Getting It Good

It all started many years before, one night after a blowjob, while lying in bed, Jake began to consider how his wife could let him cum in her mouth but was firm in her decision to not swallow. Jake was the first man Alexa had ever been with sexually and the first man to ejaculate in her mouth. That was when she decided she "didn't like the texture sliding down her throat". From that time on she would hold the cum in her mouth until she got to the bathroom to spit it out. Jake wondered to himself how hard it could really be? This naturally stirred up an image in his mind of himself letting a man cum in his mouth. Jake started to realize he was starting to get real turned on by this thought and decided to go with it to see where it went.

Jake slipped his hand down his pajamas and began to masturbate while fantasizing about satisfying a man with a blowjob. Because Jake was straight and turned off by gay sex and because in his fantasy he was the dick sucker he began to imagine himself as a woman dressed in a way that would be visually appealing to a man while getting sucked. Jake began to imagine himself in sexy lingerie on his knees with a man.

Jake climaxed harder than he had in a long time. Not wanting to wake his wife to wash his hands, Jake lustfully ate the cum from his hands and fell asleep with the taste of cum on his pallet. That night while his wife was asleep next to him, Jake found that he was extremely turned on by the thought of pleasing a man sexually.

Over the years Jake had met up with a few men and had mostly unsatisfactory experiences. Jake had yet to bring a man to orgasm. Fantasizing had lost its spark. Jake was starting to wonder if he would ever get over his fear of having casual sex with strangers while married to a woman who wouldn't understand but who also seemed to lack intimacy during sex. Jake longed for intimacy but had come to accept that it would never come from his wife but he loved her and she needed him.

One of the men that Jake had a couple brief encounters with was a man named Neil. He was in his mid fifties and lived alone. Neil was the man who a couple years earlier had been the first, and still only man, to briefly penetrate Jake bareback but didn't want to cum in him so he pulled out and sprayed all over Jake's ass. On another encounter with Neil Jake swallowed Neil's cum. But Neil had to help by jacking off. On another encounter Jake gave Neil a handjob and brought him to orgasm. But that wasn't as satisfying as Jake had imagined. Jake was tired of fantasizing and was starting to convince himself that he owed it to himself to go through with it. Neil was the man who Jake trusted most and he deserved to be treated like a king after putting up with the endless emails over the years. If Jake was going to let a man cum in his mouth, he was going to make sure it would be an experience this lucky man wouldn't soon forget!

Years ago Jake had chosen the name Lindsey for his feminine name. Neil was more into masculinity but didn't mind if Lindsey dressed up as long as his manhood was taken care of. Lindsey emailed Neil and asked if she could come and see him. She knew he would be expecting a handjob but she wanted to surprise him with what she had planned. Lindsey hopped in the shower to make sure she was clean and ready for what was to come. Lindsey began to feel anxious while in the shower but was tired of not knowing what it was like to try something she had been fantasizing about for so many years. She told herself it was now or never and tried her best to resist the fear of something bad happening. She told herself that if he replies then she was going to finally know what it was like to give all of herself to a man for his pleasure.

Lindsey anxiously got out of the shower and dried herself off before changing into her boy clothes. She would dress when she got over to Neil's house. Part of Lindsey was really hoping that Neil didn't respond. Lindsey was scared but managed to log into her secret email and there it was, a message from Neil. Lindsey's heart was pounding now and her mind seemed to shut off when she clicked to open the message which had only one word, "Now". Lindsey grabbed her bag and walked out the door still in a mind fog. She didn't even remember the drive over to Neil's but before long she had arrived and allowed herself to remain in a fog until she knocked on the door.

Neil answered with a smile and gestured her in. Lindsey felt safe with Neil and the fog was beginning to clear. Lindsey smiled and entered the home before Neil locked the door behind her. Still silent, Neil began to walk through his living room towards the hall that lead to his bedroom. Lindsey knew this was her cue to follow but she had a surprise for Neil this time. Normally when Lindsey would visit Neil he would get to his bed and remove his clothes quickly. Part of Lindsey's fantasy involved removing a man's clothes for him. She also had been wanting to try teasing him with a little playful sucking through his boxers to get him hard before sliding his underwear down to reveal a happy penis. Lindsey wanted to try as many of the erotic acts that had played out in her lustful mind over the years and she wanted to build Neil up to an orgasm she hoped he would not soon forget.

Before Neil could get himself naked Lindsey put her hands on his hands which were at the elastic band of his underwear ready to remove. Not saying anything, and keeping eye contact, Lindsey lifted Neil's hands above his head and pulled his shirt off. Lindsey moved closer and put her arms around Neil leaning in to gently kiss and suck on Neil's neck while caressing his chest with her hands being careful not to get to close to his package just yet. Lindsey continued kissing and sucking down Neil's chest to one of his nipples taking it into her mouth and sucking gently while flicking her tongue across it then moving over to give the other nipple some attention.

Lindsey could see that Neil was enjoying the attention and was herself pretty hot by now. Resisting the urge to drop down to her knees and taking Neil's hardening manhood in her mouth took all she had but Lindsey was going to make this visit special. Continuing her kissing down his belly until she was on her knees. Neil was standing in anticipation, still in his boxer shorts. Lindsey could see his fully erect penis bulging through his underwear. Without using her hands she gently put her mouth on the shaft of Neil's cock and began applying light pressure as she sensuously stroked it with her lips making sure to get his boxers extra wet with her warm saliva. Lindsey's wife has done this to her during blowjob foreplay in the past. That first sensation of warm wetness seeping through your underwear becomes an erotic reminder as the warmth starts to cool. Lindsey slid her hand up Neil's leg grabbing his shaft through his boxers to get the head of his dick in her mouth to suck on making sure it was sopping wet with her warm saliva.

Lindsey withdrew her mouth from Neil's boxers looking up seductively before getting up to take a shower and change into her gurly clothes. Lindsey stood up and turned away from Neil unbuttoning her pants and walking out of them then pulling off her shirt so Neil could see her naked ass as she walked to his shower. Lindsey started her shower and started quickly rinsing off believing that Neil would wait in bed enjoying the cool sensation of her cooling saliva on his boner but as she was soaping Neil came in to watch and he was now holding his phone recording Lindsey naked in the shower. This surprised Lindsey but it was also quite a turn on to her. Lindsey soaped herself as sexy as she knew how turning and bending in different angles to give Neil a good show. Lindsey wasn't going to waste an opportunity this time. She turned to face Neil then slowly dropped to her knees out of range of the shower water and still covered in bubbles. Looking into the camera she quietly said, in a lustful voice, "Pee on me daddy"! Neil didn't waste time and, still recording, stood up and walked over to Lindsey before pulling his half erect dick out through the slit in his wet boxers then took aim. Neil began pissing on Lindsey's face, her mouth opened to eagerly receive his golden stream of hot man pee.

When he was finished Lindsey swallowed what was in her mouth then seductively licked her lips before asking Neil if he would like to join her. Neil kicked off his boxers and entered the shower behind Lindsey pressing his package into her soapy butt cheeks while he ran his hands over her soapy body making his way down to fondle Lindsey's aching hard dick, swirling her precum on the tip while he kissed her neck. Lindsey couldn't take anymore and didn't want to cum yet. She turned to face Neil hoping he would let her kiss him. They locked in a deep kiss while Neil's strong hands squeezed both of her butt cheeks firmly, Lindsey's hand gently pulling on his cock.

Neil broke away from the kid and said "suck my dick" and without even thinking Lindsey dropped down and plunged deep on Neil's hard meat sucking as she came back up to the tip swirling her tongue before plunging back down this time bottoming out taking him to the base of his dick. Lindsey felt so sexy on her knees loving on Neil's dick but she wasn't ready to let Neil climax just yet so she slowly withdrew her lips from his shaft while keeping eye contact while she moved down to work his balls a little to let him cool off a bit. While very gently sucking and licking his balls Lindsey remembered that Neil had asked her if she would rim him years before when they first met. Lindsey wasn't ready then but figured this would be the perfect opportunity to explore going down there while giving Neil some extra pleasure she hoped would be rewarded for when she was ready to bring Neil to orgasm.

Lindsey put a hand on each of Neil's hips and helped turn him around so that his rear was now at her face. Lindsey started by gently sucking on the inner rounds of his butt cheeks, teasing him with a little of what was to come. After a little foreplay Lindsey could hardly wait to dive right in and taste this man's ass. Lindsey parted his cheeks with her hands then leaned in taking a mouthful of his cheek and sucking his way over to Neil's asshole continuing to suck while moving her tongue over his hole. Noel pushed his ass back hard in Lindsey's face to show his approval of her efforts. Lindsey was now thrusting her tongue in and out of Neil's ass while sucking around it with her whole mouth and gently pulling his cock. Neil suddenly grabbed the hand that was stroking his dick and pulled away from Lindsey's face then without an explanation turned off the shower, grabbed the phone that was still recording and walked back into his bedroom to make himself comfortable while Lindsey remained in the bathroom to make herself pretty and change into the outfit she had chosen to finally have a real experience as a dick pleaser.

Lindsey dried off and slid into her black lacy thong then her camisole. She paused for a moment to be sure her legs were dry before pulling on her thigh highs and strapping up her garter. While getting dressed Lindsey couldn't believe what she had already done and what she was getting ready to do. She was very turned on and there was no worries in her mind. She was finally ready to enjoy bringing a man to orgasm. Lindsey knew from a past experience with Neil that it is easier for him to cum from a blowjob than by sex which was ok with her but from that first time they met when Neil penetrated her however briefly, she had an empty feeling the following dates when he didn't penetrate her. He felt so good inside of her and gave her a fullness that seemed important for making her feel like the slut she wanted to be for her man. Lindsey daydreamed about how pretty she was going to look when she surprised Neil with a quick fuck in between edging him with her mouth before finally bringing him to an explosive orgasm both of them would remember. It was time to get out there. Neil was waiting. Lindsey slipped into her little red miniskirt before exiting the bathroom to join Neil in the bedroom.

Lindsey found Neil laying on his back in his bed with his hands under his head. His dick was rock hard and there was already precum dripping from the tip. He knew Linsey was there to spoil him and she planned to do just that. Seeing that he was hard and knowing that Neil enjoys strip teases more than he likes men in woman's clothes, Lindsey thought she would treat him to a little tease. Lindsey started in front of the bed just turning slowly so Neil could gaze on the body that was about to be given to him for his sexual pleasure. Turning around Lindsey seductively stuck her ass out to wiggle her skirt down to reveal her thong clad ass then wiggling the skirt back up just to lift her skirt to show off her ass.

Then slipping the skirt down leaving her in her garters, thong and camisole. Bending over, Lindsey began to unsnap her garter belts one by one then unrolling her thigh highs one, then the other still bent over with her ass pointing in Neil's direction. Lindsey hoped Neil was turned on by her body and couldn't wait to claim his prize. This was her first time actually going the distance with a man and she wanted Neil to feel about her the way a man feels about a naked woman except Neil was more into masculine men than fembois. Now Lindsey was rock hard and making a mess of her panties with her precum. She wanted Neil to see how excited she was and stood up straight to face Neil before pulling down her panties to expose her fully erect boner.

Lindsey couldn't wait any longer, it was time to throw off the gurly clothes wearing only her black lacy thong. Turning back around to give Neil another look at her rear, she pulled off her camisole and tossed it over to cover Neil's crotch adding a pinch of femininity to what was soon coming. After stripping down to her panties Lindsey moved on to the bed straddling Neil with her ass facing him to give him a closer look at her nakedness. Lindsey allowed her balls to fall out of the thong while she seductively moved her hips from side to side. While she was doing this she began to use only her tongue to lick Neil's shaft and balls, switching between gently sucking the tip and licking his package.

Lindsey could hear what could only be a bottle cap being flipped open and she could tell Neil was up to something but couldn't yet put it together being preoccupied edging his manhood. Still shaking her booty softly, now more out of instinct than for show, suddenly she could feel Neil's finger gently circle her sphincter with a lubed finger before gently inserting it to finger Lindsey's ass. This didn't feel like fingering though, it felt more like Neil was trying to spread the lube on her insides while at the same time trying to get her ass used to something larger. After a minute Neil removed his finger and Lindsey could hear the bottle of lube being snapped open again. Before long Neil was inserting three of his fingers which were soaked in lube. Lindsey was surprised this wasn't hurting her as she was aware that her sphincter had now relaxed and Neil's fingers were gliding effortlessly in and out of her. Lindsey was in so much bliss she didn't realize that she had let her lips slide down to the base of Neil's cock sucking him like a mindless cum slut gobbling up Neil's meat.

Lindsey still had an empty feeling in her rear. This date was almost perfect but she wasn't going to let Neil cum before she got a chance to fill that empty feeling with his dick deep inside of her. Lindsey began to crawl forwards until her bottom was positioned over Neil's crotch before positioning herself for reverse cowgirl grabbing his cock to guide it to her well lubed and eager asshole. Just like the last time when Neil briefly penetrated her years earlier, Lindsey was surprised how effortlessly he slid all the way into her until she bottomed out coming to rest sitting on his lap facing away from him. Lindsey wanted to enjoy this sensation, wiggling while bearing down to get as much of Neil as she could. The two sat there motionless for a minute enjoying the sensation of complementing each other sexually before Lindsey began to slowly leaned forward riding Neil so he could see himself bone while he enjoyed his pleasure.

When Lindsey tried to go faster she was afraid Neil would slip out and she would hurt him on the way back down. Lindsey didn't have experience as the receiver so she asked if Neil would fuck her doggystyle. Lindsey also wanted to know what it was like for the man to be in control during sex. Neil agreed and Lindsey got herself into position on all fours while Neil got himself in position behind her. In one quick motion Neil buried his meat balls deep in Lindsey before he began thrusting deep and hard into Lindsey's almost virgin hole. To Lindsey it felt like Neil was hammering at her guts with his rod but she knew this is how a man likes to fuck which helped the slightly uncomfortable feeling turn into bliss. It turned her on that Neil was enjoying himself and while he saw her as a man, in her mind she felt so womanly being used for her man's most intimate pleasures.

It was time to finish Neil off and finally get her reward. Lindsey crawled away from Neil's thrusting turning around to lay her head over the edge of the bed. Neil took the cue and pointed his cock at her lips before pushing all the way down her throat before she even realized it. Neil held himself like that for a bit to let Lindsey get used to what was coming next. Neil withdrew to the tip then smashed back down pausing once again but this time he began thrusting in and out of her throat. It didn't take very long and after a few more deep thrusts Neil pushed deep into Lindsey's throat with her nose buried in his flesh while he let out a roaring moan like he was emptying his soul into Lindsey's belly. Lindsey had no choice but to keep gulping until she could feel him relent and ease up signaling the end of his climax. Then Neil withdrew his dick from her throat bringing with it a little of the residual cum and saliva. While his dick was still dangling there quickly becoming half limp Lindsey took one more mouthful of it to suck him clean to taste his cum.

Neil slumped forward into bed exhausted. Lindsey composed herself and got dressed back into her man clothes before quietly leaving while Neil drifted off for a nap, satisfied with his empty balls.