A First Time For Anything

by Pamela

pamelapamela@hotmail.com

 

"Gregory? Gregory Musco? Is that you?"

Gregory froze in place and turned to see Janet May smiling broadly at him. It took just a second for Gregory to remember who she was. They had met a few months earlier at the company summer picnic that had been hosted by Janet and her husband, William, who was Gregory's boss at the investment bank.

"Oh hello, Mrs. May" Gregory said with surprise as he hurriedly put the fancy pink girdle whose size he had been checking back into its place in the rack in front of him. They were standing in the lingerie section of a Macy's department store located almost fifty miles from where they lived and where Gregory worked for Mr. May.

"Call me Janet. Such a surprise when you run into someone you know so far from home," Janet said gaily.

"Yeah, that's certainly true," Gregory said, hoping that Janet was not going to ask him about the girdle.

"Doing your Christmas shopping?" Janet asked.

"Yes," Gregory lied, "and you?"

"Not quite yet, Thanksgiving is next week and I like to wait until after the holiday is over."

"Yeah, I suppose that's a good idea."

"I just had lunch with my eldest daughter, you know she's the manager of cosmetics on the floor below, and I thought I'd come up here and check out the bra sales," Janet said.

"Really? That's interesting, I mean about your daughter," Gregory said with obvious embarrassment and Janet laughed.

"Bill is off playing golf, taking advantage of the Indian summer. Do you golf?"

"Oh, no, I never developed a taste for it though I tried a few times."

"Well I guess that does free you up for some early Christmas shopping on the weekends." Janet chuckled softly to herself. "Isn't it kind of a journey for you to come this far to shop?" They both knew that there was a much closer Macy's in the mall just outside of town.

"I like the drive, and actually I think this Macy's is bigger than the one in town. More selection."

"More girdles?"

Gregory blushed. "Oh, that? No. I just happened by, and actually its funny but last night I saw this great old movie "Operation Petticoat" with Cary Grant and there's this scene where they use a girdle to fix the bilge pump or something. I was curious about how strong girdles actually are."

Janet let out a belly laugh and then controlled herself. "That's funny, Gregory. I thought maybe you were going to buy one as a present for your mom or more likely your grandmother. Not too many young women wear girdles nowadays. Though they are pretty retro and some girls might like them for that."

"I see what you mean. They must be awfully uncomfortable to wear, I mean for women." Gregory said feeling foolish.

"You can't imagine! And you have to wear stockings with them so it's a procedure to fasten them up on the garters."

Gregory was now beet red. Janet was relaxed and looked as if she was in no hurry to leave. She reached in front of Gregory and took the very same girdle Gregory had been examining off the rack, and held it up with two hands to take a good look at it. "My this is a pretty one, and unusual both for being pink, which many girls are not crazy about nowadays, but also because of the exquisitely fine lace. My goodness, its also 94 dollars. Must be imported from France!"

"I guess it's plenty flexible."

Janet looked at him wryly and then said, "oh, yes, I see, in case you need it for a bilge pump."

"Yes exactly," Gregory said making a weak attempt at humor. Though considerably older than himself, he couldn't help but marvel at Janet's good natured and youthful personality.

There was a momentary silence and Gregory said, "well I guess I better mosey along. It's been great seeing you and give my best to Mr. May. I suppose I'll be seeing him on Monday."

Janet smiled at him and said, "good luck with the rest of your Christmas shopping!"

"Thank you," Gregory said and walked away. When he got to the escalator he turned around to look back and saw Janet standing where he had left her. She waved at him and he returned the wave. They continued to look at each other until the escalator carried Gregory out of view.

When he was outside the store Gregory decided he had better go directly home and give up the idea, at least for this weekend, of buying his coveted girdle. Wearing a girdle was something he had longed to do for many years, but he had never until this day had the nerve to even go to a lingerie department let alone select a girdle to buy. The trip had been a sudden inspiration. Jump in the car, drive 50 miles away, no one would know him, do everything without thinking. Thinking of the consequences was what had always stymied him in the past.

It was ironic that his plan had worked so well only to be thwarted near the very end by the chance encounter with Mrs. May. He had been so elated to find the lingerie department virtually deserted. It had taken only a moment before he noticed the rack of beautiful sexy pink girdles. He had just to find one of a size he'd be able to squeeze into. The ones at the front of the display had seemed too small for him and he had reached further in the row and had just pulled out a larger one when Janet had appeared. So close yet so far: the only other hurdle would have been the saleslady, but she looked to be a bit spaced out and he doubted that she would care too much about who was or wasn't buying ladies underwear. Alas, now he would have to await until another day before he felt bold enough to make another try.

A more immediate worry that occupied Gregory on the drive home was guessing what Janet might say to her husband about finding Gregory holding a girdle in the lingerie department of Macy's fifty miles from home. His explanation that he was satisfying his scientific curiosity aroused by "Operation Petticoat" was utterly ridiculous; Mr. and Mrs. May were certain to suspect his interest in cross dressing. But, after all, it was a free country and he didn't see any reason why the incident should affect his situation at the company.

 

 

Over the rest of the weekend and into Monday morning Gregory did the best he could to try and forget about the bizarre incident with Janet May. He spent a productive morning working on his accounts and broke for lunch with the usual crowd at the local deli. After lunch Gregory saw that a note had been placed on the desk in his cubicle saying that Mr. May wanted to see him in his office. While not unusual, such requests were infrequent, so Gregory had some trepidation as to what it could be that Mr. May wanted to see him about it. Even if his wife had told him about the compromising position she had found him in, so what? Why would that be of any real interest to Mr. May?

Gregory took the elevator up to the penthouse floor where the governing executives had their suites. Mr. May's secretary buzzed her boss to let him know that Gregory was waiting and in short order Mr. May came to the door to welcome Gregory and usher him in. Mr. May was all smiles, in fact Gregory could not remember ever seeing him in such a festive mood.

"Have a seat my good man," Mr. May said, offering Gregory one of the large chairs facing his desk.

Gregory was happy to oblige; it seemed like he was about to receive kudos for one of his astute investment decisions and the possibility of a quick promotion or bonus crossed his mind. His excitement suddenly waned when he saw three neatly stacked gift boxes from Macy's department store lying on the otherwise bare desk in front of him.

Gregory tried to smile at Mr. May while he watched him take his seat behind the desk. "Would you like coffee or tea?" Mr. May asked.

"Oh no thank you, Mr. May, I'm just back from lunch."

"Of course. You're probably wondering why I called you in today. Let me cut right to the chase. I've learned through Mrs. May, or should I say Janet, of a certain interest or perhaps one could call it fascination you have with certain clothing that tends to be worn by the ladies...so...I, we decided to ..." Mr. May paused for a long moment and Gregory felt himself sweating. "I don't know how to phrase this. Let me just say I have these three presents for you from Janet." He pointed to the boxes from Macy's.

"Presents?" Gregory asked nervously.

"Yes, gifts that I hope you'll like. Actually, Janet and I both hope that you like them."

"I don't know what Mrs. May may have told you about Saturday," Gregory said in alarm, "but..."

"No need for drama, Gregory," Mr. May said cutting him off. "Please accept these gifts."

Gregory stared at Mr. May for half a minute and then took the top box and put it in his lap.

"Go ahead and open it," Mr. May said.

Having a pretty good idea what was inside Gregory reluctantly opened the box. Delicately wrapped in pink tissue paper was the very same girdle he had been holding when Janet May had seen him. "A girdle?" Gregory said.

"Janet says you were more than likely going to purchase it, except that she interrupted you and probably caused you some embarrassment."

"I told her why I was looking at it."

"Oh, yes, "Operation Petticoat," a great film but really Gregory, you surely don't expect anyone to believe that you were testing the elasticity of girdle fabric?" Mr. May chuckled to himself. "Janet is a pretty good judge of people and motives and I know she won't feel right until she knows that you've accepted these gifts. Go ahead and open the other boxes."

With beads of sweat on his forehead Gregory took the second box and opened it. It was very light and inside was a pair of flesh colored stockings with a band of lace at the top. "Stockings?" Greg said.

"To go with your girdle," Mr. May said helpfully.

"Mr. May, I feel like I'm being made fun of."

"Open the third box, Janet says it matches."

Gregory opened the box to find a beautiful pink bra that was a close if not perfect match in color and lace design to the girdle. "It's a bra."

"I can see that," Mr. May said. "Janet wants to know if it fits. If not she'll take it back and exchange it. She says it's not easy to figure out what girls' sizes would fit a man, particularly due to the thicker waists and shoulders that men tend to have."

"I guess it would fit. The bra and girdle both look to be large enough."

"Would you try them on, just to make sure?"

"Try them on? How could I possibly do that?"

"It's easy. Go over to the alcove," Mr. May said pointing to a shallow alcove at the far wall of the large office.

"No offense intended Mr. May but you have got to be kidding, aren't you?"

"Gregory, I'm not offended. Trying on lingerie in your bosses office must certainly seem to be out of the ordinary, but please allow for the special circumstances. Janet feels bad that she embarrassed you and this is her way of making it up to you. She really wants to know that everything fits. If not, she'll make the exchange."

"I could do that myself," Mr. May.

"No, no, no. Janet visits our daughter quite often and it would be easy for her to make the exchange, if it's needed."

"I don't know what to say Mr. May. There won't be any consequences for me at the firm?"

"Of course not Gregory, but if you keep up that kind of talk you will offend me."

Gregory looked carefully at Mr. May's face for any sign of insincerity and finding none decided that maybe his best course of action was just to acquiesce. Try on the clothing and see if it fits. A pretty straightforward exercise.

Gregory walked to the alcove carrying the 3 boxes and their contents. "You mean change clothes right here?"

"Yes, right there. I won't look if that makes you feel more comfortable."

Mr. May gazed at Gregory quizzically as if wondering what in the world the problem could be. Fighting against his instinct that what he was being asked to do was wrong Gregory accepted that maybe his boss knew better: that he was being overly paranoid or proper. He then found himself taking off his shoes, unbuckling his belt, and slipping his pants down to his ankles and then off. Glancing up at Mr. May he saw that he was now sitting at his desk engrossed in reading a document. Gregory turned his back to Mr. May pulled off his underpants and held up the girdle to see how he should put it on. It looked a bit like pink bike shorts but with lace and attached garters at the leg openings. He stepped into it and pulled it up. It was snug but fit reasonably well over his behind. It did flatten his tummy a bit but then again at his age he didn't really have a belly that needed to be flattened.

If he were home or anywhere else except in the presence of Mr. May he knew that he would be feeling some sort of ecstasy just about now. Even in this setting, wearing the girdle made him feel more than a little feminine, and he could tell that it was going to require some inner discipline to not lose control of himself. Happily, the girdle was a present to him so he would be able to wear it in the future, maybe even that night, without Mr. May in the room.

Gregory leaned against the wall and gently put one of the stockings on over his left foot and carefully pulled it up to his thigh. It was a procedure he had often envisaged doing, so that actually doing it seemed almost natural. A slight further pull and Gregory joined the top of the stocking with the garter and clipped it into place: first the front garter than the rear one. He felt a bit faint with excitement. The reality was better than he had ever imagined it would be. His mind thought of the millions of women walking about at this very moment wearing girdles holding up their stockings. Well, maybe it wasn't that many women considering most wore pantyhose. Regardless of how many there were, he fantasized that he was one of them himself now. He was now a sort of honorary member of the sisterhood.

Gregory put on the second stocking and as he was attaching the garters Mr. May said, "How are we coming along Gregory?"

"OK, Mr. May."

"Does your girdle fit?"

"Yes, I think it does."

"Not too tight?"

"No, it's comfortable; I mean it fits just fine. Look, do you want me to also put on the bra? Is that what you want to check also?"

"Yes, Gregory, Janet took a wild guess as to what your size might be. You need to check it out."

With the girdle and stockings now on, Gregory felt almost delirious and even bold enough to not care where this strange experience might lead. Considering how happy he felt, how could it be wrong? He took his shirt and undershirt off and then took the bra out of its box and thought about how he would put it on. It was exactly the kind of bra he had imagined getting one day - well that was a no brainer. He knew he wanted the most feminine of clothing - clothing that would match some inner girl inside himself. A girl who had first intimated her existence in him when he was 12 years old, but had been forcefully banished every time she had tried to appear for the last dozen years. In his minds eye he had also rehearsed how he would put on a bra and he did so easily and quickly. He shyly walked over to stand in front of Mr. May's desk. Gregory saw that Mr. May was busily penciling comments into the margins of an accounting report in a blue folder.

"I guess I'm dressed Mr. May," Gregory said quietly, afraid to interrupt him.

"Just a second Gregory," Mr. May said without looking up. After a minute he put down his pencil and gazed up at Gregory. He laughed slightly and said, "such an interesting blend of the male and female, I'm sorry for seeing the humor in it. Yes it seems that Janet has done very well sizing you up."

"Can I take the clothes off now?" Gregory said, feeling a surge of embarrassment after Mr. May's laugh. Maybe there was going to be damage to his career on account of this, after all. Every time Mr. May saw him in the future he might think of this image and laugh again. And would he and Janet share a laugh at his expense tonight?

Before Mr. May could answer Gregory the phone on his desk rang and he picked up the receiver. "Yes Sherri ... the delegation is here ... outside the door ... OK, we can't keep them waiting."

"Gregory. I'm afraid the Japanese delegation from Kyoto has arrived. It's an important meeting. You can't be in the room dressed like that."

"I'll change back!"

"There's no time. Here, get under my desk, there's plenty of room."

"What? Spend the meeting crouched under the desk?"

"It's spacious, don't worry and it won't be too long. Quick!"

Caught off guard and confused Gregory climbed underneath Mr. May's huge walnut desk while Mr. May got up and gathered Gregory's clothes and put them in a drawer.

"Can I have my clothes, Mr. May?" Gregory said.

"No time!" Mr. May said as Gregory heard him open the office door and loudly welcome the group. "Hello, Mr. Kawasagi-san, Mr. Yamamoto-san and Mr. Sato-San."

Gregory saw that there was more than enough room to stretch out under the large desk. He heard the Japanese return the greeting to Mr. May, who offered them coffee and tea. Mr. May sat down at his desk in front of Gregory and buzzed his secretary to bring coffee. Gregory guessed the Japanese were taking seats facing Mr. May's desk. Mr. May slid his chair up to the desk and Gregory had to move back as far as he could to avoid touching his legs. From his vantage point Gregory had an easy view of Mr. May's lap and knees. This was definitely going to be a long afternoon unless the meeting was very brief.

After coffee was brought in, Gregory could hear a discussion about financing of a new American venture for the Japanese company. The amount of money was huge and a step up in size from the normal accounts of the investment firm. It perhaps explained Mr. May's rush not to keep the Japanese waiting so as to give Gregory an opportunity to leave. Anyway, it was certainly important that he kept hidden lest he jeopardize the deal in any way. Popping out from under the desk wearing a girdle and bra was not probably something the visitors expected from a company they were thinking of doing business with. Of course, it was Mr. May who had created such a precarious situation in the first place.

Ten or fifteen minutes into the meeting it sounded to Gregory as if everything was going very well. Despite his awkward position under the desk, Gregory nevertheless took advantage of the opportunity to admire the pretty clothes he was wearing. He had never worn a bra before and he had to admit it was a pretty wonderful experience. Of course, the feeling of the girdle and stockings was sublime and all in all he supposed he ought not to complain about his fate. While lost in these thoughts Gregory noticed that Mr. May had slid his right hand into his lap and to his astonishment was fondling himself through his pants. Even more surprising he pulled down the zipper to his fly and put his hand inside his pants. Clearly he must have forgotten that Gregory could see everything. It was amazing the things you could learn about a person when they thought they weren't being watched.

After a short while, as the conversation droned on above him, Gregory saw Mr. May's hand fumbling around inside his pants and the next thing he knew he had pulled out his member. Apparently, it had responded to the incessant massaging through his pants by becoming almost fully erect. Gregory tried to twist around in such a way that he couldn't see the penis even if he wanted to, but it wasn't possible unless he was willing to have his face jammed up against the underside of the desk. Gregory closed his eyes and shook his head in amazement. What a weird predicament to be in. Surely Mr. May must know that Gregory could see everything he was doing. It made Gregory wonder about what had been going on at the many company meetings he had been at during the year. Had Mr. May been playing with himself under the table all the time? Talk about who should be embarrassed, Gregory thought. As much as I may be wearing ladies underwear, Mr. May is even more bizarre.

Mr. May was now stroking his member in a more or less rhythmical pattern and it had gotten fully extended. It pretty much filled all of Gregory's vision when he opened his eyes. Mr. May's hand accidentally bumped into Gregory's jaw, so that Gregory realized that Mr. May could not, at least now, have forgotten that he was inside the desk. Gregory heard Mr. May tell a joke and the Japanese men laughed. Mr. May's ability to talk business, entertain and beat off at the same time was pretty extraordinary Gregory thought. It was a talent that probably well equipped him to be a manager. A few minutes later Mr. May seemed to slow his rubbing and his hand moved away. The cock withdrew a bit from its erection and sagged a little. A minute later the hand reappeared holding a yellow post-it note which, after groping around, stuck it onto Gregory's face next to his nose. Gregory angrily took the note off his face and read it in the dim light. It said, "come help me out."

Gregory looked and saw that Mr. May was once again touching himself with his hand. Gregory felt a ripple of anxiety course through his body. Did Mr. May want him to help massage his cock? How could he possibly touch the thing? Mr. May had now definitely gone past any reasonable boss/worker boundary.

Gregory made a derisive face in the dark. There was clearly no way he was going to touch that thing. After a few minutes he felt Mr. May tapping him on the shoulder and point toward his dick. A minute later a second post-it note appeared saying, "please join in." Mr. May was obviously trying to be polite about the whole thing, but still, what he was asking couldn't possibly be justified. Gregory squirmed looking to see how he could get out of the predicament he was in until he felt Mr. May firmly touch his shoulder. There was something quite commanding about the touch: forceful without hurting, it seemed to be telling him that he was losing patience and that Gregory had better do what was expected of him. Clearly Mr. May wanted him to help him masturbate. Imagine that, helping your boss to beat off during an important international meeting!

The hand disappeared and came back with another note: "I'm waiting Gregory. I expect help." Gregory thought of leaping out from under the desk and telling the Japanese what was going on underneath it, but of course, considering how he was dressed, that didn't seem like a particularly smart course of action. He now felt a sharp tap from Mr. May and Gregory thought, OK, I'll touch the bloody thing a little just to save my job and keep Mr. May from bothering me. Gregory tentatively held out his hand until one finger touched the side of the penis. Once he had touched it, Gregory felt a gentle pat on his shoulder and Mr. May then took Gregory's hand in his own and guided it up and back along the underside of the cock. Once he had Gregory's hand well placed he let go of it and Gregory continued doing this: slowly and steadily moving it along the length of the organ as Mr. May had directed. While Gregory continued with this stroking Mr. May moved his own hand to the base of his phallus, including the balls so that the two of their hands together pretty much covered the whole thing.

The penis seemed to love the attention and became stiff to the touch and well elongated. No doubt it was a cock that Janet knew well and must have liked. The thought of Janet made Gregory wonder how she would like to hear of this crazy kind of homosexual encounter that was now going on. On second thought, she had been the one to buy the girdle and bra for him so maybe this was not a totally unexpected situation.

Gregory could tell that the discussion above him was winding down. It seemed that an agreement had been reached, all the parties were quite pleased and that Mr. May had arranged for a limousine to take the men to the airport. Gregory wondered if his stroking of Mr. May's penis was somehow an integral part of the success of the meeting. He heard one of the Japanese stand up and as he did so Mr. May somewhat roughly pushed Gregory's hand aside and wrestled with his penis to get it back in his pants. Considering how erect it was, that was no small task, but Mr. May was evidently quite adept at doing this. It helped that he kept his boner pointing up, pressed against his stomach, and then covered it with his buttoned suit jacket.

Mr. May stood up and took leave of the Japanese visitors. Gregory was relieved that this bizarre experience was finally over. For all Gregory knew, this kind of under-the-desk game might not be that unusual in the investment banking world, but if it was, he hadn't heard about it. Certainly, it was hard to imagine that very many men would help their boss masturbate, particularly while they were dressed as a woman. But all he had done was touch a penis a bit, how terrible a thing was that? Indeed, his own doctor had held his balls in the examining room. This wasn't the end of the world was it? Hopefully, Gregory and Mr. May would be able to resume their normal relationship after this episode so that Gregory need not have any fear of being fired or otherwise publicly embarrassed.

When Gregory heard the office door close he peeked out from behind the desk to confirm that the visitors were gone. He saw Mr. May coming toward him and as Gregory slid out from under the desk to stand Mr. May said, "don't bother. You can stay right where you are."

"What? Why?" Gregory asked.

"I'm not done obviously," Mr. May said and he sat back down in his chair. "Now I want a nice relaxing blow job. You've done a wonderful job thus far and I am very pleased. Thank you, Gregory. Now its time for you to give me a perfect blow job."

"Blow job? You mean put it in my mouth, Mr. May?"

"Yes, that's how it's generally done, haven't you heard?"

"Yes of course I have, but how can you ask me to do that?"

"Look, I'm still half erect and I like to think of it as your boner. You made it Gregory and I want you to enjoy it. Just a delicious boner for you to have fun with so let's get on with it. I've got some appointments later in the day."

Mr. May regarded Gregory, who was sitting on the floor in front of him, calmly and with a trace of affection. While Gregory watched, Mr. May unbuttoned his trousers, unzipped his fly and took out his penis. He had been telling the truth since it was still partially erect. "Now go ahead Gregory. I do so very much want a blow job."

"I'm sorry Mr. May but I'm having a problem with this. It just doesn't see right to me."

"I don't see what you mean. Between you and me, you're the one wearing a girdle and bra. Many women truly enjoy giving blow jobs. Once you start I'm sure you'll love doing it. You're well dressed for the role."

"I've never done anything like that. I've certainly never had one of those in my mouth."

"Well then, there is a first time for anything."

"If I do this, then what?"

"What do you mean by 'then what'?"

"What will happen to me here in the company?"

"Are you expecting a reward for giving me a blow job? A raise or promotion?" Mr. May laughed slightly and looked quizzically at Gregory.

"No, not at all. I think it might make you see me differently."

"I think seeing you in a girdle, bra and stockings qualifies for 'differently', but I assure you I won't hold that against you Gregory. Every man to himself - if you like wearing women's underwear then it's not really any of my or anyone else's business. But time is a wasting. I've got a busy schedule this afternoon and we can discuss this later, but right now I would like you to perform a blow job on me. You certainly know how it feels when a man is teased and not brought to fruition."

Gregory was at a loss as to what he could say now. He looked at the penis sticking up from Mr. May's crotch. There was pubic hair around it and hair on his belly. The top of the cock was a flaming red color. Mr. May spread his legs further apart. "Come on Gregory, this isn't so hard, no pun intended."

Gregory moved up closer and sighed in resignation. Mr. May was probably right. There would be an initial shock and then after that it might actually be kind of easy. What was involved anyway? Using one's mouth as a sort of vagina?

Gregory had never had a penis in his mouth before or even had a blow job done to himself. A couple of times he had seen women giving blow jobs in porno movies shown at friends houses, but even then it was hard to remember exactly what the women had been doing. Gregory arranged himself as comfortably as possible by placing his forearms on Mr. May's thighs and then skittishly moved his head forward toward the cock. Even before he touched it he could see the penis rise up in anticipation of his mouth. He closed his eyes and moved further up until he touched the very end of the penis with his lips. He recoiled at the sensation and then forced himself to lean forward again so that his lips were touching the top part. He felt the penis move a little. Then he slightly opened his mouth and admitted just the crowned end. As he did so the penis took another small jump that gave Gregory a start. He remained stationary with the end of the penis in his mouth. There was a slightly salty taste and he felt blood pulsating through the engorged red member.

Still keeping the tip of the penis between his lips Gregory raised his eyes upwards to see what Mr. May was doing. Mr. May had his eyes closed and a big smile on his face. Despite Gregory's inexperience it was clear that Mr. May was enjoying what he was doing. Gregory opened his mouth further and leaned forward slowly sliding the penis across his lips into his mouth until he had absorbed the entire organ up to its shaft. He was momentarily startled when his lips and nose came up against Mr. May's pubic hair and he opened his eyes. Mr. May's hair covered stomach and belly button was in view and Gregory quickly closed his eyes.

"Good, Gregory. I like what you're doing," Mr. May said as Gregory continued to hold the large stiff penis in his mouth without moving. The organ seemed to go through a succession of twinges in which it hardened imperceptively and relaxed.

"One thing you might think about," Mr. May said while gasping slightly, "man that feels good!, is doing the things that you, Jesus whoa!, like doing to your own penis." With his mouth full Gregory could hardly respond but if he could he would have said that he would try, though he wasn't sure that he could do the same things with his mouth only.

Gregory did know quite well which parts of his own penis liked to be touched and he figured that maybe he could touch the same areas on Mr. May with his tongue. He thus began to slide his tongue around on the underside of the penis and this was greeted quickly by more stiffening and a loud moan from Mr. May. "Bingo, Gregory!" Mr. May said. Gregory continued this awhile and then used a free hand to cup Mr. May's balls since he liked doing this to himself when he masturbated. It was also true that Gregory liked to rub his cock slowly when he first started to masturbate, finally increasing speed when it looked like he was getting close to the final release. The moisture supplied by his own mouth mixed with the precum leaking from Mr. May's excited penis was enough to insure that he could easily slide his mouth over the organ, and Gregory slowly pulled his head back exposing the wet phallus to the air. As he did so, he used his tongue to delicately stroke the sensitive parts of the underside.

Gregory gently rocked his body back and forth so his mouth slid naturally over the penis. His lips pressed down ever so firmly so as to maximize the amount of stimulation on the delicate organ. The fixed rigidity of the penis caused it to pulsate slightly in response to Gregory's caresses. "I can't believe you've never given anybody a blow job," Mr. May said as he gasped for breath.

Gregory looked up again at Mr. May and saw that his eyes were still closed but instead of the smile he witnessed earlier, Mr. May's face was contorted in a kind of strange grimace. It was the kind of face that he supposed that most people made not long before achieving orgasm. Though Mr. May's face looked like some one experiencing excruciating punishment, Mr. May was in a trance of pleasure caused by Gregory's careful ministrations over his manhood.

Gregory picked up the pace of his rhythmic in/out motion and Mr. May moaned louder and there was a slightly greater detectable throbbing in the penis. Gregory's hands felt some tensing of Mr. May's thigh and balls and figured that perhaps he was getting close to achieving orgasm. Just when he thought Mr. May was about to come Gregory heard a knock on the office door, followed immediately by its opening. From the way he was facing he couldn't see who it was and fearing who it might be - the secretary or one of his colleagues - he attempted to get the penis out of his mouth so he could hide again under the desk. Before he could move Mr. May grabbed him by the back of his head and said, "it's OK Gregory, nothing to fear. Keep up the good work."

Gregory struggled to turn around and see who it was but without being able to get the cock out of his mouth there wasn't much he could do. "Gregory, don't you mind, just continue."

Gregory sensed that the person was walking toward him and then he heard Janet's voice, "so how is it going Will?"

Mr. May said, "it couldn't be better. I'm already close to coming. He's really very good."

"This is such a scene! I wish I had a camera. Hi Gregory," Janet said leaning in closer so that Gregory could see her face.

Mr. May was helping pace the movement of Gregory's head as the cock slid in and out of his mouth. It was impossible for Gregory to make a coherent sound. Instead he managed to make a muffled acknowledgement of Janet's presence.

"Don't worry about it Gregory, I can see that you've got your mouth full," Janet said and laughed. "You look so darling in the pink underwear and I'm amazed at how well it fits!"

This led to more muffled sounds from Gregory. Janet continued, "you know, I felt so badly that I had obviously stopped you from buying the pretty girdle you wanted, that I spontaneously bought it for you right after you left. Then I got to thinking that you really needed a bra and stockings to go with it, so I bought them also. I hope you don't mind. I can't believe that I got the sizes right. The bra caused me no small amount of worry. Would your band width be 36 or 38, I couldn't make up my mind. Finally I decided to go with the 38 to be on the safe side and it seems like it fits you absolutely perfectly. You do look so cute in that outfit!"

Mr. May moaned softly and said, "you did really well dear. Even I have to admit he's got sort of a feminine cuteness about him in that underwear. If I didn't know better, from some angles I'd even see Gregory as a girl. He's certainly got the perfect instinct for blow jobs."

"Really honey? It sure looks like he's capable." Janet bent over to look closely at Gregory's sucking on the dick. "I'm so glad you're finally getting the blow job you've craved for so long."

"I still don't see why you won't ever give me one."

"I've told you many times Will, I just can't see putting one of those things in my mouth. They're not the most beautiful parts of the human anatomy. I don't know, I just think the whole idea is yucky. I have a mental block about it."

"Gregory isn't having any problem with it," Mr. May said.

"I can see that," Janet said. She kneeled down on the floor next to Gregory to get a better look. Gregory looked on helplessly making only muffled sounds as Mr. May continued to gently guide Gregory's head back and forth and Janet put her face just inches away from Gregory's. "Your cock has all these little veins and arteries and bumps and things and it seems so kind of slimy now."

"Gregory is keeping it wet so it slides real nice. I'm also leaking like crazy, aren't I Gregory?" Some more muffled sounds from Gregory followed.

"It doesn't appeal to me, though I am sort of getting turned on watching Gregory."

"It's as much fun for him as for me," Mr. May said.

"I think you're right," Janet said. She took one of her fingers and touched Gregory's lip at the juncture where the penis was sliding. "You're so big Will, it's a wonder that Gregory doesn't choke on it, and the way you make him take it all in, where does it fit in his throat?"

The conversation seemed to have distracted Mr. May since Gregory could feel a slight softening in the cock. Suddenly Janet laughed, "it's a wonder your pubies don't make poor Gregory sneeze! Every time he swallows you whole his nose is hitting them! That's one good reason why I can't see myself doing this."

Mr. May said, "Janet, I think you better sit back and let Gregory finish his job. I'm starting to tire a little. The wonderful thing is that you've allowed me this blow job - I've wanted one my whole life and finally I'm having it and its every bit as wonderful as I could have imagined. Of course, if you were giving it, it would be just that much better."

"How sweet, Will," Janet said, "I won't interfere any more. But why don't you at least let me help Gregory play with your balls while he sucks on you and I can also squeeze your nipples the way you like. This might help you get over the top."

"Great idea," Will gasped and Janet moved in closer and put one hand under Mr. May's balls and the other squeezing one of his nipples. At the same time, even without the encouragement of Mr. May, Gregory began to increase the speed with which he took the penis in and out of his mouth. He also pressed a bit firmer with his lips. The result was a clear build up in Mr. May's moaning and writhing in the chair. As he came closer to coming, he let go of Gregory's head and put one of his hands on Gregory's shoulder and the other on his wife's breast over her blouse.

"Come on Gregory suck that cock!" Janet said. "Your first blow job! Go Gregory go! He's so close now! Good girl Gregory, go girl go! You're such a hot babe! So pretty in that girdle and bra! Who knows what other nice little pretty things I might buy for you?"

Gregory didn't know what to make of Janet's cheerleading. Her remarks reminded him of the clothes he was wearing and the thought that she might buy him something more made his own penis ache with desire. He had no time to reflect futher on what she meant since he could taste that things were different with Mr. May. His penis was leaking heavily now and increasing in width, hardness and length as if it was about to shoot off.

All of a sudden Mr. May again grabbed Gregory's head and while holding it still gyrated his hips forcing his cock in and out of Gregory's mouth at a frantic pace with the result that he let loose with a huge spurt of hot semen into the back of Gregory's mouth followed by rapid pulses of additional white, viscous, male love juice. Janet screamed her delight, "oh my God I could feel your balls contracting, and there's come coming out all over Gregory's mouth!"

Mr. May let go of Gregory's head who in turn let the rapidly shrinking organ slip out of his mouth. Gregory collapsed prostrate on the floor and Janet stood up and looked down at him and what was clearly a bulge in his girdle. Gregory was too tired to try and hide it, and besides, he didn't really care what happened next. Whether the company kept him or fired him, or whether anyone else found out about what had transpired. It all seemed unimportant. What was important was that he had come face to face with his inner girl and it was something he would never give up or ignore again. If he never took off the lovely underwear that Janet had bought for him that was OK. If Mr. May called him in again to give him an afternoon blow job that would be OK too. Whatever. He knew that being a woman was now always going to be a part of his life.

Mr. May zipped up his pants, tucked his shirt in and otherwise got himself straightened up. He fetched Gregory's clothes from where he had stored them. "Here Gregory," Mr. May said, "you probably ought to get dressed. Janet and I can't thank you enough. You give a wonderful blow job Gregory. Thank you."

Gregory took the clothes and put his shirt and pants on over his girl's underwear. "If you don't mind Mr. and Mrs. May I think I want to wear these for the rest of the day."

"They're yours," Janet said sweetly. "You've done really well for yourself today."

"Thanks," Gregory said. A bit awkwardly he said, "I guess I'll be getting back to work now."

"Good bye," Mr. May said escorting him to the door while patting him lightly on the back.

As he waited for the elevator that would take him back to his cubicle, Gregory allowed himself the pleasure of feeling the delightful sensation of his new clothes. New clothes and my first blow job, he reflected to himself. Maybe Janet will have a change of heart about giving blow jobs now that she's seen him do it. She did say she might buy some other girls' clothes for him. Wouldn't it be great to have a dress or two? The elevator came and Gregory entered and pushed the button for his floor.

 

The end.

  

  

  

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