Many years ago in college a guy friend, four female friends and i were playing drinking games. The last game I lost a bet. The girls came up with that I had to wear a woman's bikini bottom with them the next day at Kirsti's house to tan in. I had only worn board shorts my whole life, but always wanted to wear Speedos. I complied thinking a bikini bottom will never fit my 7.5in soft penis and I'll be able to get out of this bet very soon.
They soon brought me a black bikini bottom and a dark blue one and told me to try them on. I went into the bathroom and tried the dark blue one on. I didn't know the material is very stretchy and I actually got him all in, with some tucking and pulling on material. I then tried on the black pair. More room, not as much tucking and pulling on material.
Susie came to the door and asked How is it going? I said it's going fine and the black pair fit better. Im about dressed and im coming out. Susie said What!? No you need to quickly model them for us! The girls were not going to let me out of this and a bet is a bet. So I removed all my clothing and I put on the black pair again. My female friends didn't know my size, but they soon were about to see. I opened the door and turned the corner. Their jaws dropped, you could have heard a pin drop. I asked them What do you think? They smiled big and said they look great! They didn't know about my size and they didn't mean to put me on the spot like this and I didn't have to go to Kirsti's tomorrow to lay out. I said I'll still go. So I modeled the dark blue pair and came out. They liked that pair too, but hoped my package wasn't hurting, being too tight. They told me to hang onto them for tomorrow and I got dressed.
I stayed for a bit longer and talked. They had lot of questions. I walked back to my dorm room and shaved/trimmed.
The next morning, they picked me up and we went to Kirsti's. The day was fun and I received lots of comments on the black pair I wore and other girls wish their bf's would wear a Speedo.
During dinner, still in our swimsuits, Susie leaned over and said "your" Speedo is a hit. Let's go shopping for your own pair tomorrow.
Susie, Jen and I had fun shopping for speedos. I tried on several brands, but the material was thick and the girls didn't like the way they looked on me. Then the girls brought over women's bikini bottoms for me to try. I said No way everyone will know. Jen said, Not if you cut out the cotton crotch and look at the ones we brought. They all have the same cut as a guys speedo, except for no front pouch. I compared heavily and noticed she was right. She did miss one thing. A bikini bottom is a lot less expensive than a apeedo. We found a brand that fit me best. I got three pairs: dark blue with full back and a red pair and an aqua pair with a European back.
That week I wore them when we went to the apartment pool. I got comfortable wearing them. Then they all decided we all need to go to the waterpark the following weekend. I went with four girls and two guys. I was the only one wearing a "speedo". I got lots of smiles and comments from other ladies. Several girls would go up to my female friends and ask them how can they get their bf to wear a speedo. Another fun day. I have worn bikini bottoms ever since.