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Underwear Type: Life Timeline

mthomson2020

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First my current age: 23

I wore briefs from my toddler years until 6th grade, where I changed to boxers because that's what everyone else was doing to avoid having to be in them changing in the locker room.

In 10th grade, I started my transition back to the tighter spectrum of underwear. I wore mostly boxerbriefs from 10-12th grade, with boxers around 2 or maybe 3 days a week.

When I started college, I was pretty much wearing boxerbriefs 6/7 or maybe all 7 days a week, with boxers maybe 1 day that week.

I bought some briefs again to wear around my junior year of college to see if I liked them, and low and behold I did. So from then to the present, I pretty much wear boxerbriefs 4-5 days a week with briefs 2-3 days a week. I'll wear boxers 1-2 a MONTH, but usually just to sleep in if I don't have any clean gym shorts.

What about you guys? Have you stuck with the same type your whole life or gone through some sort of cycle.
 

tnman

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my current age:40's I too wore tighties until I got to be 20 or so, simply becauce that was what was bought for me. In my twenties I bought some boxer breifs and after a while they just rode up and compressed my junk, I then bought a couple of pair of boxers and have been hooked since then, I love the feel of "Freeness" and my nuts are always hang'in for free balling! It just works for me, and I would never go back
 

art

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Briefs from when I can remember through high school. (That's what everybody else wore, and they seemed easy to get out of the way for short-lasting random sexual encounters.) Went off to college & started wearing boxers -- for something new & because that's what most guys I saw naked were wearing. In my 30's started in with Midways, which constrained my cock and balls better. Now I wear all styles off and on, depending on my mood and what's clean. (Generally, I like boxers (short leg boxers) if I'm going to be walking around or if it's hot. Briefs if I'm going to be sitting down...because I really have that boxer seam coming across my balls!) I've been wearing a jock since 7th grade for any sort of athletic activity, or the promise of same. Made the mistake of playing a vigorous game of volleyball in a pair of jeans and boxers...Never Again. If I'm swimming -- not a contest -- and I'm not skinny dipping, I'll wear a short boxer-like suit with no liner.
 

MickeyLee

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underwear my mom bought me until about 9.
demanded underroos, of the boy variety.
started wearing boxer briefs around 14.
18-20 the commando years.
returned to underoos, sporting husky boy sizes.
currently rocking boy shorts and square fronts.
occasional trips into girl land with my ruffle boy shorts and hello kitty panties.
 

tieguy15

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me i wore tighty whities for until about 9
then boxers for about two years,
and at 11 i discovered nylon bikinis and have been wearing them ever since!
i love the silky feeling my balls are cradled in and never had a date complain about finding them under my slacks, although, i did get my balls busted a lot in the lockers growing up.
 

MMT22

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Tighty whities until age 16 or so, then went to bikini briefs until my early twenties. Back to tighty whities until my mid thirties, then I tried boxers. I have mixed it up some since then. Have been wearing boxer briefs for the most part, for the last seven years or so.
 

jockmaestro

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Briefs from when I can remember through high school. (That's what everybody else wore, and they seemed easy to get out of the way for short-lasting random sexual encounters.) Went off to college & started wearing boxers -- for something new & because that's what most guys I saw naked were wearing. In my 30's started in with Midways, which constrained my cock and balls better. Now I wear all styles off and on, depending on my mood and what's clean. (Generally, I like boxers (short leg boxers) if I'm going to be walking around or if it's hot. Briefs if I'm going to be sitting down...because I really have that boxer seam coming across my balls!) I've been wearing a jock since 7th grade for any sort of athletic activity, or the promise of same. Made the mistake of playing a vigorous game of volleyball in a pair of jeans and boxers...Never Again. If I'm swimming -- not a contest -- and I'm not skinny dipping, I'll wear a short boxer-like suit with no liner.
You've been wearing a jock since SEVENTH grade??! isn't it kinda ripe by now?
 

jockmaestro

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Briefs all thru hs and college. Fortunately, that's what everyone wore, altho it was new to me to see guys in the northeast where I went to college to be wearing boxers. I think those were the prep school kids. In the80's boxers became the rage,but I never wore them, except to sleep in sometimes. White pouch briefs all the way.. since 1960. Nuthin beats em.
 

darkbond007

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Age 30

White Briefs until I was like 13
Then I switched to Boxers until I was 18
Once I started college I got into Boxer briefs and I was that way until about 24 and had my circumcision. Had to wear briefs for a stint but these were now colored briefs
Over the last 2 years I have bought more expensive underwear and now I just switch between what I feel like wearing. The majority of my underwear is briefs and then boxer briefs. I have about 20 boxers just to sleep in.
 
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White briefs from JCPenny with the blue and gold stripe around the waistband until 16.
Colored bikinis from mid-high school.
Boxers starting in mid college.
Boxer-briefs starting in mid 90s

Now:
Boxers in the summer, boxer briefs in the winter. well fitted briefs when I am thinner.
 

B_thickjohnny

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briefs of various styles - regular FOTL or JC Penney when I was a kid through HS, then bikini briefs in a variety of colors were the rage from HS to my early/mid 20s. Then back to regular briefs but a lower rise. I tried boxer-briefs and boxers but I don't like the boxer-brief style because they ride up and frankly I find them hot in the summer months. Boxers are great in the summer under shorts but freeballing is the same so why bother with another layer of fabric? So I freeball in the summer and low rise briefs like CK or 2xist for the rest of the year.
 

xmarksbreakdownx

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I wore briefs until I was 10, then I started wearing boxer briefs and boxers. About 2 or 3 years ago I bought a pack of briefs to see what they were like, and I had to take them back. Very uncomfortable, and no where near enough room. Now I wear mostly boxer briefs. I think I own 10 pairs of boxers.
 

2xistTrunks

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Wore briefs (underoos when I was younger, then colored hanes) up until age 12.
Boxers til around my sophomore year of college mostly because that's what most other guys were wearing.
Around then started experimenting with everything from boxer briefs to bikinis and everything in between.
From the later years in college til now I mostly wear pouch trunks but also mix in some briefs and jock straps as the mood strikes me.
 

mattsrod7

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till about 6th, 7th grade where we had to change in gym, i wore tighty whities. Then I switched to boxer briefs, i told my mom I wanted something that went down the leg more. I needed something to restrain my cock, cause I got hard ons all the time, whether a lecture in class, walking down the road, watching tv. Then I wore those pretty much till about 23-24, where I wasn't popping woodies all the time and I gave boxers a shot, though I got boners a lot wearing them, so i slowly transitioned into them and now I wear boxers alot, though I prefer the support of boxer briefs, so I just wear what ever I pick up next in the pile.
 

bippy

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Current age: 34

Wore briefs to age 12, then switched to boxers (and occasional commando).

Added boxer-briefs around age 20, but didn't like them. Continued going commando more often. Was commando almost full-time during my senior year in college (22).

Mostly commando (with some boxers) from age 24. Full-time commando from age 30.

Why do kids always start with briefs? I always hated them and don't know anyone my age who wore them past age 12 or so. If I were a parent, I'd seriously consider starting my kids out either commando or in boxers.
 

darkbond007

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You should put kids in supporting underwear because of their active lifestyle. It helps them from injuring themselves.
 

ulu-ule

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Age 50. I wore briefs until I went to a boarding high school. I then went commando because it meant less laundry to wash... but wore jockstraps for sports (the school took care of washing team uniforms...)

For many years, for both running and work, I wore Undergear's "Sock," their more durable "Tactics Sock It Too" was briefly available also. They don't sell socks any more, I bought a "Man Zone" one a couple years ago and could barely fit one nut in it.

I now am wearing Undergear's "Body Tech" bikinis at work--my job is very physical. When I am at home, I put my cock in my hand or my wife.
 

MickeyLee

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figs, white pepper and white truffles..

is my favorite smell in the world *snurfles self*mmmmm melectable.
 

rrewards

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I started out with boxers and then my grandparents bought me some JCP briefs when I was in the 5th or 6th grade and from then I tried Jockey bikini and then stretch mesh, and then on to thongs and jock straps. I wear mostly the bikini in various colors and enjoy my thongs and jockstrap on warm days. I've thought about trying some girls thongs. They have a nice variety. I've seen some photos with guys on this site wearing them and I can't help but get excited when I see the pictures.
 

bignbubbly

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Your timeline is spot on with mine lol. Except now I wear briefs like 5 times a week and boxer-briefs 2 times. And I only generally wear Calvin Klein briefs, I love the look and feel on me. And I recently bought these Evolove bikini briefs at target - 2 for $12 - super hot and comfortable, check them out!
 

0837s

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I've been in boxers or commando my whole life. Can't imagine wearing anything tight- my cock has gotten too used to having freedom. I will wear the occasional jock at the gym, if i'm working legs, otherwise I freeball.
 

jockmaestro

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I've been in boxers or commando my whole life. Can't imagine wearing anything tight- my cock has gotten too used to having freedom. I will wear the occasional jock at the gym, if i'm working legs, otherwise I freeball.

I find this topic endlessly fascinating. In direct contrast to you, I have always hated wearing boxers. I can't stand my low hangers flopping around and have always preferred briefs. The briefs I wear now (2xist mostly) have a much better pouch than the classic JCP type tighty-whities, which appear to have been designed to suppress one's bulge slightly.
 

ulu-ule

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I find this topic endlessly fascinating. In direct contrast to you, I have always hated wearing boxers. I can't stand my low hangers flopping around and have always preferred briefs. The briefs I wear now (2xist mostly) have a much better pouch than the classic JCP type tighty-whities, which appear to have been designed to suppress one's bulge slightly.

Some of this "pouch" underwear barely offers a slight bulge. I need a "house" for my package, and am glad Undergear's line-up has kept me from doing damage to neither my environment nor my balls.
 

mthomson2020

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I hated boxers the first week i tried them. i thought it just took some adjusting but they never worked for me.

spent too much time worrying what other people thought about something as retarded as underwear. but hey, thats what we do as we age: not care about what others think so much
 
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mplsingleguy

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Tighty whites when I was a kid and then into high school I started to get my hands on some low rise briefs... college I got a few boxers but mostly I was still wearing low rise briefs- trying to be sexy. Right at the end of the college experience Marky Mark hit big, so I was off to start wearing almost all white CK boxer briefs. Over the last few years my drawers have taken a balance: one drawer for briefs (CK, 2Xist, Cin2, etc) one drawer for Boxerbriefs and trunks, one drawer for boxer shorts (lots of pin stripes and broadcloth "business wear" and a few fun cartoon boxer styles...) and the final drawer has long johns, jockstraps compression shorts etc so I can wear whatever I want based upon mood and purpose.
 
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894956

Ran across this very old post.
Briefs exclusively until my mid 30's.
Did wear boxers for sleeping as the next to final stage of reducing my sleepwear before a became a full time nude sleeper.
Tried the boxers I no longer needed for sleeping and like them for underwear, especially under suit pants, so I bought some more but continued to wear briefs at times especially with casual clothes.
By this time I had begun freeballing under gym shorts at home.
I very gradually began freeballing more, but never at work.'
Once I retired at 62, I continued freeballing more and more.
Within 2 years, I had stopped wearing underwear and got rid of it,
 
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