My next excursion to the Lido was even more interesting. Leo wanted my help getting a costume. He also insisted that we go with his sister Claire, and Eliza, even though the two of them were more than capable of shopping for costumes by themselves. I had promised Teresa, so off I went.
Leo has been a close friend since high school. We know just about everything there is to know about each other, with two glaring exceptions.
We have acted as each other’s wingman on a hundred occasions. My buddy Leo is outgoing, dresses well, and exudes confidence. He is utterly fearless, and will approach the best-looking woman in the place. Bar, club, party, any social situation whatsoever – it makes no difference. And he strikes out every single time.
You see, Leo is 5′ 5″, has the body of Pee Wee Herman, and a face that only a mother could love. Yet when he looks in the mirror, Leo sees something completely different. Believe me, I’ve tried to tell him. I have suggested that he adjust his sights, and try to hit on the second best-looking woman he sees. I’ve tried to set him up with a less glamorous girl, or find him someone ‘in his league’, so to speak. No dice. He rejected all of my suggestions – they weren’t good enough for him.
The odd thing is, Leo has had a crush on Eliza since we were in high school. Eliza is his sister’s best friend. And she’s about the farthest thing from the type of woman he usually pursues as you could possibly imagine.
Eliza is tiny. She might be 5′ 1”, as she claims, but I doubt it. She has straw-colored hair and cute freckles. In my opinion, Eliza is quite pretty when she smiles (which she does a lot). She may be small, with no ass or hips to speak of, but she proudly carries a sizeable chest. Her boobs are probably not that large, but on her diminutive frame, they look huge. I’ve always thought of a pigeon when I see her in profile.
She’s a wonderful girl, and a good friend. We all called her “Ee”. I just can’t understand how Leo could obsess over her for a decade without approaching her once, while he has no hesitation at all when it comes to supermodels. I’ve never told him to give up his illusions.
The other thing I’ve never told Leo is that I would love to fuck his sister.
Claire is not the brightest bulb in the package, if you get my drift. Sometimes, you open the fridge door, and the light doesn’t come on. She also has an annoying nasal laugh, that sounds a bit like the neighing of a horse. To top it all off, Claire has a sizeable gap between her front teeth.
But Claire has long, dark hair, and a cute face, even with the gap in her teeth. And she has a body that would make a bishop horny. High, pert breasts – I think they’re 34Bs – a slim waist, swelling hips, and an ass like an apricot. Round, tight, and juicy sweet. She dresses well, like her brother, and when she doesn’t overdo the make-up, Claire looks quite good.
She has given me signs, over the years, that she was interested. There was a party, one time, when we were dancing. I can’t forget the song: it was ‘Love is the Drug’, by Roxy Music. In my defence, it’s a damn sexy song. Watching Claire sway to the music was mesmerizing. When she turned around and began flexing that shapely little ass, I was lost.
We ended up on the couch, with her sitting on my lap. The lights were low, and we necked for a while, with a little groping. Then we heard Leo coming down the stairs, and leapt apart as if someone had thrown a bucket of ice-cold water on us.
I didn’t want to date Claire, and I don’t believe that she was interested in a relationship either. Neither of us wanted to deal with her protective brother. We were a bit wary around each other after that. But there was no denying that the sexual chemistry had been there.
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