**Monday**
Jack was again slowing becoming awake, and as was his expectation over the last week, he was again sporting a significant morning erection. For once though, he was alone and was therefore imagining an energetic sex scene with a partner who he couldn't quite make out. She was wearing a long glittery dress, was blonde and had a gorgeous figure. It looked like they were having sex in a dressing room, when a knock at the door shouted "10 minutes Holly". Jack then realised it was Holly Willoughby that he'd watched hosting the 'Dancing on Ice' show the night before, and they were fucking before the broadcast. He enjoyed the fantasy moment, and gave her a very satisfactory orgasm, though for some reason he already knew she was a screamer so he had earlier stuffed pair of her silk panties into her mouth. She removed the impromptu gag, gave him a sexy kiss, then threw him out with her phone number scribbled on a napkin thrust into his tuxedo jacket.
He made it to the shower still very aroused, so played the scenario over in his head while he masturbated, then dressed casually while he planned the day ahead. Firstly he was expecting a visit from Alex the tailor, and Jack decided he would add a tuxedo onto his wish list there, though he doubted that it would be ready in time for the flight later that week, he could put it to good use when he eventually returned. Next was a visit to his solicitor to finalise and sign the agreement to the trial in the US, though at this point it would be a formality. Final planned activity would be his final pre trip physical and discussion with his doctors.
He was sipping on a coffee when his doorbell rang. Expecting the tailor, Jack opened the door to see a bright faced woman in a three piece suit, with a slightly punk hair style. "Hi I'm Alex" she said. Slightly taken aback, his face betrayed him so she added "Carlotta NEVER tells anyone I'm a woman" she giggled, and Jack's trance was broken and he invited her in. She brought in a sizeable suitcase and they started to discuss what was wanted. He told her that he was expecting to travel on Friday of that week, and whilst that seemed to take her aback, she indicated that she would do her best to get anything they decided on to him by Thursday.
Jack indicated he'd lost some weight and wasn't sure of sizes, but Alex insisted that she needed to measure him to ensure what he got was just right. So he stood up while she took out a notebook and pen, and the started to measure him all over. Neck size, arm length, chest size, waist size...whilst she was very efficient it did take a little time to get done. She then asked him to try on a couple of jackets for size, she took yet more notes and measurements, and then dropped the bombshell "I'm going to have to ask you to take off your trousers". Jack's earnest hope at that moment was that he would not betray himself while being measured here, but removed his clothing so that he was standing only in a pair of boxer shorts and a smile. A smile flitted over her lips, as the size of the resting cock still didn't leave much to the imagination given how much he'd grown in that area. She quickly measured his legs and thighs, and with a light professional touch Jack avoided any unwelcome swelling.
"I might suggest some new underwear too, something with a little more...eh breathing room than the ones your currently wearing." Jack nodded his assent to this wondering what else had to be done before he could get dressed. Jack almost immediately could smell the sweet scent of arousal from his tailor, and he cast his eye over her. With her jacket removed,he could see that the waistcoat was hiding a large pair of breasts, while the shirt was unbuttoned and gave him a very pleasant view of her cleavage, while trousers clung tightly to her hips and bum, showing rather than hiding her curves. His cock responded appropriately, and very quickly an unavoidable bulge showed in his shorts.
"My, that looks rather uncomfortable Jack..." and without warning she whipped his shorts to his ankles, his cock rapidly rising to attention. She swiftly unbuttoned and shed the waistcoat and shirt, leaving a bra supporting a pair of heaving breasts just short of his throbbing cock. She reached out with her finger tip, smeared some pre-cum before popping into her mouth, loudly sucking.
"I'm on a tight schedule Jack, or else we could do this properly, but I'm told I do a pretty amazing titty wank and I don't want you going off and taking care of this without me here." Jack assured her he would find that most satisfactory, So producing bottle of baby oil, and slipping off her bra (he guessed she was several cup sizes larger than Debbie who was a self proclaimed EE), she started to smear her breasts and cleavage with the oil, paying particular attention to her swollen nipples...she then leaned into him and licked the top of his cock, and wrapping her soft breasts around him , started to slide then up and down, each visit to the top accompanied by an eager lick or suck. He moaned with unbridled pleasure, the soft flesh wrapping around him whilst the oil caused an extremely erotic sensation to the whole thing. Alex cooed as she tended to his cock, moaning while she played with her nipples was she pressed onto his throbbing member. The whole thing was an assault on his senses, and the only thing that prevented him coming in seconds was the fact of his ejaculation an hour previously. As it was within a couple of minutes he recognised he was close, to which she merely pointed at her impressive breasts and groaned "paint my body". So Jack started to pleasure himself, wanking full length hard and fast so he very quickly came to the brink, but paying attention to his instruction, sprayed the the first three spurts onto her generous bosom. She then grabbed his cock and popped him into her mouth, sucking and licking to get the remainder of his cum and to clean his cock.
She then produced a phone, and opening the camera she said "quick take a picture of how it looks for me right now, I want this for later, hot stuff". Jack took a couple of snaps with the phone flashing brightly, then handed it to the tailor while quickly fishing a hand towel out of the downstairs bathroom.
She had started to clean herself up by scooping the cum and swallowing it, but the towel and some baby wipes that were in her case soon got her body clean and dry, to allow her to get dressed in front of him. "I'll make sure that your trousers aren't too tight for you gorgeous" she smiled. He'd ordered some formal trousers and couple of pairs of chinos, along with jeans and his vanity purchases, smart jacket as well as the tuxedo. "I'll be back on Thursday afternoon to finish the fitting. Please make sure we have adequate time to do that...properly." She packed everything away and before Jack knew it she was gone. He updated his 'therapy diary' and quickly dressed, recognising that he was due at his solicitors in an hour.
Jack arrived at the offices about 10 minutes before the due time, and was greeted by Julia, who was the complete model of professionalism. He couldn't help but admire how great she was at her job, whilst on a personal level had enjoyed her company enormously on Sunday. Before he knew it she ushered him in to Natalie's office and closed the door so they were alone. Natalie seemed a little nervous at first, stumbling over her introduction to signing the document, so Jack interjected.
"Natalie you're my solicitor. You're a great solicitor and I have nothing but complete respect for you as a professional, and nothing will change that. Now show me where I sign, or are there any remaining questions?" There were none, and the document was signed and witnessed (by Julia of course) in a few moments. Natalie asked Julia to scan and email the document to the lawyers that were representing the pharmaceutical company, and they sat and made small talk about his trip. No more than 2 minutes had passed when Scarlett was back on the phone, thanking Natalie for her assistance in promptly executing the agreement.