Boxers or Briefs?

First off, let me state that as far as I am concerned there is a reason that underwear manufactures make so many different kinds of underwear for men.  You have boxers, briefs, boxer-briefs, bikini briefs, thongs (yes I am sure there are some men who wear thongs) all in a variety of colors and fabrics.  When I was a kid everyone wore tighty whities except for old men and fat kids who wore boxers.  Funny how times have changed and it is great that today there is a lot of variety to choose from.  Whatever type of underwear you choose for yourself is absolutely fine and you should not be embarrassed or ashamed of whatever choice YOU make even if that choice is ridiculous.  If you need a laugh check out these 9 ridiculous underwear designs at the following website.

http://www.underwearexpert.com/2013/04/9-ridiculous-underwear-designs/

So this blog is not about boxers being better than briefs or that tighty whities are for losers.  This is about the choice of underwear that I get to wear being made for me.  As you know by now if you have been reading along, I had a preference for boxers.  Yes I will admit that that decision was influenced by the consensus opinion that briefs are not cool and boxers are cool.  I already felt a little "awkward" and "geeky" when I was a teenager and felt I needed all the help I could get.  Perhaps in some twist of irony you need to be really cool to get away with wearing tighty whities and I was never that cool.

I felt like I was "tricked" into making the switch to tighty whities by my then girlfriend.  As we continued to date and began fooling around more and more in what I now call our "pre-marital foreplay." My girlfriend made it clear there would be no "pre-marital sex" and I was glad that in her definition sex only included "intercourse."  I found this kind of play rather enjoyable as it was certainly better than me just jerking off alone.  So far our play had consisted of exploring each other's naked bodies, but we were never naked at the same time, as well as masturbating each other, but again, never at the same time.

One day she suggested that we should try to masturbate together.  I though this was an interesting twist.  She explained that she just wanted to make sure that we were careful to keep my "products" away from her vagina (she was not on birth control at the time).  In order to "maintain the separation of powers"  (yes that is the exact term she used and I found it both humorous and interesting) I should wear underpants to help contain my sperm.  I figured, OK, that sounds like it would work for me.  She then brought out a bag that contained a package of 7 Hanes white briefs.  She explained that I should put on the briefs as they would help contain my ejaculation better and that plain white briefs could be easily bleached and cleaned.  It was a logical proposition and she made it while I was facing the opportunity to mutually masturbate with her so I agreed.

So I undress and put on the brand new clean white briefs.  They felt strange on me after years of wearing boxers and while I felt I looked ridiculous in them I didn't care as it was just me and my soon to be naked girlfriend with me.  She undressed but kept her panties on so there was an "extra" layer of clothing.  We laid down next to each other and after some kissing, cuddling and caressing she eventually reached inside my briefs and I reached inside her panties.  We tried to time it so that we went at the same time, but she actually went before me and then I went about 30 seconds after that.  She carefully pulled her hand out of my underpants and I pulled mine out of hers.  She asked me to lay on my back and she would be right back.

She went into the bathroom and I heard the water running and she washed her hands.  She came with a wash cloth then slowly peeled my new undies off then proceeded to wipe me down with the washcloth.  I found that attention to be very enjoyable.  She patted my dry with a towel.  Then she grabbed one of the other pairs of briefs and was about to put them on me when I spoke up and asked her for my boxers instead.  She smiled and told me I should put these back on so we could be ready to do it again spontaneously.  I considered this for a moment then agreed.

So I quickly learned that if I was with her and wearing boxers there was no activity but if I was wearing briefs then we often fooled around either mutually of at least she jerked me off.  In fact there was one time when I had brought her to climax but when she went to return the favor she discovered I was wearing boxers so she just gave me a kiss and said, "maybe next time."  Well of course, like Pavel's dogs salivating at the sound of the bell I began to make sure I was always wearing briefs when I was with her.  Eventually she bought me more and slowly but surely I had been tricked into switching to briefs.   I now wear then almost exclusively in that it is really the exception to the rule (see The Doctor Will See You Now to see what I mean.)

Anyway, like I said, boxers or briefs?  The choice is yours or in my case the choice was hers.  Why she wants me to wear briefs beyond what she has told me; cheaper, easier to clean, etc.  I really don't know.

Now in my next post I will tell the story of how I was first "punished" by her.  Not a spanking but some other sort of punishment as this relationship develops.  Thanks for staying tuned.