Taboo Sex

Achieving Success

Daydreaming isn't fulfilling for this bi-curious closet sissy.

Spankmasters
May 21, 2024
11 min read
sissyGetting It Goodmarriedbottombicuriouscrossdresser
Getting It Good
Getting It Good

Achieving Success

Once upon a time, centuries ago, Jake reflected on the past while cuddling up to his wife in bed after a blowjob. It had been his first time experiencing fellatio, and his wife, Alexa, had been quite assertive about not swallowing. Despite this, she allowed him to ejaculate in her mouth. Curiosity consumed Jake as he pondered how difficult it could be to accept someone else's sperm in his own mouth. His mind was quickly filled with vivid images, envisioning himself giving a man a blowjob and indulging in the pleasure.

As a heterosexual man, Jacob didn't like the idea of having a homosexual experience, so instead, he fantasized about being the man who received the pleasure of a blowjob. Imagining himself in his underwear, he began to daydream about being in an array of women's attire, kneeling before a man, with their mouth eager to please him. Aroused by these thoughts, Jake reached out to touch himself and climaxed, without alerting his wife. Exhausted, he licked the sperm from his fingers, lingering on the taste as he drifted off to sleep.

Over the years, Jake had experimented with others but to no avail, failing to bring them to their climax. The thrill of merely imagining something had dwindled. He started to question whether he'd ever possess the courage to have an intimate encounter with a stranger while sharing a home with someone who would be upset by his actions but seemed desperately craved intimacy. He treasured his marriage, but his wife's detached demeanor during sex had caused him to seek elsewhere for what he desired.

One of the many men Jake had encounters with was Neil. A man between his mid-forties and mid-fifties, living alone, was an exhilarating and trusted companion. On one occasion, Neil had even attempted penetration without a condom, discarding the sperm on Jake's behind. On another occasion, Jake swallowed Neil's sperm, with a little help from Neil. Further down the road, Jake rendered Neil orgasms by his hands while masturbating. Jacob yearned to provide Neil a fulfilling experience, a fulfilling experience he never wanted to forget.

As a disguise, Jake opted for the name Lindsey as a feminine alias. Despite Neil's preference for masculinity, he didn't mind Lindsey's feminine appearance as long as his needs were met. Using the alias, Lindsey sent out a message, asking Neil if he was available for a visit. Although Neil would expect a handjob, she desired to grant him a surprise. After bracing herself and showering, Lindsey dressed casually and prepared to make her way to Neil. Parts of her longed for Neil to ignore her message. Fear consumed Lindsey, but she couldn't help but gravitate towards her hidden desire and clicked "Reply", to find a single response: "Now." Amidst a cloud of confusion and fear, Lindsey prepared to silence her hesitation, grabbed her bag, and made her way to Neil's house, unaware of the fate that awaited her.

Neil responded with a grin and motioned for Lindsey to enter. Lindsey felt secure with Neil and the haze was starting to vanish. Lindsey smiled and stepped inside Neil's home prior to him locking the door behind her. Without saying a word, Neil started walking through his living room towards the hallway that led to his bedroom. Lindsey understood this was her signal to follow, but she had a surprise for Neil this time. Typically when Lindsey visited Neil, he would hurry to his bed and shed his garments rapidly. A part of Lindsey's imagination entailed stripping a man of his garments personally. She also desired to tease him with a bit of playful sucking through his boxers to cause him to become aroused before removing his underwear to uncover a joyful phallus. Lindsey wanted to try as many of the erotic encounters that were conjured up in her lustful mind over the years and she wanted to build Neil up to an orgasm she hoped he wouldn't soon forget.

Before Neil could remove his own underwear, Lindsey put her hands on his hands, which were at the elastic band of his underwear, ready to eliminate them. Wordlessly and maintaining eye contact, Lindsey raised Neil's hands above his head and tore his shirt off. Lindsey moved closer and put her arms around Neil, hugging him while gently kissing and chewing on his neck while caressing his chest with her hands, being careful not to reach too close to his genitalia just yet. Lindsey continued kissing and chewing down Neil's chest to one of his nipples, sucking it gently while flicking her tongue across it, then moving over to offer the other nipple some attention.

Lindsey could tell Neil was appreciating the attention and she was herself becoming hot by now. Withstanding the impulse to get on her knees and take Neil's rigid member in her mouth took tremendous effort, but Lindsey had plans to make this visit unique. Carrying on with her kissing down his abdomen until she was kneeling, Neil was still in his boxer briefs. Lindsey could see his rigorously erect phallus bulging through his underwear. Without employing her hands, she gently placed her mouth on the trunk of Neil's dick and started applying modest pressure as she sensuously stroked it with her lips, making sure to saturate his underwear with her warm saliva. Lindsey's wife has done this to her during blowjob foreplay in the past. When her lover would remove her tights and panties, Lindsey would receive his member in her mouth, making sure it was saturated with her warm saliva.

Lindsey pulled away from Neil's boxer briefs, looking up suggestively before rising to take a shower and change into her more feminine clothes. Lindsey stood up and turned away from Neil, unbuttoning her trousers and walking out of them before disrobing her shirt so Neil could view her bare butt as she walked to his shower. Lindsey initiated her shower and started rapidly cleansing herself, believing that Neil would wait in bed relishing the cooling sensation of her moist saliva on his erection, but as she soaped herself, Neil entered the bathroom to observe and was now holding his phone, recording Lindsey naked in the shower. This shocked Lindsey, but also it was arousing to her. Lindsey soaped herself as sexily as possible, rotating and posing to provide Neil a good exhibition. Lindsey had no intention of wasting this event. She turned to face Neil, then lowered herself to her knees outside the range of shower water, still lathered in bubbles. With a sultry voice, Lindsey whispered, "Piss on me, daddy."! Neil didn't hesitate and, still filming, strode over to Lindsey before discharging his half-erect cock. Neil began urinating on Lindsey's face, her mouth open to accept his heated flow of man pee.

After he completed, Lindsey gulped down his semen then lewdly licked her lips before inquiring if Neil would care to join her. Neil removed his boxer briefs and entered the shower behind Lindsey, pressing his phallus against her soapy butt cheeks while he ran his hands over her soapy form, making his way to massage Lindsey's stiff dick, rolling his pre-cum on its tip while he kissed her neck. Lindsey couldn't tolerate any more and didn't want to reach orgasm just yet. She turned to face Neil, hoping he would allow her to kiss him. They locked in a deep kiss while Neil's robust hands encircled both of her butt cheeks firmly, Lindsey's hand gently pulling on his phallus.

Neil detached himself from the kid and declared, "Suck my dick." Instruction issued, Lindsey promptly crouched down and bolstered her efforts by sliding her lips over Neil's erect member, bobbing her head up and down while she slid a finger into his tight opening. Neil groaned with pleasure, but Lindsey wasn't ready to let him climax just yet, so she drew her mouth away after teasing his nerve endings, then went lower to work his balls.

In the past, Neil had inquired if Lindsey would rim him, and although she hadn't been comfortable with it at the time, she now wanted to try this sensual act for her turn at pleasing Neil in a way she hoped would lead to him pleasing her. Lindsey's plans involved taking her reward for initiating such a mutual and fulfilling experience.

Lindsey pushed Neil down onto his stomach and, after indulging in a little foreplay, delved into his backside. In a chokehold, Lindsey seductively snatched Neil's cheek in her mouth, teasing him with slight strokes of her tongue, gradually moving toward his anus. Neil, never at a loss for words, reacted immediately by shifting his ass into Lindsey's face. Lindsey's tongue delved into Neil's anus, accompanied by the occasional suck, and played with his scrotum. Seeing Neil's pleasure, Lindsey tossed him a gentle reminder of the recollection from their first casual encounter, when he'd tried to penetrate her but didn't go all the way. Her memories were full with the emotional connection she'd felt. Neil had skippered her to ecstasy by pushing his feelings inside of her. In this night, she'd return the favor by satisfying him with her mouth, a magnificent gesture she was intent on experiencing.

Neil was anxious, so he backed out of the pleasurable mission, turned off the shower, fetched his phone from the faraway room, and disappeared from the scene, alerting Lindsey to take her time with her own appearance since he was occupied. As she dressed, Lindsey was bewildered by her actions and anticipation, but she could no longer ignore the sultry feelings that completely engulfed her as she thought of giving Neil her all. Dressed in her attire, Lindsey could witness Neil's glorious body, lying in paralyzing stillness. His dick stood proudly erect, also granting her a view of its pre-cum, an indicator of his longing for her. Lindsey's methodical execution was preferable to latex clothes Neil had enjoyed greatly, so he was sure to savor the naked body in front of him.

Her heart pounding like a drum, she began her strip tease in front of the bed. Standing in anticipation, she rotated, allowing Neil to drink in the view of her body as it began to present itself. Once turned around, she'd wiggle her hips, uncovering her thong-clad ass partially, then wiggle her skirt back up. Following these stripped attempts, Lindsey slid out of her skirt, leaving her with only her garter, thong, and gossamer top. She swayed from side to side, giving Neil a peek at her garter-clad legs. Lindsey was transported by her own erotic dancing.

She unfastened her garter belts, undid her thigh highs one by one, leaving her readied for Neil's approval. In her want for Neil, Lindsey's excitement was physically manifested in her throbbing body, her clammy panties dripping with pre-ejaculate. She wanted Neil to see how tantalized she was and stood tall before Neil. Descending her skinny legs and crossing them, Lindsey removed her panties in a full display of her erection.

Neil could feel the anticipation building in his body as his gifted partner, Lindsey, was now eager to reciprocate by stimulating him. Lindsey crossed her legs and grasped the gold button on his jeans to open him while their gaze met in lustful eyes, marking the start of their erotic adventure.

Lindsey had already received her "Bachelor's degree" from Neil. This evening would bestow upon her the "Doctoral degree," awarding her the ultimate male pleaser's certification. Neil, having encountered so many adventurous women, could sense her eagerness and alacrity, as he basked in the knowledge she was about to spoil him in a way Neil had already done so for her. Neil, who usually gravitated psychologically toward men, was now lost in her naked, aroused flesh. The room was overflowing with admiration, curiosity, and pleasure, as Lindsey revealed herself to Neil with both her mouth and her body. Slowly, her fingers trailed from his dick to his anus, readying herself and him for the fulfilling moments that would soon follow.

Neil's raspy moaning indicated that his pleasure was escalating, and Lindsey sensed that he was close to reaching orgasm. To prevent climax, she twirled around his manhood with her mouth, then lowered herself, burying her head in the space between his ass and his torso. She felt in truth like a man, as her tongue probed and the overpowering ecstasy washed over his anus. Mere centimeters away was the prized centerpiece—Neil's butt.

Lindsey couldn't hold back any longer - it was time to take off her girly clothes, leaving just her black lacy thong. She turned back to give Neil a good look at her backside, then peeled off her camisole, chucking it at Neil's crotch to add a touch of femininity to what was about to happen. After stripping down to her undies, Lindsey jumped onto the bed, facing Neil, showing off her nakedness. She let her balls dangle from her thong while she moved her hips sensuously. She gave Neil's shaft and balls a peppy lick, alternating between softly sucking the tip and licking his goods.

Lindsey could hear the sound of a bottle cap being opened, but she was too focused on what she was doing to figure out what Neil was up to just yet. Shaking her booty slightly, mostly out of habit, when all of a sudden she felt Neil's finger circling her bum with some lube. He slid it in, then out, probing, like he was trying to spread lube inside her, at the same time getting her ready for something larger. After a minute, Neil pulled his finger out, and the bottle of lube got another opening. Before long, Neil inserted three of his lube-soaked fingers, which slipped in and out of Lindsey with surprising ease. Lindsey was amazed that she felt no discomfort, as her muscles had relaxed, allowing Neil's fingers to glide in and out. Lindsey couldn't help but suck Neil's member as she did this, lost in the euphoria.

Lindsey still felt a sense of emptiness in her bum. This date was almost perfect, but she wouldn't let Neil cum before she got a chance to fill that space with his dick. Lindsey moved forward on all fours, aligning her bottom with Neil's crotch, and positioning herself for reverse cowgirl, grabbing his shaft to guide it to her well-lubed ass. Just like years ago when Neil had briefly penetrated her, Lindsey was surprised how easily he slid into her, bottoming out and coming to rest on his lap, facing away from him. Lindsey loved the sensation, moving back and forth, enjoying Neil's presence. The two remained motionless for a minute, enjoying the sensations of their compatible bodies. Lindsey leaned forward, riding Neil so he could see himself fucking, letting him enjoy the pleasure.

When Lindsey tried to go faster, she was worried about Neils slipping out and causing harm as she went back down. She asked if Neil would fuck her from behind. Lindsey also wanted to know how it felt for a man to be in control in bed. Neil agreed and Lindsey got into the doggy style position, with Neil behind her. In one swift move, Neil drove his meat straight to Lindsey's almost virgin bum, thrusting deep and hard into her. It felt like Neil was pounding her insides, but this is how a man likes it, so the slightly uncomfortable feeling turned into experience. It turned Lindsey on that Neil viewed her as a man and that she was able to fulfill a man's deepest pleasures.

It was time for Neil to finish and for Lindsey to get what she wanted. Lindsey maneuvered away from Neil, laying her head over the edge of the bed. Neil thrust himself into her mouth, pushing all the way down without even needing a warning. Neil maintained this position for a moment, allowing Lindsey to adjust, then began thrusting in and out of her throat. It didn't take long, and after a few deep thrusts, Neil pushed himself all the way down Lindsey's throat, his cock buried against her nose, roaring out a moan of ecstasy. Lindsey bent over to continue, chugging until she could feel Neil slackening. Then, Neil pulled out of her mouth, leaving traces of cum and saliva. As Neil's dick hid behind his shorts, Lindsey suckled it one last time, tasting every bit of his cum.

Neil collapsed onto the bed, spent. Lindsey straightened herself and put her clothes back on, then quietly left. As Neil dozed off, satisfied with his empty balls, Lindsey couldn't help but feel womanly and included in Neil's pleasures.

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