So here I was, living in a small country town. I'd moved in with my Aunt Lydia when my parents divorced a few years back. I was 22 years of age, doing odd jobs around the town. I was content with earning some cash and getting some work experience as well. My Aunt Lydia who was a divorcee worked as a secretary at the local council. We got along just fine, so much that I would say, we had become good friends. I contribute to the running of the house, although Aunt usually does the washing and cooking.
"What on earth are these?" Aunt Lydia said as she stormed through the room holding a pair of my underpants.
"What do you mean?" I asked
"Jason, all your underpants I've washed are either torn or worn. You really need to get a new pair." Aunty said.
"Yeah I know. It's just that I've been busy and haven't had the chance lately" I replied.
"Look, I'll ring Janet, an old friend of mine who makes great clothing designs of all kinds, and she'll fix you some in no time. Save you some money that way" Aunty said.
A week passed, and Aunty Lydia had contacted Janet and gave her my waist measurements. It was only a matter of time before we received a parcel with underwear on our doorstep.
"Here they are, I knew she'd whip them up in no time. She's a clever lady. Try them on and see how they fit" Aunty said holding my new underwear.
"Ok Lydia, I'll try them on in a second" I replied. I watched Aunty as she walked by and noticed her massive breasts. She was a curvy women on top, with a curvy frame. She had just come home from work, and was wearing her grey skirt that finished to her knees, and white buttoned shirt. Her breasts were more then a handful and she allowed about an inch of cleavage by unbuttoning the first few buttons of her top.
As Aunty left the room, I tried on my new jocks. As I tucked my cock into the underwear I felt there was a lack or room at the front. The jocks tended to fit well around the waist, although it was incredibly tight at the front. I wasn't erect or anything, it's just that I was used to my old underwear, which I had grown into. My cock was one of those cocks that would stay four-five inches long when it wasn't erect.
"So I guess you're a big boy" Aunty said from the entrance of my room.
"They're a bit tight at the front" I replied. Aunty walked over to me, and felt the material, casually gliding her hands over my cock.
"Yeah, I think you'll need to see Janet personally, she'll have to custom make you some." Aunty replied. "In the meantime, you can use your old jocks. Or if you like, you can wear nothing, I certainly wouldn't object" Aunty joked as she left the room. I was left with a growing boner.
A week passed and I arranged to meet Janet. I knocked on the door, and we did our introductions. Janet was about in her mid-forties and quite bubbly. She had big curly red hair, and a great set of tits. She was a little more rounder then Aunty Lydia, and maybe her tits were slightly bigger. Both would have easily have been double D's. Janet was wearing tight jeans that really defined her backside, and a tight black T-shirt. What a great pair of tits she had I thought. She had a generous amount of cleavage on display as her top finished rather low. The more she'd bend down, the more view you'd get.
After small talk, we got down to business.
"Now Jason, I'm going have to ask you to remove your clothes so I can get your measurements right" Janet said.
I was kind of nervous, yet excited to get my gear off in front of her. I pulled my shirt off and my slid shorts down. I slid my old jocks off, and Janet picked them up. I stood there naked in front of Janet as she sat on the couch preparing her tape measure.
"Wow, your Aunty did say you were quite a handful, but I didn't know she meant it in that way" Jane commented with a glowing smile on her face. Her eyes focused on my loose 5-inch cock. "I've worked with many men before, and I have to say it's always a pleasure, especially someone like yourself. You've got a lovely penis. I just thought I'd say that, and get it out of the system" Janet said.
"Come here" Janet said. "It's obvious the jocks I sent you were too small around the groin area. I just need to take a measure of your cock, so could you just stand still for a moment". I stood there, as she sat on the couch eye level to my cock. She put her reading glasses on, and began measuring the length of my cock. She seemed very professional and focused. She used the term "cock" in such a way that it seemed like she used the word in every day speech.
Janet put the tape measure against the length of my cock, and noted the length. "Okey, that's 5 inches" she said. Then she'd rap the tape measure around my cock, and then around my testicles, taking note of the size. She looked very professional. As I looked down, I could see a beautiful view of her breasts. She'd press her tits against her knees, and her tits would push out of her top. They were so full.
My cock began to stiffen slightly. Janet noticed that. "It's ok honey, let me just measure it again. Well, so now you're 6 inches", and she scribbled out the previous measurement and wrote the new number. "Now you're not going to keep on growing on me are you" she joked.
"I'll just need to measure your waist again, and see if the measure meant you gave me was correct. Janet stood up, and leaning forward she put the measuring tap around my waist so the end measurement would meet at my rear. She bent forward and around her head went to confirm the number. Meanwhile, my cock pressed against her top, and I could feel the coolness of her cleavage press against it. As she pulled away, my cock had become fully erect.
Janet looked down and smiled at my cock. "What have we here" Janet said. "That's perfectly fine Jason, nothing to be ashamed of. I actually need it in full growth to determine the room the underwear will need to be to accommodate your big cock. Oh gosh you're gorgeous" Janet said as she bent down kissing the head of my cock. "I wish I could have you all to myself." Janet added in a maturely friendly kind of way. I wasn't sure if she was hinting at something or just passing on a complement.
Janet measured my cock again. "Now, that's 8 inches, you're not going to get any larger I hope. Well actually, I wouldn't complain" Janet joked.