax and get to know each other in a more relaxed environment afterwards. Of course this got his attention, and while he didn't get many details at first, he did manage to get the phone number of the service and he too was determined to call them the next day.

He spoke to a woman there and was told to come in later the same day if he wanted to have an initial interview right away, if it was convenient. The thought of guaranteed sex made the prospect seem very convenient indeed, and Rob found himself in their offices at 7 p.m. that evening.

A woman named Amanda spoke with him at length and asked him questions about himself, his past experiences with women, and what he was looking for. Finally, she began to explain more details about the sex component of the service.

The whole idea she said was to provide a safe and non-threatening environment for the women while at the same time defusing all the tension around the question of the possibility of sex. The sexual interaction was structured totally around these objectives and was not for the purpose of gratifying the men at all. After all, men really didn't need very much help to achieve their own gratification from any kind of sex whatsoever.

She first had him sign a rather extensive and quite thorough non-disclosure agreement that guaranteed that if he revealed anything of the procedures then he might as well just leave his testicles on the desk on his way out the door. She then went on to explain the details of the encounters, some of which were rather bizarre. Rob was stupefied at first, and started yelling and refusing to participate. Amanda calmly and patiently outlined the reasoning and the advantages of their methods and compared them to his usual disasters. In the end his growing and eventually rampant horniness led him to agree to everything. Amanda smiled at him and had him sign several release forms and other paperwork before accepting his cheque for the agency's services. When they were done, she said that if he wished he could start the first date right away. Rob by this time was once again horny and eager to start, although with a lot of trepidation, and agreed.

She led him into a room with a large frilly four poster bed as well as some armchairs, a big wooden table, a sink, and some clinical looking apparatus. There were five women sitting around the room sipping drinks and chatting. They seemed remarkably relaxed for a date evening; but of course this wasn't a normal date, and their relaxation was the whole point.

Amanda introduced them all, including Mary who happened to be in the group that evening, asking the women to tell a little about themselves and asking Rob to tell a lot about himself. Then she asked Rob, who was still standing, to strip and display himself to all the women.

Everyone had known this was coming, but Rob still turned bright red as he peeled off the last of his clothes and stood before them stark naked. Amanda then told him to slowly turn to give them all a good look at him, and to then face them and start to masturbate himself.

Amanda started a movie camera on a tripod already set up in front of the room, and gave another handheld to Susan so they could get a record of Rob's adventures aver the course of the evening. Knowing he was being filmed did nothing to ease Rob's discomfort.

After the room had been quiet as they all watched Rob naked and masturbating for them for a couple of minutes Amanda started a patter about Rob and what he was going to do for them. She asked each woman in turn what she thought about aspects of his physical appearance and his performance so far. In doing so she was beginning a deliberate process of objectifying him. She wanted them to get comfortable with the idea of using him for sex, rather than worrying about his feelings and holding back how they treated him. At one point she referred to him as the fuckmeat, and as a support system for a cock. And for a tongue.

Before he got too far along the road to orgasm (which was happening in spite of his humiliation) Amanda told him to stop and announced that it was time to get him cleaned up and out for the next phase of the "date". This was to be a group participation exercise.

Rob was laid down on a plastic sheet on the bed on his stomach with his legs spread. A rack was brought over with an enema apparatus and two of the women held him in place as another filled the bag with warm soapy water. Rob himself had to lubricate his own asshole in front of the others. He was given a large bottle of water soluble lubricant and told to thoroughly grease himself up inside and out. This was extremely embarrassing but he reluctantly did it, mindful of the pain he was about to experience.

Sarah slowly and carefully inserted the lubricated nozzle into his rectum and then the water was released, again very slowly. They gave him a full two liters, massaging his stomach and sides and pretty much ignoring his discomfort and sometimes even laughing at his escalating complaints. The last of the water trickled into him just as he was on the verge of tears and starting to beg for mercy.

They made him hold it for five minutes and then allowed him to stiffly waddle across the room over to a small commode that was in the corner, where he had to sit down in front of the women and expel the murky mixture from his bowels. He then had to move over to a bidet right next to it and wash himself on it for the first time in his life. It was awkward and embarrassing learning how to use it by trial and error in full view of the others, with them laughing and joking while sipping their drinks and poking fun at him.

He had to repeat the enema process two more times before he was deemed clean enough to fuck. He bent over the edge of the wooden table where there were pads on the edge, and was told to again lubricate his asshole in front of everyone, this time inserting the nozzle of the lube bottle right into himself and squirting a large quantity inside. After he finished spreading it in his hole and all around the outside he reached back and pulled his asscheeks apart and then just lay there waiting for them to start.

Amanda distributed strap-on cocks and harnesses to everyone. Women got to choose whatever size cock they wanted to use but were told that the first to fuck him had to use the smallest as the first would give him the most pain. Finally they were ready to start. Amanda said that everyone had to wet their cock by inserting it into Rob's mouth and getting him to suck a little cock for a bit before they fucked him with it. Judy, who was first, slid her cock into his mouth and initiated his cocksucking career. She encouraged him to take it as deep as possible but he couldn't stand to take it into his throat, so she let up on him and moved around back. She touched the cock to his anus and started slowly and gently pressing it against him, telling him to relax and just let it sink in. She was gentle at this point and went very slowly, and the cock was pretty small, so eventually she had it in him with relatively little pain.

She let him get used to it for a while before she moved at all. Even then she started with just short, slow strokes. She did this for a long time before she started pulling out further and going in deeper. But finally she had him fairly relaxed and used to it, and that is when she started really fucking him. With all the lube inside and more being dripped on from outside he didn't really feel much friction and so she felt freer to plunge all the way in and out. She started banging him harder and faster, trying to put repetitive pressure on her own pelvis through her clothes. The rule was that nobody stopped until they came, no matter what he said or even if he cried.

In the meantime, once Judy had completely "bottomed" out in his ass for the first time, he was told to grab his cock and start to masturbate. Judy would be able to bang him with enough force to get in deep enough without him holding himself, and it would give her more pushback.

Amanda told everyone that it was important that Rob experience an orgasm while his sphincter was clenching down on the hard cock in his ass; both to loosen him up for the larger cocks he was going to get in the future; and so that he would learn to experience anal orgasms as part of his training.

Once Judy finally had her orgasm Amanda told her to pull the cock out of Rob's ass and put it directly into his mouth so that he could clean it completely, licking and swallowing all the fluids from his own ass in front of everyone.

After all five of the dates had fucked Rob and cum, Amanda announced that they had one more optional activity – each woman could choose to have Rob eat her pussy if she liked. Since the evening had pretty much devolved into a sort of wild girls' night out party atmosphere and there had been a fair bit of wine involved, everyone enthusiastically agreed that they wanted some. So one by one they all lay down on the bed, removed their slacks, and let Rob go to work getting them all off once more. Inhibitions were so completely gone by this point that the orgasms were fast and very satisfying and accompanied by much laughter from everyone.

During the evening everyone had talked about themselves with everyone else and even with Rob, so that at the end of it all he knew something of them and once the rest had left was invited to tell Amanda whether he would like a second date with any one of them. Although the women had been artificially dominant according to the script, it was important that Rob actively chose one or more he liked; and similarly each one of the women were privately asked if they would be interested in seeing him again. This would be another supervised date, but would be more of the conventional dinner and conversation. He could choose as many as he liked, but was encouraged to date one at a time. In this case he decided he wanted to get to know Mary a little better, and chose to have a "normal" date with her. Fortunately she also indicated that she would like to meet with him again.

For whatever reason, his choice worked out. He and Mary enjoyed a simple dinner in the company of a staffer from the service, so once again sex was not on the agenda and there was no pressue on either one of them about that. They continued to see each other after that, eventually getting married and raising a family.

Every so often Mary would ship the kids off for an evening and invite one or more of the other women from the date night over, where they would all have great times talking and fucking Rob just like they used to. Over the years the others got partners as well and they came along for the fun. Rob would be strapped across the table and everyone, men and women, would take turns fucking his ass and getting him to suck their pussies and cocks. They lived long happy lives and their marriage was the envy of their friends and family.