I didn’t know what to say to Phillip. His right hand moved to the top of my dress. It zippered from top to bottom. He fingered the gold zipper.
“I’m just curious, Terri. How did you choose this dress for the occasion?” he asked.
I smiled. I was standing with my back to him, studying the lavish drapery of the large room. The dress was made of shiny black spandex – skintight and with a micro-miniskirt hem. I never had worn a dress this revealing. A pair of black silk pantyhose and pumps of the same color with a five-inch stiletto heel completed my outfit.
“I tried not to over-think it,” I replied.
Phillip laughed at my coyness. I had anticipated his question, of course. The Little Black Dress had arrived in the mail a week or so earlier. I had bought it the day after Phillip had invited me to attend the opera with him. I had considered several other black dresses, but this one spoke to me as they say. It said, “I’m not a subtle dress. Gentlemen are going to notice you. It’s going to send a clear message to Phillip.”
I’m 22 years old and not usually not attracted to older men. There was something special, however, about Phillip, who is 57. A mutual acquaintance introduced us at a cocktail party and I immediately felt an attraction to him. It wasn’t solely because of his handsome face, trim build and his warm sense of humor. There also was the potential lure of experience. Friends my age who had dated older gentlemen had confided in me that experience made a difference in the bedroom. There was a self-confidence and an attentiveness to their woman’s sexual needs that many younger men lacked, my friends told me.
Now, Phillip was being particularly attentive. I felt him lower the zipper an inch or two, kissing the back of my neck and working his way down to the skin he had exposed.
We were on the fifth floor of the Opera House. At Phillip’s suggestion, we had walked up a few flights of stairs during intermission. He said it featured a stunning view of the skyline and he was right. Opening the drapes slightly, Phillip revealed the lights of the office buildings nestled around the city center. Then, he stood behind me, his hands resting on my hips for a moment before his right hand moved to the top of my dress. He lowered the zipper farther and glimpsed the strap of my sheer black bra.
“Phillip, someone could come in,” I warned.
“No one is coming in, Terri. This floor hasn’t been used for years. Can’t you tell by the dust and the jumbled furniture?”
“I hadn’t noticed.”
I had worn my hair up, my long dark red tresses piled in a bun. I felt his lips brush against the diamond earring on my right ear and then he returned to my neck, planting long kisses. I felt the dampness in the gusset of my shiny pantyhose. I thought Phillip was playing. It was our second date, the first over coffee and croissants and ending with a sweet kiss from him. His invitation to attend the opera thrilled me because it meant we had a mutual interest.
“We need to get back,” I suggested.
I didn’t respond.
“May I make one change to your outfit?” he inquired and I nodded my approval.
He reached into his suit jacket and showed me a thin black leather collar with a small D-ring. It resembled a choker, with the exception of the silver studs. In the short time I had known Phillip, I had sensed he was a dominant. But I didn’t know it for a fact until he placed the collar around my neck.
“Do you like it, Terri?”
“I do, Sir,” I replied, the honorific spilling out of my mouth instinctively.
He lowered the zipper more, giving him access to the hooks of my strapless 38DD-size bra.
“Do I have your consent, Princess?”
I paused, unclear about his question.
“To take off your bra,” he added.
He made quick work of the hooks. He was able to pull the bra out without lowering the straps of the dress from my shoulders. He kissed the back of my neck again and then slowly moved down to where the bra strap had been.
“I love the creamy softness of your skin; it’s a treasure,” he said.
I still thought he was playing. I was convinced he would zip the dress back up and I’d return, bra-less, to the performance. Men were like that, I thought. He’d show me off, as if I needed to show off more; my nipples hard against the spandex material. He might even leave the bra in the room as proof of what he had done; perhaps discovered years later when the opera needed to renovate the room.
He was teasing me, intent on my arousal and it was working. I was confident that I was right about his plans.
Phillip gently turned me so that I faced him, kissing me lightly on the lips. In the spike heels, I was at his height. His kiss was confident and eager, but in no rush. His hands returned to my hips and then slowly moved upward. As we kissed, he began to caress my full breasts, his thumbs slowly kneading my already-hard nipples through the spandex. Below us, the sounds of the opera’s second act filtered up to where we stood.
“Phillip, we won’t be able to get back in.”
“Not to worry; I have tickets for us tomorrow night.”
I nodded and smiled. I was surprised when he turned me again. If he wanted to take off the dress, he easily could have reached around me. He apparently had another idea. He began to lower the zipper – very slowly.
“Does this excite you, Terri.”
“It does, Sir. Are you trying to seduce me?”
He laughed and slowed the pace even more.
“I can tell you’re wet, Terri.”
“Very much so, Sir.”
I shifted my weight slightly, worried I would lose my balance atop the stiletto heels. He kissed the back of my neck and returned to the trail he followed with his lips and tongue, this time to my lower back. My breasts ached with desire. His right index finger traced a line across my lower back and our eyes met as I turned my head. He knew I desired him, knew that I was losing control and knew that I wanted him to finish unzipping this dress and slip it off me.
“Sir, will you please undress me?.”
He told me to face forward and place my hands on the window. As I did so, I felt the zipper lower, stopping at the top of where the dress covered my ass. I felt his right hand caress the spandex and he playfully spanked my right cheek.
“Are you wearing panties, Terri?”
“You’re nude under your pantyhose?”
“I am, Sir.”
“You’re a naughty girl.”
He spanked my left cheek, then alternated between the two. A man never had spanked me and it was not unwelcomed. I had fantasized about it and Phillip had given me my first taste. He reached under the spandex and caressed the black silk covering my ass. He told me to put my hands behind my back. He used silver handcuffs to bind me. Instead of unzipping the rest of the dress, he lifted the hem to reveal my ass.
“Oh, Terri. I’m at a rare loss for words.”
He ripped the back of the pantyhose and I lost my breath from his sudden show of power. His fingers made contact with my pussy. I moved my legs further apart as he dipped his thumb into the wetness of my sex and toyed with the entrance to my back door. His right index finger began to circle around my clitoris.
“Is that good, baby?” he inquired.
“Fuck yes, Sir. I need more.”
“Just the beginning, sweetheart.”
From where I stood, I could see a sliver of his reflection in the glass. He shrugged off his suit jacket, loosened his tie and undid his belt to lower his pants. He took off his shoes and socks. He was wearing navy blue boxer briefs and I couldn’t keep my eyes off his large bulge. I don’t think he knew I could see him. His reflection vanished as he lowered himself to the floor.
I sighed as I felt his lips kissing around my pussy, teasing me again. I didn’t expect him to move to my anus, but I felt his tongue slide inside and I moaned, moving my hips as he delved deeper. I felt my legs tremble slightly as I discovered this new sensation. His tongue paused several times, his hands gripping my thighs. He was methodically building my need. I wanted to touch my heavy breasts or reach back to touch his head, but the handcuffs prevented that. My moan turned to a whimper. Phillip took that moment to withdraw his tongue. I turned and noticed he had a tube of KY jelly and began to lubricate my back channel, his intentions now crystal clear.
When I was ready, Phillip stood. He lowered his boxer briefs and placed his hands on my hips, telling me to bend my back slightly. He entered me with his cockhead and I felt my anus clench against his steel-hard cock.
“First time for anal, baby?”
“I thought so. I’ll go slow.”
I felt the tip of his cock throb and I moaned as he slid his shaft inside an inch or so deeper into my ass. In the reflection of the glass, I could see his face, his expression determined and his muscular chest heaving as he slowly guided his raging erection.
“Fuck, you’re so tight, Terri. Are you OK, honey?”
“Are you ready to take me?”
“I am, Sir.”
He drove his cock into me and I cried out, feeling a momentary tinge of pain as he filled more of me. I leaned forward slightly and moved my hips. The sounds from Phillip’s mouth were guttural. “Give yourself to me,” he said. I backed up, taking more of his shaft. He had lubricated me well and the pain subsided as he began to pump, preparing to push into me from the root of his penis. He spanked my ass again, this time harder and I felt a sting. I didn’t know how far he would push me, but I wanted more of him.
“Fuck me harder, Sir,” I begged. He responded immediately, a slight smile on his elegant face as he buried his cock inside me. He began to pound me, his rhythm consistent as he claimed my ass. I screamed as I came, the ecstasy overwhelming me as he plunged his cock into me over and over.
Phillip removed the handcuffs and turned me, kissing me lightly as he released the hair tie that held my bun. My long dark red hair cascaded down my back.
“Suck me now,” he implored.
As I knelt in front of him, Phillip lowered the straps of the dress to reveal my breasts. He kneaded my nipples, then moved his right hand to cup my chin. He placed the tip of his finger in the D-ring of my collar.
“So beautiful you are, Terri,” he said, as I looked up into his eyes.
He was still hard, his dick slit glistening with pre-cum. I licked it dry, savoring the sweet taste.
“I want to own you,” he added.
I took his cock inside my mouth and began to suck him, my right hand grasping his thick shaft as I swirled my tongue around his cockhead. I was aroused by his words of dominance. His breathing quickened and his head reclined as I bobbed my head faster, enjoying this fellatio more than any of the previous ones with other guys. The music swelled from below us and the only other sound was my cock-sucking and his praise for it.
“Princess, that’s so good. Please don’t stop.”
I took him deeper, then withdrew to lick the underside of his shaft as I cupped his balls, heavy with semen. His staying power amazed me. Other lovers would have come by this time, but Phillip’s erection grew. He reached down and stroked my hair. I kissed his cock in reverence and inhaled his musky scent, which drove me wild. After rolling my tongue over his cockhead again, I resumed sucking him and he came with an exuberant shout, his hot cum flowing down my throat in a stream that I barely could handle. I swallowed the first burst, but he pulled out and shot the second, third and fourth ropes on the front of my dress below my breasts.
Phillip helped me get up. We kissed and he embraced me tightly. We were in no rush to go anywhere. He found my bra, helped me put it on, lifted the straps of my dress back into place and lowered the hem. I gathered his clothes to help him get dressed. Before leaving the room, Phillip used his silk handkerchief to wipe the cum off my dress. “Very thoughtful,” I said with a smile and he laughed.
Half an hour before the opera ended, we walked downstairs to the lobby. An usher, an older woman, told me with a smile at the door: “That’s a stunning little black dress. You’re glowing and lucky to have an older, handsome gentleman like that. You look like you enjoyed your evening, whatever you did, young lady.”
I kissed Phillip and told her good-night.