Dirty Sex Memories

Dropping his jeans in a hurry, he hesitated in his youthful insecurity and opted to leave his underwear on. Trixie turned around and did the honors herself as she hooked the elastic of his white fruit of the looms and tugged them down. His half erect dong flopped out. She squatted down on her high heels to where his thick cock was inches from her face.

"Wow! You should be out fucking cute little girlfriends with this big thing," she advised before taking the head into her mouth and cupping his balls with her hands. Within seconds, it swelled into its proud thick 8 inches and she stopped sucking with a loud pop to observe, "You are shaking. Is this your first time, baby? Have you had pussy before?"

He stammered his response, "Uh...well not really."

Trixie formulated a plan in her mind based partly on her sympathy for him and partly because of his impressive cock size. Wiping her mouth with her thumb, she reached into her purse, pulled out a fresh condom and tore it open while offering, "I'll tell you what. I'm gonna let you get some pussy for the same price as a blowjob but don't tell anyone. A handsome boy your age should not be a virgin."

Trixie had already been fucked by three men that evening. All three were middle aged, unattractive men with small cocks which was common among a large percentage of her clientele. Tearing open the square wrapper, Trixie lined up the condom with his hole then unrolled the latex Trojan up the shaft until the ring rested in his pubic hair. Standing back up, she slid up her leopard print skirt to her waist, bent over and put her hands up against the building.

"C'mon baby...come get ya some," she coaxed while wiggling her prone flesh as seductively as she knew how.

Bobby awkwardly shuffled his feet inside the constraints of his pants around his ankles until he was standing directly behind her. Holding his dick, he fumbled around between her legs trying to find her pussy through the fat until she reached around and put it in for him. Holding her hips, Bobby pushed his big dick into her pussy until his pelvis was pressed up against her smooth, milky caramel ass.

Despite his inexperience, he felt that her pussy probably wasn't very tight but the warmth felt amazing to Bobby even through the rubber. Thrusting his hips, he wasn't sure he was performing very well but all he had seen of the act was in magazines so he kept going, not sure how he could improve. For her part, Trixie was rocking back and forth while leaning against the wall. Her huge boobs were swinging in her tight braless shirt almost slapping herself in the face and muffling her grunts. When she began to moan, that was validation enough for Bobby and he started to pound his cock in her even faster. Soon, his grunts began to match Trixie's. He could feel her thick hairy bush tickle his balls as they slammed into her clit which only aroused him more, thinking back to all the hairy bushes he had jerked off to in the magazines.

His excited young male mind struggled to comprehend how good it felt to be fucking for the first time. The fact he was in a disgusting back alley doing it with a prostitute only made it better. Unable to manage both his arousal and the slick sensation of his dick pounding her pussy, he lost control before he could even grunt a warning. Electricity rocked his body as he twitched while he came hard into the condom. He bowed his head, clenched his eyes shut and moaned as pleasure overtook his body. Once his cum had rifled from his body in several shots, he shuddered while almost laying on Trixie's back.

Typically, she rarely had an orgasm with a john. Much more commonly, she faked them in order to hurry up the process. Bobby's big dick and youthful exuberance had her on the verge of an actual climax and she really had wanted one. Disappointed, she reached behind herself, and gripped the base of his rubber covered cock so that when he withdrew, the condom would not slip off. He pulled out and she turned around to see the entire reservoir tip and about an inch of the condom, full of a heavy balled up cum. It was dangling off the end of his dick and the weight made it almost fall off without touching it. While he leaned back breathing heavily, she pulled it off and threw it to the ground where it made a sticky squishy landing.

Genuinely curious she asked, "How did that feel? You look like you enjoyed your first piece of pussy."

While attempting to catch his breath, he swallowed heavily then in a tone that showed his shyness and not his gratitude, he puffed underwhelmingly, "I really liked it."

Looking down, she noticed his cock was still pointing toward the night sky, still fully engorged. In that moment, she decided she would do something she had never done before while tricking. Years of fucking for money had desensitized her pussy and affected her ability to orgasm. In the past, she knew the feel of a bare dick pounding her pussy always drove her over the top. Trixie needed to cum and this influenced her to take a chance with no condom. Her lust was in control and she figured the risk was worth the reward. She looked at this disease-free virgin boy with a big dick up and down and was confident he was the perfect opportunity for her to get off.

Stopping him just as he was about to pull up his pants, she propositioned, "Do you want to go again? It won't cost you nothin."

Bobby was definitely onboard with that idea and stood waiting for her to take the lead. Trixie pulled over a flattened cardboard box and covered the filthy ground before laying down on her back. From that position she raised her high heel covered feet in the air and guided the boy, "I don't want you to wear a rubber this time. Get on me and put my legs back as far as they will go. Then I want you to pound that cock in me like you are mad at my pussy."

Excited and not having to be told twice, he kneeled between her spread legs, his swollen cock was bobbing with his movement and directing all his faculties by that point. He didn't care that the concrete was hard on his knees. He didn't care that he was about to fuck a whore bareback. He didn't care that the ground was filthy and little pebbles were imbedding in his knees. To the contrary, he couldn't remember ever being more aroused. Bobby waited as Trixie hooked her knees over his shoulders so he would be able to utilize his forward thrusting weight to push her thick legs back as far as she needed. Once the scrawny six foot boy had inserted his big dong into her slimy opening, he added his weight, pushing them back only slightly. He twitched at the feel of her warm wet walls around his bare erection.

She gasped, "There we go. Fuck me hard Sweetie. Make me cum before you do and remember don't cum in me."

Trixie was on the pill, but after seeing the amount of cum he left in the condom; she was curious how much he still had in the tank. Up on his toes like he was trying to perform 45 degree angle pushups; Bobby began fucking Trixie. It was awkward, at first, because he was foolishly concerned he might hurt her. After a few minutes, he realized that would be next to impossible as she outweighed him by over 100 pounds. Becoming more comfortable, he pounded his prick into her well used cunt, harder and harder. It may have been loose at that point, but it still felt amazing, and her thick hairy pubic hair was mashing into his pelvis with every thrust.

"Fuck, there you go Sweetie! Like that! Yeah fuck me harder. Drill me! Harder," Trixie ordered while moaning.

Bobby's ass was a blur as he rigorously pumped her pussy like he had a grudge. Thankful he had already shot one load, he knew he would not have lasted thirty seconds in her warm wet pussy without a condom. His entire weight was bearing down under her knees, and the sound of his body slapping hers echoed against the walls even with the sound of city cars in the background. Once Trixie climaxed in a dramatic display of wailing and cursing, he was already struggling and trying to hold back his own eruption.

His balls were pounding against her ass when Trixie shouted, "Almost fucking there! Harder Sweetie! Fuck me!"

Both her and her and sweating profusely and it was rolling off his face and just as he was about to tire out, she screamed, "Ohhhhhh Fuck! Yeahhhhhh! I'm cummin! Aughhhhhhhhh! Aughhhhhhhhh!"

Her entire body spasmed and she quivered underneath Bobby. It had been such a long time since she orgasmed, she felt like she couldn't stop now. Her voice laden with desperation, she commanded him, "Keep going! Make me cum again. Treat my pussy like you are pissed at it! I want you to slam your dick in it with all ya got!"

Funneling the combined drive of his youth and his lust, he managed to find enough strength to do what she asked. He pumped her so hard, her back was bowed like the rails of a rocking chair. Breathing hard, sweat was dripping off the end of his nose and the back of his thighs were burning with exertion. His balls were aching and desperate to release; he shook his head as though that would help him hold back.

Eventually, she screamed, "I'm cummin again! Eeeeeeeee! Ohhhhhhhh! Eeeeeeeee!"

Digging her long orange painted fingernails into his back, she erupted from the overwhelming pleasure racking her generous form. Locking her eyes on his as her pussy goo'ed all over his thrusting cock, she could see that he was going to blast as well. Despite the intensity of her lengthy orgasm, she still managed to instruct the boy, knowing her pussy cream would provide enough lube, "If you have to cum, pull out and stick it in my ass! I don't care if you need to do it now! Just stick it in my ass and cum as hard as you want!"

Wasting no time, Bobby pulled his slime covered cock out of her pussy and pressed it into her ringed sphincter. With a 'pop' the head entered her thick ass, just in time, as his throbbing dong began spurting. In his inexperience, he crammed his thick cock balls deep into her tight sphincter with no regard for her sensitive anus. He was lost in the sensation of that tight warm orifice which felt like it was a hand milking the cum out of him. A grunt growled out of him, "Unnnnnghhhh!"

He stopped his hard thrusting but gave tiny subtle jabs in an effort to prolong the inevitable. Once the ejaculating had stopped, he remained suspended up in the air with Trixie's legs holding up his spent, relaxed weight. They both had achieved their goal and when Bobby pulled his still chubbed cock out of her butt, he collapsed on the ground beside her, trying to recover.

She turned toward him, with a look of surprised awe on her face and smiled, "You did good, baby. You did real good."

After he dressed, Bobby walked home excited, almost jogging. He was no longer a virgin and the seedy, dirty sex in which he had just engaged was embedded in his brain, driving his lust as it would do for the rest of his life. While at home, he relived the experience over and over in his mind, jerking off feverishly for two more climaxes before falling asleep. His orgasms felt like an out of control freight train rolling him over, each one just as strong as the last.

Over the subsequent years, that memory had been useful hundreds of times to help him shoot. Regardless, present day Bob was nonplussed as he stroked his meat in the barn, it still wasn't quite enough to put him over the top. Digging deep in the vault, he had one more experience that ranked number one on his all-time dirty sex list, and he was going to break it out in his memory banks. It was like a savory snack saved for a special occasion.

The year was 1978. Bobby was still living with his dad in that rundown apartment but very close to moving out. He and a few buddies had a plan in place to share their own apartment in order to split the cost. At 21 years old, he was making better money than he ever had, but still not near enough to support himself fully. Occasionally, he would get a hooker for a blowjob. For a couple months he even had a girlfriend, but he was always looking for that first time with something new. He was chasing the dragon of his first primally raw sexual experiences.

It was the era before internet porn, DVDs and even VCRs. In order to watch a good adult movie he had his sights set on an adult theater near him. While it seemed like the perfect dirty scenario to fulfill his craving, Bobby was always too embarrassed to go in. Societal judgment on such establishments left Bobby with the ingrained pathos that only losers and perverts went into those theatres. Bored and horny, one night, Bobby was thumbing through the dirty magazines he had already seen for the tenth time. Frustrated, he tossed them on his bed. A young man his age had urges and needed sex to fulfil those urges so without overthinking his choices, he set out to seek it.

Dressed in his cut off jean shorts and tank top, Bobby made the stroll to the theatre appropriately named, The Happy Palace. Stepping into the dimly lit lobby, Bobby paid for a ticket to a movie titled, She Likes em Big. He already felt satisfied in his optimism that this was exactly what he needed to fulfill his lust.

Awkwardly, he glanced around not quite sure what to do or where to go. After some painfully strained observation, indicative of his inexperience, he made his way down the hall until he saw a series of double doors leading into the single screen theatre. The flickering light from the screen projected a strobe light effect on the scattered patrons, amounting to maybe 20 darkened figures seated, all spread out around the theatre. It was a familiar scene to other cinemas he had visited but what differentiated it were moans and grunts emanating from the speakers.

As he scanned for a seat and walked up the aisle, Bobby was already hard as a rock in his pants. The filthy atmosphere was exactly what he was unwittingly searching for to fulfill his taboo sexual appetite. Most corner seats were taken so he went to the back row and edged his way past a person in order to find a seat in the middle of the row. Settling in, his eyes focused on the screen. Thereupon, was a cute little blonde getting fucked by a black man with a large afro and an even bigger cock. She was yelping and squirming as she was being stretched out by that huge black dick.

Bobby's own big dick was so hard, he had to shift it a few times to keep it comfortable in his tight shorts. Feeling the wet precum spot in his underwear, he needed to jerk off very badly. He knew that it was illegal to expose himself in a public facility, but he also knew these theatres existed for a reason. A buddy had once told him that yes, even though you aren't supposed to jerk off in the theatres, everyone does it subtly and the theatre owners turn a blind eye because they know that is what makes them money. They only intervene if there is too much illicit underground sex which may draw the attention of the police and subsequently cause a raid.

Careful not to be caught staring, he furtively shifted his eyes from side to side to observe those around him. He could see an older man jerking his cock about ten seats from him. The masturbator was a chunky, balding man flailing away on his meat. Suddenly, a person sat down two seats from him on his right but Bobby was too intimidated to look over. Looking straight ahead, he observed somewhat numbly as the black man on the screen pulled out and gave the white girl a huge cum facial. While the movie was exciting, that wasn't the real source of eroticism for Bobby. It was the filth on the floor beneath his feet and the raw lust rife in the air as he sat there in an environment that he felt he didn't belong. The excitement for him came from being a tourist, a brief occupant in a disreputable place.

However, he was frustrated with someone sitting so close to him necessitating him to sit in discomfort watching the movie unable to act upon his desire. Ten minutes later, he could hear the person next to him shuffling around before recognizing that squishing, slapping sound that clearly indicated someone was jacking off. Bobby was so horny that he felt about ready to bust. Knowing all the fellow patrons were doing as they wished helped him relax his own inhibitions. Tugging at his shorts, he allowed his big dick to flop out against his stomach. He had purposely not worn underwear, aware on some level that this would be his inevitable course of action.

Wrapping his fist around his thick, precum smeared cock, Bobby stroked it slowly, trying to wait on the perfect scene to blow his load. It wasn't long before the mystery person beside him let out a long muffled extended moan before kicking the seat in front of them. Startled, upon hearing it, he immediately stopped stroking because the voice was high and sounded feminine.

His porn theatre etiquette was disrupted by the possible presence of a woman and made him snap his head to the side. To his dismay and arousal there was a long legged attractive black woman who looked about 30 years old, her knees were up while she rubbed her clit furiously through her orgasm. The anonymous lady was watching Bobby jerk unbeknownst to him and this had sent her into orgasm much quicker than the filthy movie could have accomplished. As soon as her climax had subsided, she smiled then whispered to Bobby, "Thank you." Her eyes never leaving his cock, she motioned with her finger to move over one seat next to her as she directed, "Come over here."

Without thinking, Bobby hopped up, his feet restricted by his bunched up shorts around his ankles. He shuffled over while his dick swayed back and forth until he slumped down in the seat right next to her. She whispered, "I came in here to masturbate to big dicks and you have a nice big one for me to see in real life. Go on... jerk it for me. Use your other hand so I can see it better. Mmmm."

The thought of her masturbating while watching him jerk off amplified his lust. Three of her slender fingers were disappearing in her wet hairy pussy as their desire fed off one another's. Bobby for his part, stroked his meat trying not to prematurely blast off as she enjoyed the show. When that feeling arose, he would slow down, squeeze the shaft tighter in order to constrict the flow to the head and stifle the urge.

The black woman was intermittently moaning between mumbles to keep her fantasy going, "Mmmm. Jerk on that big dick for me! You want me to ride it don't you? You want me to be your slut and ride it here in front of everyone. I know how you are. You don't think I can take something that thick do you? I haven't seen a white boy with a dick that big but I will bounce all over it until it's mine."

Placing one foot up over the seat in front of her, she put the other leg over the arm rest between them, allowing her sandal covered foot to rest on his elbow as she released once again, "Oooooooohhhhhhh! Yeahhhh! Yeahhhh!"

Unable to maintain his composure, Bobby's cock shot high into the air and over his head with his first spurt. The next several shots landed on his chest while his entire body quaked trying to hold down his grunts. One leg quivered uncontrollably. Feeding off each other, the black woman was overcome into a multiple orgasm. Almost sliding off the padded, folded down seat, she had twisted enough in her ecstasy to show Bobby her exposed finger filled twat.

Calming down, once their mutual explosive climaxes had subsided, she brought her feet down to the dirty, sticky floor, and reached across the seat to grip his big tool. The girth and the slimy cum on his lap was also something that aroused her greatly. Pumping his cock before it had a chance to soften, Bobby leaned back in his seat. His shirt already a mess, he put his hands behind his head and relaxed as he allowed her to jerk him off. With her elbow out, she stroked it up and down, savoring the feel of his thick dong in her hand.