Seven years since you’d last seen your sister’s husband, Evan, when you were an eighteen year-old starting your last year of high school. Seven years since you had watched the way he confidently led your sister across the dance floor at the wedding reception. Seven years since you had (somewhat) guiltily fantasized that he would be consummating a relationship with you, not Alyssa, and that you would be joining him on the honeymoon to St. Lucia.
As you worked your way through another set at Charlie’s--there he was. You had taken this gig with a set of shows in the Boston area with the somewhat silly notion that you might run into Evan somewhere along the route. In fact, when you first saw him, you thought your mind must have been playing tricks on you, seeing what you wanted to see rather than what was actually there. But no, there he was.
Seeing him took your mind back immediately. On the night of the wedding, after Evan and Alyssa had left the reception, you had bedded the best man — Evan’s younger brother, Clay, who had just finished his freshman year at Northeastern. But when you stripped off your bridesmaid’s dress that night and turned around to lasciviously tug off your thong, it wasn’t Clay you were stripping for, at least not in your mind. And when you yanked off his trousers, knelt between his legs, and made his eyes roll back into his head with your lips and tongue, it wasn’t Clay’s cock you were sucking. No, you knew your goodie-two-shoes sister wasn’t doing this for Evan, and you so longed to drive him wild yourself. In your mind, it was Evan’s cock, rigid and throbbing at your touch.
Likewise, when you then crawled onto the bed upon your knees, angling your ass back at Clay, you invited him to take you from behind so you could picture Evan in your head as his brother’s cock filled you. The way Clay fucked you, thrusting feverishly until you surprisingly peaked twice, he must have wanted you like you wanted Evan. Surprising because, although you had been with several men, it was the first time you had cum from vaginal penetration, much less more than once.
In fact, it was your experiences with other men, as well as rumors about your romp with Clay, that led to your being sent away to boarding school to finish that last year of high school. While your mother considered you promiscuous and wondered why you weren’t more like prim and proper Alyssa, you considered yourself empowered and in control of your own sexuality.
Over time, you had further developed your sexuality through more experiences in boarding school - if your mother wanted to address promiscuity, boarding school was the wrong place to send you - and then in college. As you unzipped Evan’s trousers to feel his cock outside Charlie’s Lounge, you almost blushed, remembering your favorite vibrator in college, the one you simply called “Evan.” You later decided it had been childish to name a vibrator after him, but you had. It reflected the one man who had lingered somehow in your fantasies for all these years.
When Evan had left Charlie’s after locking eyes with you while you’d performed onstage, you’d been disappointed. Surely he had recognized you? He obviously liked what he saw. Why would he leave? Guilt for wanting his sister-in-law?
So when you left the lounge, and Evan called out to you, your heart thumped with adrenaline. Despite that rush of adrenaline, you coolly teased him about the way he’d been looking at you. You didn’t tell him the way your body had reacted as you’d felt his eyes upon you. Instead, you coquettishly kissed his neck, teasing out his reaction, after he drew you close for an embrace.
When his mouth met yours, and your tongues lashed against one another, your legs nearly buckled, but luckily, his hand on your ass held you tight against him. As confident as you had become over the years, you surprised even yourself when you unfastened his pants and stroked him through his underwear right there on the sidewalk. If his phone hadn’t buzzed, you might have let him take you right then and there. And he might have done it.
Damned if it wasn’t a moment ruined by Alyssa. Evan looked concerned as he read the text. “It’s your sister,” he said, in a clipped tone. “Wants to know where I am, and when I’ll be home.”
And so you said to him, as you zipped up his trousers, ““So, Ev, you’ve got a decision to make: go home to your wife like the good boy you are or come play with me. Your move.”
“You know what I want,” Evan said, as his hand lingered on your ass, squeezing you against him still.
“Do I?” you asked.
“Yes,” he answered, surprising you with another deep kiss. “But what I want to do to you would take more time than I can get away with right now. How long are you in town?”
“One more night,” you answered.
“Meet me tomorrow morning?” he asked.
You had waited seven years. What was one more night? And whatever your differences with Alyssa over the years, you didn’t necessarily want to ruin the lives of her kids over insisting on tonight and the questions Evan’s late return home would bring.
“Where?”
“The Starbucks on Boylston,” Evan answered. “In Back Bay. My friend, Dan, has a brownstone around the corner from there.”
“What time?” you asked.
“9:00?” he answered.
“Will you make it worth my while?” you asked, squeezing him again through his trousers. Evan didn’t answer. He just pulled your mouth to his and kissed you deeply in a way that said “yes.” After a lingering squeeze of your ass, he walked away.
The next morning, you arrived at Starbucks just before 9:00 clad in all black, including a short skirt, and your red lipstick. You ordered a grande latte and found a table in the corner of the Starbucks, a quiet space amidst the bustle of rush hour foot traffic. Worker bees, needing a caffeine fix to jumpstart their days, and college students, needing the same caffeine to clear the buzz of their hangovers. Minutes later, Evan arrived in a dark grey business suit, with a light blue shirt and a gold tie. He caught your eye, and you smiled at him as he stepped into line and ordered a coffee of the day, black.
