I met Gary through some mutual friends a couple of months ago, about a week or two after I broke up with The Ex. I wasn’t really interested in meeting anybody yet, so I didn’t see Gary that way. I did notice, however, that he is very attractive for a blonde guy. Clothes hang well on him, and he is HILARIOUS. That night he had me laughing harder than I had laughed in months.
I didn’t think about him again until about a week and a half ago. One of our mutual friends, Kelsey, was hanging out at my apartment for a night of wine and pedicures. Gary called her, and she invited him to join us. He declined, which isn’t too surprising considering we were drinking wine and playing with nail polish.
I guess she gave him my number because I got a text from him the next day apologizing for not coming to wine night. We started texting back and forth for two days before I invited him to come over and bond over our mutual hatred of Kelsey’s boyfriend, Ted.
Whose Lingerie Is This, Anyway?
He came over on a Friday night. It began with what had been promised: Ted bashing. Gary then spotted my acoustic guitar in my bedroom, and he sat on my bed to play a song. Let me tell you, this guy has a great country voice. Like, panty dropping great. He made up a song on the spot, and I wish I could remember the lyrics, because they were ridiculous.
We were both a bit punchy at this point, and one of us jokingly mentioned a text message he had sent me earlier that night. The text conversation looked like this: 
I confessed that I didn’t own much in the way of lingerie, but Gary didn’t believe me. I decided to show him my last lingerie purchase from several years earlier: a Mrs. Clause baby doll, complete with white fur trim and white furry pom poms. Gary found this hilarious, and dared me to model it for him. I jokingly replied that I would model it for him only after he modeled it for me. He inspected the craftsmanship of my Kmart lingerie, and decided that with the elastic back and mesh material it would be forgiving enough to fit his larger frame. He kicked me out of my bedroom for his transformation.
Gary didn’t model this over his boxers like I expected. He stripped down to just skin before putting it on. I will never forget how he looked wearing my Santa lingerie while covering his manhood with both hands. I laughed so hard, my abs were screaming and tears were running down my face. Gary changed back into his clothes and then threw me onto the bed. He pointed at me and said, “stay there” in a very serious voice before disappearing into the bathroom. When he came back out he snuggled up next to me and we just stayed there, joking around.
Naughty Fun
Somehow, the topic of boobs came up, and I mentioned my discontent with my 32B cup size. Before I knew it Gary’s tongue was on my nipple, and I remember saying that I’ve never let a guy play with my boobs before kissing me first.
He smiled and said that if he kissed me I would want to sleep with him, so he wasn’t going to do that to me since he wasn’t planning on getting laid tonight. Then he moved on to my other nipple. I said something about not wanting to sleep with him after seeing him in my lingerie, and we both started laughing again.
Break Check!
But he was right. I did want to sleep with him. We did everything but have sex that night. We had a lot of fun with my bag of sex toys, and I blew his mind with my oral skills (his weren’t bad either). When I was ready for the grand finale however, he refused to participate. He said he wouldn’t sleep with me that night, and I still don’t understand why. He had hinted to some naughty fun in his text messages, and while we did have fun and it was quite naughty I expected sex that night, dammit! It is half the reason I invited him over in the first place. Ugh, what a tease!
Regardless, I had a ton of fun with Gary. I haven’t heard too much from him since, which is fine. He is a good time, but I don’t want anything but a good time with him for a couple of reasons:
- I learned that he hooked up with one of my best friends six months ago
- He has a girlfriend, but he insisted that they were on a break the night we fooled around. Whatever, that is his problem, not mine.
Daisy's Diary 