First Time Stories

[whitebrief]

Hi, looking hear about first time stories with underwear and m/m sex.
Myself, I had my first time after playing around and stepping out of my ck white briefs, the original full-cut ones as it was the 80s.

Hit me up at whitebriefs@gmail.com. Cheers

[nico711]

I wore red Papi trunks with the white waistband, that day. I knew what we were going to do so i wanted to wear something nice. The Papi trunks were made of the synthetic nylon mix that's breathable. It really displayed my bulge and butt really good. We had messed around in our speedos at the pool and other times I wore a black 2 xisit Y- thong or a jock strap.

[Tightthong]

A guy i dated about 2yrs ago got me a baskit nylon mesh jock when i first messed around...then he got me a JS bulge thong the night we first had sex...I've been hooked ever since.

[Cen0n]

i think the first time i was wearing white jockey bikini briefs and he was in ftl colored briefs.....

[iluvundies]

Mine I remember was a Calvin Klein Cotton Steel black thong, and he was wearing a white jockstrap, not sue what brand.

[MadAboutUW]

Not exactly sure what I wore, but I am sure it was a bikini brief of some kind... pretty much all I wore at that time. He, however.... wearing a pair of light blue low-rise briefs with the white piping around the waist and leg openings. We were both pretty nervous, but our mutual love of underwear helped break the ice in a hurry.

[WI Jockey Man]

My first time with another guy was a hookup setup on the Internet. I had a place to myself. He came by, we watched some porn, and eventually sucked each other off. I don't remember what I was wearing, but probably nothing special, this was before I started wearing better underwear than I do today.

I also remember my first pair of bikini briefs. I didn't have access to much having grown up in a rural area. One day when I was about 14/15 I found a pair on no brand bikinis that were red in a clearance bin at a discount store. I didn't have the balls to purchase them, so I shoplifted them. Didn't get caught (cause that would have sucked even worse). I blew a lot of loads in those bikinis I don't know if anybody ever found them where I had them hid at home...but nobody ever said anything.

[briefsUK]

Nice thread!
My first time with another guy, not exactly sex, just kissing and touching each other up, was with a guy my own age, about 16..... he asked me to guess what he was wearing. I wasn't sure what he meant at first , but he answered for me ..... purple briefs, and he asked if I wanted to see them ! Of course I did, and we went to my house where we were alone, he undid his trousers and I felt his purple cotton covered bulge, we kissed, and he undid my trousers to reveal my blue, red and purple patterned nylon slip from m+s. I was so glad I had those on !

The first time I actually had sex with a guy , I would be about 17 or 18, he was older, a really handsome guy in his 40s. I was wearing a royal blue m+s bikini slip. I had chosen it specially because I hoped we might have sex. It showed my bulge and bum nicely. He wore navy blue Hom bikini briefs, very narrow sides. We gave each other bjs. It was a really nice initiation. He was a lovely guy and we became good friends.

[MATT25]

The first time, he was older and experienced but I wasn’t so I was nervous. I was still wearing boxers full time and had on a pair of Hanes full cut light blue boxers with snaps. He was wearing regular white Jockey briefs. He had already stripped down to his Jockeys, which were stretched out by his hardon. He unbuttoned my shirt and pulled it off then pulled my white t-shirt over my head. Then then unbuttoned and unzipped my jeans and pulled them down. He said, “Oh, you’re a boxer boy” and unsnapped the snaps one by one. My shorts fell to the floor and my hardon sprung up. I pulled his Jockeys off and we went from there.

[boxerdude81]

First time I ever did anything with a guy (but not sex) was in college and the other guy was student and part-time campus security guard that was about 7 years older than I was. I met him on a dating site online and he happened to be local and decided to meet at a restaurant for dinner and we hit it off pretty good. Afterwards he invited me over to his house to watch movies (and maybe do other things). First we watched "The Rock," he sat on the couch I sat in his recliner. Half through the movie he asked if I minded that he took off his shorts, I told him "only if I get to take them off" So he came over to the recliner and I unzipped him and let his shorts fall to the floor. He had on a pair of teal FotL boxer briefs that were a little stretched out. He said, "let me put on nicer pair since you like underwear." He went to his bedroom and switched to a pair of black low-rise trunks that were a poly-microfiber material. He sat back down on the couch in his tshirt, trunks, and socks and invited me over to sit next to him. I asked him if he wanted to help get me comfy like he was so he came over, pulled my polo shirt over my head and then pulled off my cargo pants, leaving me in just my socks, black tshirt, and black under armour boxer briefs. I sat back down next to him and eventually cuddled up against him with his arm around me while we kept watching the movie. Eventually he started rubbing my arms and chest and I responded by slowly tilting my head up and pressing my lips on his. It was my first m/m kiss. After the movie finished we decided to move to his bedroom, we stripped off out tshirts and made out for nearly and hour in just our boxer briefs/trunks. The furthest we got was just mouthing each others bulges through our underwear. But it was great time.

We met up again about a month later at his place just before I graduated. This time we watched "Casino Royale" and started on the couch cuddling together, but fully clothed. As the movie carried on, we silently and slowly started to undress each other. A button here, a belt unbuckled there, a shirt tossed on the floor and so on. By the end of the movie all he was wearing was a light blue pair of silk boxer shorts and I had on a pair of red and black checkered Old Navy boxer shorts. We decided put in another movie ("Pure Country") and cuddled and kissed until we got sleepy and I feel asleep on his chest until waking up in the early morning.

[MicroModal]

I also remember my first pair of bikini briefs. I didn't have access to much having grown up in a rural area. One day when I was about 14/15 I found a pair on no brand bikinis that were red in a clearance bin at a discount store. I didn't have the balls to purchase them, so I shoplifted them. Didn't get caught (cause that would have sucked even worse). I blew a lot of loads in those bikinis I don't know if anybody ever found them where I had them hid at home...but nobody ever said anything.

- I can totally relate to this.
MM

[bikinilover]

I was wearing a red Undergear cotton contour bikini for my first time. We had been drinking at a street dance in our small town all day/night. After we closed the bar, everyone went their separate ways and I got a wild hair to drop by his house on the way out of town. He said later he knew exactly why I was there when he answered the door. I was drunk and scared, so I made up some excuse about wanting to see his remodeling. His house was a disaster, but we had a beer and chatted for awhile before he asked why I had stopped. I stammered out something about being too drunk to drive and asked if I could sleep on his couch. He showed me to an extra bed and stood there as I dropped my jeans. He reached out and touched the waistband of the bikini and said, "these are nice". I told him red was my favorite color and thought he might like them since he'd been wearing a similar pair on a recent trip where he and I shared a motel room with a couple other guys. After that we started fooling around and by morning I had experienced a lot of the things I was curious about.