Lately I’ve been thinking about my first adult relationship. I was a sophomore in college, taking econ and business classes because that was a condition of my parents paying tuition.
We met because he was a guest speaker, invited to a panel because he was friends with my professor. It was a round table with other guests, and he was there in his capacity as the senior managing director of a hedge fund in the city.
The professor encouraged everyone to submit questions to the panel. I asked a question about something I don’t remember. I think it was about arbitrage.
Later, he called me a silly girl, said it was obvious I didn’t know what I was talking about and that I was in over my head in the class. Which I was.
I wasn’t a virgin, but I hadn’t had much sex at that point, and I’d only ever slept with one other person, the guy who had been my first.
He made a reservation at a well-known bistro on the Upper West Side for our first date. We sat in a corner that gave the illusion of privacy; outside the window, the line of people who had put their names down on the waitlist stretched down the block. I was too nervous to order, so he did it for me, and when the waiter took the menus away, his hand cupped my knee, his thumb stroking my skin in little circles.
That was the way of it. The small but firm touches. I didn’t even dream of denying him, much less asking him to stop. I couldn’t. I was too attracted to him, in awe of him, and humbled by his apparent interest of me.
He walked me home. When he kissed me outside my front door, it was a bossy sort of kiss. It was a prelude of things to come.
A few nights later, he picked me up and drove me to his apartment. There was a doorman, and his apartment had two full bathrooms, what seemed the height of luxury to me, living in the city. He rented a movie for us, a new political thriller we both professed interest in, but before all the characters appeared onscreen, we were fooling around.
I was naked and straddling him. He was still fully clothed. His hands were squeezing the globes of my ass as I ground down over his rigid length.
“I want to fuck you in the ass,” he whispered.
I stopped moving. I told him I had never done that before.
“Will you let me be the first?” he asked.
Of course I couldn’t say no to him. Instead, I stammered out my apprehension.
He said reassuring things. He teased the seam of my pussy with his fingers, loved my breasts with his mouth. It all made me feel so good, and I so badly wanted to please him. So at some point, I gave him the words he wanted to hear.
“Yes…fuck me in the ass.”
It hurt. It took a long time to prepare me. He told me that he would put toys in me later, and that would help, but he wanted the first thing I ever took back there to be his cock.
He used a lot of lubricant. It was cold and slimy and it still hurt when he breached my anal ring with the head of his cock. I didn’t want him to think that it hurt. I tried not to show it, but he grasped my chin and made me look him in the eyes.
“Be honest with me, sweet girl,” he said. “Don’t hide yourself from me.”
He liked seeing it, I realized. He liked seeing how his penetration in my virgin asshole was painful. He liked that I was grimacing and whimpering as he pressed himself deep inside me, that I was trying so hard to be obedient even as my body resisted this foreign entry.
“You’re being so good,” he soothed me. “Such a good, sweet girl.”
He reached down and tweaked my slippery clit until the bud swelled from under its hood again. I’ll never forget it. I was in a stew of confusion. It felt so wrong, and dirty, and painful. But when his cock withdrew, it stirred all sorts of nerve endings that made me gasp.
He took his time masturbating me with his talented fingers as his cock was buried deep inside my ass. He rubbed my clit, but he didn’t put his fingers inside my pussy, just stroked the lips and dabbled in the moisture there. I was groaning all sorts of shameful, indelicate sounds. I was in a torrent of conflicting emotions and sensations.
He made me come with his fingers, and when I did, that’s when he started fucking me ass in earnest. My body clamped down even more on his cock from my orgasm; that’s why he had me climax. My virgin channel squeezed his throbbing rod, which felt enormous. He quickened his pace until he came with a juddering thrust, emptying his semen inside me.
That was the first time. After that, he always took me in the ass. He never once fucked me in my cunt. He liked to tease it and tell me how needy and wet my pussy was, but he only liked my other hole. That bottom hole belonged only to him.
In time he trained me to orgasm from anal fucking. He did use toys, as promised. He was obsessed with my ass, punished it often, and my bottom hole. He subjected me to enemas, and introduced me to increasingly bigger and more irritating solutions. While the liquid he had prepared special for me was fucking my insides, he fucked my mouth, which was also fitted open by a ring gag for just that purpose. He never permitted me to give him a proper blow job, where I could close my lips around his length and lick and suck. Always it was with my mouth forced open into a nice round O for him to fuck.
And he never let me expel the enema solution until I had begged him right and proper like a desperate, degenerate slut. His hands would roam all over my body, milking my nipples, fondling my breasts. Sometimes he’d stroke himself off as he watched my trembling body, my insides cramping something fierce. He always gets off when he sees my suffering. But god, he’s rewired my body because as miserable as I get from those enemas, somehow I always get aroused.
Sometimes he put toys inside my cunt, to make my bottom hole even more snug, a tighter fit for his erection. But he was largely disinterested in that hole and usually ignored it.
Although he never said it explicitly, I understood that this was a condition of being with him. Being with him meant having him take me in my ass. Being with him meant carrying around a small tube of lube on my person at all times, and making sure I applied it before meeting him. Being with him meant having a sore butt all the time, from spankings and paddlings and whippings.
He liked to ask me to tell him how it felt, having him do all those things to my bottom. He liked it when I asked him for it.
“I want you to keep going.”
“Punish my bottom, please.”
Our relationship ended shortly after he got engaged. As it turns out, he had a long-term girlfriend who was finishing grad school back home, who would fly out to see him and who he would see on his trips. She finished her masters program and was moving to the city to move in with him.
His fiancé did not like anal sex and wasn’t open to it at all. She was beautiful and sexy and wild about him. I know because after he told me he had proposed, after he told me about her, he tried to persuade me to continue our relationship. I was different, I was special, he said.
I still couldn’t say no to him. So I let him gag me and tie me up and push a string of his favorite anal beads inside my ass, and I let him put me inside this wicker chest he had. The weave was loose enough for me to look out. His fiancé was in town for a short visit before her big move, and I watched them make love.
I watched him give her oral and watched her return the favor. She licked his big dick and made all these contented humming noises as she took just the tip into her mouth. So different from the sputtering, choking noises I made when he fucked my throat. So much less saliva and spit when her mouth wasn’t made to drool excessively from a metal ring.
I watched and listened as she moaned and screamed as he thrust into her pussy. All those wet fucking sounds as he rocked against her. My empty cunt pulsed in pity as my ass squeezed the anal beads.
I don’t know what he imagined. If he seriously thought that he could keep me in his life as his anal slut, and marry the girl from back home and have regular vanilla sex with her.
I wish I could say that I ended it. But the truth is, after his fiancé moved to the city, to celebrate the end of their long distance, she offered him anal. A homecoming gift of sorts. Maybe in exchange for his proposal.
He ended things with me not long after that. My next relationship was…different in a different way. But that’s another story.
gracieabrams
2087
romaincrisis
origamiaround
izzy806
tangentwithtanner
jimmyeatworldofficial
germansingergirl
