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Terri fucks her supervisor while being watched

"My sister's best friend gets thoroughly fucked while I surreptitiously observe."

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My childhood friend Terri has always been something of a flirt. We grew up together despite me being almost eight yeras older. She was (and is) my sister's best friend; I was kinda' like the older "big brother" who looked out for the both of them. Before now, however, I never believed that Terri would become involved with a married man. She was married briefly after high school, but that lasted for only a couple of years. At twenty-seven, she's now an administrative assistant for a large law firm in Houston, Texas.

I don’t usually think of Terri in a sexual manner, but it is impossible not to notice what a beautiful young woman she has become. She's slim and about 5' 6", 120 pounds or so. Despite her otherwise slight build, she is blessed with unusually large breasts, especially for someone who is so slim. I know they’re real, because I’ve witnessed her whole life! I suppose the best way to describe her would be as the quintessential blonde, "head cheerleader" type. She was, in fact, a cheerleader at Pasadena High during her junior and senior years. She won a few bikini competitions and wet T-shirt contests in college. Her cute and rather innocent face, slim hips, and firm, compact ass complete the package.

Terri has never suffered from a lack of suitors. She's had a steady string of healthy relationships with some pleasant young gentlemen over the past few years. The so-called trouble began last year when she stopped mentioning anything about her latest boyfriend. Her mom asked her about it; Terri just laughed it off, saying that she was "between men". After a few months however, even my sister began to suspect that she might be involved in some sort of clandestine relationship. She begged me to look into it.

Despite some initial reluctance to pry into a friend’s personal life, I became intrigued with the challenge and began driving by Terri's house at different times of the day. A pattern emerged. Two or three days a week, her red Acura was parked in her driveway at lunchtime. I found this odd because we all assumed she went to the gym over the noon hour. As I continued observing, I noted that a black Mercedes SUV was often parked across the street or down the block at similar times. It was there almost every Tuesday.

I suspected that she was meeting someone at her home. Stephanie (my sister) has a house key, so the following Tuesday morning at 11:30 I parked a few blocks away, let myself in, and secreted myself in her bedroom closet. The closet was only a few feet from the left side of her bed, and the door had slats in it that allow air to circulate. Even with only window illumination in the bedroom and the closet in darkness, I had no difficulty observing everything in the room without being detected.

Terri arrived shortly after noon. I listened to her close the door, walk down the hallway, and enter the bathroom. I heard water running; it sounded like she was brushing her teeth. A few minutes later the doorbell rang; Terri went to the door and answered it. I couldn't discern what was being said, but the conversation was very brief and whoever she was speaking with had a considerably deeper voice. Suddenly, the lights in the bedroom switched on and in walked a man! I was now thoroughly committed; it was quite impossible for me to sneak away.

I recognized the gentleman who entered the room as one of the partners from the firm where Terri worked. He was handsome with an athletic build, probably in his mid-to-late forties. My heart was pounding as I watched, he began undressing. He sat on the bed and removed his shoes and socks. He stood, removed his shirt, and stepped out of his trousers and boxers. They were neatly folded and placed on a chair. The now completely naked man climbed onto Terri's bed, arranged a couple of pillows, and leaned back against them, facing the door. His erection was obvious, and actually rather impressive.

My childhood friend appeared at the door wearing a red robe. She smiled sweetly at the man and he smiled back. Upon entering the room, she untied the sash around her waist, opened her robe, and let it slip from her shoulders. It folded into a pile at her feet, and she stepped out of it. Terri was wearing nothing but a tiny white G-string thong. It was the first time I had ever seen her naked (or nearly so).

She was indescribably beautiful! Her breasts looked like two ripe melons suspended from her chest, each one topped with a big, pink nipple. Those nipples were stiff, upturned, and fully erect. The curve of her waist was as exquisite as anything I had ever seen on a swimsuit model or in the pages of a fashion magazine. Her legs, long and shapely, were a study in feminine perfection.

She crawled onto the bed, turned around, and reclined in the man's embrace with her back against his chest. He wrapped his arms around her. While tenderly kissing her neck, he began to caress her firm breasts. He kept pushing her tits together while peering over her shoulder into the cleavage. I watched as he continued to knead and fondle her titties while gently pinching one or both of her nipples. As he rolled them around between thumb and forefinger, each nipple became even larger and harder, like a big pencil eraser. I couldn't believe how far they stuck out! Even in porno movies, I had never seen nipples like those.

All this was definitely having an effect on Terri. She was flushed, and her breathing rate increased. She busied herself by rubbing the man's legs and thighs with her hands. Every now and then, she would reach behind her. I couldn't see exactly what she was doing, but whatever it was made him moan repeatedly. I assumed that she was stroking or squeezing his dick.

After a few more minutes, she leaned forward and the man moved out from behind her. She lay back on the pillows and he positioned himself by her side. His level of arousal was extremely obvious now: his cock was red, rock-hard and swollen with large distended veins standing out along the entire shaft. It was sticking straight up, and thoroughly-aroused Terri reached for it as he lay down beside her. His left hand moved to her right breast, and they kissed tenderly. The open-mouth kissing started out as gentle, but it quickly became more impassioned as they continued to fondle each other. Occasionally the man would break off and move his head down so he could suck her titties. He would lick one nipple until it was long and hard, and then move to the other one. Also, he seemed to like pushing her boobs together and licking her cleavage; Terri appeared to like it, too.

By this time, I was as excited as I had ever been. I'd never watched anyone else having sex, but there it was, happening right before my eyes. Any doubts about what Terri was doing had been thoroughly erased, so I decided to just relax and enjoy the show. My cock was straining inside my jeans; I dared not take it out lest I unload all over the closet door.

The man sat up and swung his left leg over her slim waist. He moved up slightly and straddled her chest. He presented his erect cock to her, positioning it directly in front of Terri's angelic face. Mentally placing myself in his shoes, I knew that he wanted her to suck it. That's not what she did, however. Instead, she wrapped her long, feminine fingers around his shaft and stroked him softly. Every few minutes she would lean forward ever so slightly, open her mouth, and lick her lips. Each time she did this, she would gaze up at the man and smile, but she would never complete the act. He was about to go crazy, and all three of us knew it. Of course, she was doing this on purpose.

She paused, looked at his engorged penis and said, "Ahh, a nice hard cock!" His dick was hard, really hard.

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When she decided he'd had enough teasing, Terri tenderly grabbed his member down by his balls and directed the tip toward her waiting mouth. She licked away a glistening drop of pre-cum before kissing the end of his rod with her soft, red lips. Parting those lips ever so slightly, she sucked his cockhead into her mouth. After a few short strokes, she took him as deeply as she could. Her lips bottomed out, leaving a lipstick ring around the base of his shaft. He let out a sigh that sounded like the air being released from a balloon. Man, I'll bet that felt good! Terri began sucking enthusiastically, and the man asked her to slow down a little. Abruptly, he pulled away. He was breathing rapidly, and (from my vantage point) seemed to be close to cumming in her mouth.

He took Terri's head in his hands and kissed her passionately. As he began kissing his way down her body, she parted her legs and his face was soon buried in her hairless cunt. The G-string was first pushed aside, and then removed entirely. Using his fingers, the man gently spread the delicate inner lips of Terri’s pussy. Her stiff little clitty was completely erect and sticking straight out. Her entire pussy was deep red; she was obviously very wet. He began by licking her inner lips, gradually working his way down toward her asshole. He flicked it softly with his tongue, and then lightly traced around her little rosebud. Terri gasped.

As he continued to lick her, Terri's level of excitement increased. At first, she had her hands on his head, running them through his hair. As she reached up to grab the windowsill behind her head with one hand, she began moving her hips up and down, fucking his face. She continued doing this faster and faster as he licked her slit. He was literally fucking her with his tongue!

She was flushed and moaning continuously, rolling her head from side to side. Then both her hands were grabbing the windowsill, and she was humping his face so vigorously that her ass came completely off the bed with each thrust! Suddenly she froze in place and held her breath. Only a tiny, high-pitched squeak escaped from her throat. Her breathing resumed seconds later in ragged gasps punctuated by screams of pleasure. She was wracked by wave after wave of orgasmic ecstasy. The man looked up and licked her juices from his lips.

Terri made him stop licking by saying, "I want you inside me… right now!" Upon command, the man raised his head from between her legs. Terri scooted up slightly on the bed and repositioned a single pillow behind her head. She smiled at the man and spread her legs; she was fully aroused and eager to be mounted.

The man supported his weight on his left arm. With his free hand, he positioned his throbbing meat at the opening to her dripping love box. He entered her so… very… s-l-o-w-l-y, and soon he was pistoning in and out with long, full-length strokes. The man kept telling her how beautiful she was and how good she felt. Terri was pushing back hard against every thrust. Their mutual cadence was the very definition of sexual perfection.

The man briefly adjusted his position and then really let go of his bolt. He was drilling her fast and hard with precise strokes. Terri responded; she had a way of moving her pussy front to back (and sometimes sideways) while stroking on his big cock. It was awesome! From my nearby vantage point, I could hear their naked bodies slapping together as well as the squishing sound his rigid jackshaft made as it worked her pussy juices into a white froth.

"I need to cum again," groaned Terri.

So, the man asked her how she wanted to do it.

Terri flipped over into a prone position with her legs wide apart. The man placed a pillow under her hips and entered her from behind. Terri fingered her clit as she was being boned. It didn’t take long; within about a minute she was urging him on, "Stick it all the way in... My tiny little pussy is wrapped around your big hard cock… Fuck me, Paul... Fuck me!"

Oh, so that was his name!

Paul bit his lip.

"Oh Paul, remember that Friday when you fucked me, bent over in the executive washroom? Fuck me that hard again... Paul, pump me baby... Make me cum... Fuck me and make me cum!”

Paul held her tightly with both arms and kept pounding, “Fuck that dick! Cum for me, sweetheart… Cum all over my cock.”

Terri moaned, "Ohhh, I'm getting close... Harder!"

"Getting really close now! Ohhh, ohhh, ahhh..."

Her entire upper body flushed; she held her breath while the waves of ecstasy grew. Her forearms tensed and she dug her glossy red nails into the bedspread. "This… little… pussy… needs… to… come!" When Terri finally let go, she was screaming so loudly that I honestly feared it might attract the attention of her next door neighbors.

After Terri recovered a bit, she turned onto her back. Paul straddled her abdomen, reached into the nightstand, and removed a tube of K-Y. As he was liberally coating his straining member with the clear gel, Terri pushed her breasts together and purred, "Why don't you slip it between my tits now?"

I thought to myself: “Hmmm, today is definitely not the first time they've ever done this.”

He slipped his stiff, throbbing boner into her cleavage and began thrusting. My view of him titty-fucking the blonde former cheerleader was altogether too much for me. I quietly unzipped my pants and took my painfully-erect dick into my hand. There was simply no way I could watch this without jacking off, and I had already leaked so much pre-cum that lubrication was certainly not an issue.

It didn't take long for either of us! Paul's breathing quickened along with his thrusting. He grabbed the windowsill to steady himself as he fucked her gorgeous boobs.

Terri urged him on: “You’re such a nasty boy, comin’ over here just to fuck me… My boss would love to be where you are right now, wouldn’t he? The way he gets hard and stares at my tits all day… You know he is just aching to shove his big, stiff cock between them! He told me he beats off thinkin' about that. He wants to fuck me... all your partners wanna fuck me! But only Paul gets to fuck my titties. Yeah! These belong to Paul; they’re Paul’s titties, aren’t they? Fuck them!”

Paul became visibly flushed. She continued: “Fuck those big, soft titties… Cum for me, baby… Go ahead and send me back to the office with your hot, sticky cum all over my tits!”

With one final deep breath, he unloaded. The first spurt was so forceful that it landed near Terri's left ear. Great gobs of warm semen were pumped into her spectacular cleavage, and a few drops dribbled onto her nipples. As they separated, Terri and Paul remained briefly connected by white strands of his thick, ropy cum. I continued stroking and silently but energetically shot my own huge wad into my other hand.

Paul kissed Terri again, picked up a towel from the nightstand, and lovingly cleaned his spunk off her chest. They lingered in each other's arms for a few minutes. The conversation was whispered, and I couldn't make out any of it. After both of them left the house, I waited a few minutes, washed up, and quickly but quietly departed via the back door.

I now know exactly what is going on, but I can't relate this to my sister, and certainly not to Terri's mom! Really, how could I? My only decision is whether I can resist the urge to take in another, "Tuesday afternoon show"!

Author’s note: substantially altered for privacy.

Published 
Written by Action1466
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