Femboi has First Time Anal


Jacque was coming over and Ryan waited in anticipation. Finally he heard a knock on his apartment door. Opening the door he greeted Jacque for the first time in months. Both were starting college. They gave a hand shake and a hug to head and shoulders, with a hand around each others back.

“How are you?” Ryan wanted to know.

“Fine, you look as good as ever,” Jacque said as Ryan’s long blond hair flowing over his hand on the back. Jacque could smell an attractive perfume, he wondered if Ryan was wearing perfume. He lifted his hand up through Ryan’s hair and felt it sift through his fingers. He could tell Ryan was as clean as a dinner plate. Ryan seemed to draw closer.

“Isn’t it hard to believe we are both in college now,” Ryan posed the question chuckling.

Ryan brought out a couple wine coolers.

They drank and chatted.

Ryan brought out two more wine coolers, and lit up a marijuana joint.

Jacque asked, “Is that perfume I smell?” He gave a side hug and leaned over Ryan’s neck to sniff.

Ryan said teasingly, “That’s for me to know and you to find out!”

They were starting to get a little high. Teasing back, Jacque hugged Ryan from behind. It felt good to Ryan. He held Ryan around the stomach and held a joint to his mouth to suck a lungful. Looking down he could see Ryan’s pants didn’t quite cover his ass crack, and it looked like there was a dainty panty band. Ryan’s shirt didn’t cover all his back, and all the bare skin and long hair started to turn Jacque on.

Ryan took a big draw on the joint letting his lips touch Jacque’s fingers in the process. He took another drag and gave the slightest lick on the fingers. Also, he gave the slightest wiggle of his butt against Jacque.

Jacque let his hand drift from around the stomach up and under Ryan’s shirt in the front and squeezed a tit like they had joked about before. Then he let his hand travel down his stomach until there was the slightest peach hair below the navel and just where the hair grew a little more dense he let his hand drift over the band of his pants just close enough that he could feel the tenting of his pants start to form.

They drank a couple more wine coolers, and Ryan said, “Hey let’s go in here I want to show you my set up.” Ryan led Jacque to his room and turned off the main light. Then he turned on a black light. The whole room lit up in bright black light colors.

Ryan had already set up a night vision video camera, the same as the one he had affixed in the living room.

“Wow!” said Jacque as he noticed things around the room that shown brightly in the black light, including the bed spread, and some of their clothes.

“Let’s smoke this,” Ryan said as he lit up another joint. He had secretly spiked the joint with cocaine. He knew Jacque would enjoy it and it would be a surprise.

After a couple more wine coolers and a couple of the special joints, they were both in good humor and were even less inhibited with each other.

Soon Jacque lifted Ryan’s shirt from behind, and pulled it off.

The exposed bare skin felt good to Ryan.

Jacque stroked and sifted his hand through Ryan’s hair from behind. He let his hand drift down his sides and down his hips. He then traced the band of the hip hugger pants noticing the delicate band of his underwear was panties and shown brightly in the black light. “Let me get a better look,” he whispered into Ryan’s ear letting his tongue skirt the edge of his ear. Reaching around he unfastened the pants and when they loosened up he pulled them further down his hips revealing the colorful panties in the black light and discovering they were silk panties.

Feeling the panties over his butt cheeks and ass crack, Jacque whispered in Ryan’s ear, “Are you wearing panties? These are so smooth, I would love to rub my face on them.”

Jacque was fascinated by the smooth and soft feel of the low rise silk bikini panties. He pushed the pants down Ryan’s legs to get a better look and feel of the panties. He let his hand push down Ryan’s ass crack and it was like there was nothing between the skin of his hand and the bottom of his ass crack. Jacque felt below the rounded bottom of Ryan’s ass cheeks, and around to the perineum and up to the asshole. He could feel the indention of the asshole and the heat from it.

Jacque slipped his hands around from the ass cheeks to the front of the panties and felt every detail of Ryan’s cock and balls through the silk panties.

Ryan felt Jacque feeling his butt, back, and crotch. It was making him horny and he felt Jacque’s hand feeling every part of his cock and balls. Then he felt Jacque’s hand slip under the band of his panties and felt the warm skin of his hand caressing and fondling his cock and balls. He felt the fingers run through his pubic hair, and tease the hair on his balls. He felt the hand and fingers reach all the way back and below his balls. Momentarily he felt a finger rest and push on his asshole.

Jacque had no inhibitions and pushed Ataşehir Travesti on the perineum and prostate gland, and had a desire to finger massage the prostate, but not yet.

Jacque pushed the neon pink and baby blue with rose print panties down slightly and got a wonderful view of Ryan’s ass crack from above enhanced by the delicate band and the color of his panties.

Ryan remembered fond dreams about Jacque, as Jacque was feeling him off.

Briefly Jacque sat Ryan down and pulled off his shoes, white stockings, and pants. He noticed the white stockings shown brightly in the black light. He noticed how cute Ryan’s smooth hairless butt was. He stood Ryan up again and cupped his ass cheeks, then ran his hand up and down his crotch teasing balls and asshole.

Ryan lit up another spiked joint and noticed they both had hard ons. He went to get another round of drinks, and brought back a cold can of Reddi whip cream.

As Jacque toked on another joint, Ryan facing him in the front unbuttoned his shirt and took it off pushing it down his arms and to the floor. As he unbuttoned the shirt all the way down, he unfastened Jacque’s belt buckle and pants purposely nudging the hard cock up and down. As he loosened the pants he noticed Jacque was wearing white cotton thong panties that shined brightly in the black light. Ryan asked, “How long have you been wearing panties? I never knew.” He didn’t have to wait for an invitation and pulled down the pants. Removing the shoes, he helped Jacque out of the pants, felt his crotch and pulled his thong all the way off. Now they were both totally naked.

Jacque was still smoking the large joint as Ryan hugged him from the front squeezing his naked body against Jacque. Ryan reached around and held both of Jacque’s ass cheeks and pulled him tighter against him. Their cocks were rubbing in frottage. Ryan fondled the entire roundness of the butt cheeks, and ran his hand up and down the crack. He felt the asshole and the back side of his balls, and the top of his legs. He loved caressing the hair on the back of his legs and feeling the strong leg muscles. Pulling up from the top of the legs and the bottom of his butt cheeks, Ryan felt the firmness of Jacque’s butt. He let his hand caress up his spine to the base of his neck, then kissed his neck and let his tongue follow the jaw line, and up to the edge of his lips.

Jacque already had his lips pursed from smoking the joint, and when he took the joint out for a second, Ryan licked his lips wet and planted a kiss on him, before kissing his cheek.

Ryan said, “I have another surprise for you.” He took the can of Reddi whip and made a circle of the whipped cream around his tits. In the black light the cream shown brightly, and without hesitation, Jacque licked and sucked up the cream, tasting and licking Ryan’s nipples. The cold Reddi whip and the wet tongue felt sensational and his nipples stood out.

Jacque and Ryan took turns snapping pictures to go along with the video.

Twisting around, Ryan then put the whipped cream on the contour of his ass cheeks displaying his wonderful cute curves in the black light.

Jacque got on his knees and erotically licked the cream off Ryan’s butt. Then he passionately sprayed the cream into Ryan’s crack and all the way down to his crotch and the back side of his balls, a under the curve of his bottom at the top of each leg, and then all the way up his spine to the small hairs on his neck and the outer edges of his ears. Then he started licking it all up, starting with the crotch.

The Reddi whip and the open air made Ryan even more horny.

Jacque licked the cream from the bottom and then started up the crack. He spent quite some time licking it off the ass hole, and rimmed it good, tickling it until Ryan squirmed.

Jacque covered Ryan’s entire ass with Reddi whip and using his tongue made a smiley face on both of them. He took a picture of the smiley face butt cheeks with the Reddi whip glowing white in the black light.

The Reddi whip and the licking of his asshole made Ryan super horny.

Licking the ass crack clean Jacque licked all the way up the spine in a tantalizing way until he was licking the small hairs at the base of Ryan’s neck. It was driving Ryan crazy. Then he licked the cream off his ears and Ryan almost came right then.

Jacque ran his hand up and down Ryan’s crack pushing and feeling his ass cheeks from side to side, and squeezing them.

Ryan then took the Reddi whip and circled his own lips with it and then coated Jacque’s cock and balls with it. In the black light Jacque could see his cock pointed at Ryan’s white ringed open mouth. Ryan was on his knees with mouth open and under the black light Jacque was turned on strongly by the sight of his white cream covered cock sliding into the circle of Ryan’s lips. He took pictures.

With the creamy covering Jacque was surprised that the head of his cock slid right into Ryan’s throat, deep throat, and Ryan was licking Anadolu yakası travesti the cream off of his balls.

The sensations were too great and Jacque grabbed the back of Ryan’s head and held his cock all the way in while shooting cum in great spurts down his throat. It was Ryan’s first time deep throat and the Reddi whip made it easy and natural.

Ryan held onto Jacque’s ass while he was bucking in his throat. He caressed and fondled every inch of the ass, adding to the sensations Jacque had.

As Jacque pulled out, a good helping of cum strung across Ryan’s tongue, and it tasted delicious, mixed with the Reddi whip cream.

Now Jacque had Ryan lay his stomach over the edge of the bed. The smooth cute hairless butt was almost too much for him and his cock was already getting hard again. He sprayed more Reddi whip in Ryan’s ass crack, and licked it all up giving special attention to giving an unforgettable rim job. He had noticed Vaseline on Ryan’s dresser and reached over to get some and lube Ryan’s asshole good. While he fingered Ryan’s asshole he also massaged his prostate until pre-cum was leaking profusely from Ryan’s cock that was pulled toward the back and down the side of the mattress. With his other hand he harvested some of the pre-cum and brought it to his mouth. It was a salty treat, and tasted good.

Ryan had never been fingered in the ass before and it felt surprisingly erotic. The sensations to his crotch and cock from Jacque turned him more and more horny.

It shouldn’t have been a surprise, but soon Ryan felt a smooth knob at his asshole replacing the fingers. He felt it push against him, and he gamely pushed back a little. He was relaxed due to the drinks, and joints. With small pumping motions, and a little pressure, Ryan could feel the cock head, as he now realized, start into his asshole. He didn’t think it would fit. Jacque was gentle and slowly kept working it in.

Ryan felt the head of the cock work past the first sphincter and push against the secondary muscle of his asshole. He felt the flange of the cock head spread his opening. He felt the heat of it. Then he felt the throbbing of the shaft.

Soon enough Ryan felt the shaft of the bareback cock in his ass. He actually felt the cum vein pulsing in the passage. Jacque let Ryan’s ass adjust to it and relax before pushing more. This kept up until his pubic hairs were against Ryan’s crotch.

Ryan reached around back and down his crack until he could feel the cock sliding in and out all the way. Then he reached between his legs until he felt Jacque’s balls and massaged them against his crotch and balls.

This was the first time Ryan ever had a cock in his ass, and was glad it was Jacque fucking his ass for the first time taking his anal cherry.

“Do you like it?” Jacque asked.

“Love it. Fuck me, please fuck me. I never knew you would feel so good in me.”

They both came at the same time. Jacque left it in until it softened, almost falling asleep on top of Ryan’s cute butt. Finally his cock softened and came out on its own. He saw a little dribble of cum come out of the edge of Ryan’s asshole. He took a finger and spread it on Ryan’s inner ass cheek working it into the skin until it melted away.

The immediate memory and feelings of what he had just experienced made Ryan’s cock start to get hard again. They had another spiked joint, and soon it was at full strength. Ryan pushed Jacque’s naked stomach over the mattress with his knees spread on either side of the corner of the mattress giving an arch to his back.

Ryan slowly fingered Vaseline into Jacque’s asshole with one hand while feeling his ass crack, butt cheeks, crotch and balls with the other. He worked in the lube with loving care, then rubbed his cock up and down Jacque’s ass crack fascinated by the feel and the firmness of the butt cheeks. He kneaded and felt off the butt cheeks. He loved the feel from the top of the legs to the bottom. Then he felt of the crotch loving the feel of the skin at the back of the balls, the exotic perineum skin, and the wrinkles surrounding the asshole in a starburst pattern.

Ryan pushed his cockhead against the asshole feeling how firm the opening might be. It felt warm and pliant. He made a small circling motion with his cockhead while pushing and saw the tip of his cock had made a dent. Applying more lube he pushed against it more which pushed the lube in for a generous coating.

With anticipation and suspense, Jacque was arching his back, and trying to open his asshole. Feeling Ryan’s cock against him he started to push back in pulses.

Ryan did not have to work too hard to get it started in. Once the head went in he started in a spiral pattern.

Jacque felt the head go in. This was his first time with a cockhead in his ass and it felt good. He was fascinated, and glad it was Ryan’s cock.

Working in a spiral motion, Ryan teased and tantalized Jacque and finally sank all the way in.

Jacque felt Bursa Travesti the pubic hair tickling against his ass, and it felt awesome.

Ryan felt Jacque squeeze and pump on his cock. It was the wildest thing he had ever felt on his cock. He felt his balls slam against Jacque’s crotch, which had felt real good on his hand and now against his balls. He slapped Jacque on the ass and watched it jiggle. He ran his hand up and down Jacque’s ass crack while pumping in his asshole. It felt like it was made for him.

Ryan flexed and hunched until he finally shot his load into Jacque with strong volleys of cum.

Jacque said, “I can feel it hit my insides.”

Ryan whispered in his ear, “I used to dream of this, and now it is reality.”

Jacque said, “I dreamt of it too.”

Still inside him, Ryan licked Jacque’s jaw line, and then kissed him on his puckered wet lips.

They both felt fulfilled and had a sense of completeness.

The both cleaned up in the bathroom. They had more drinks, and smoked some more joints. Jacque had dreamt of tasting and swallowing Ryan’s cum, and now he was on his knees in front of Ryan and sucking his cock. Ryan had reenergized while they had taken a break to clean up but now got hard again. Jacque licked and sucked cock and balls. He loved the feeling of Ryan’s hairy balls in his mouth, and loved the spongy feeling and he intricate taste of his cock head. He licked up and down the shaft tasting the cum vein, and feeling his tongue push on it feeling it fill out again.

He could feel Ryan’s pulse with his cock between his warm lips.


Ryan took art classes at the college. He had a taste for artistic subject matter and how to get the right contrast and angle in a picture. Being artistic, Ryan had taken snap shot from the video with Jacque. Ryan painted the scenes based on the video and photos.

One painted pose was of cock sucking with a Reddi whip covered cock and a ring of Reddi whip around the mouth. He painted another pose with a knee up and ass twisted and arched exposing the asshole. He painted another of a cock entering the asshole. There were poses of licking ass crack, and of sucking balls. He painted them all. They were paintings but there was an element of privacy, usually not showing the face or changed in some way as not to distinguish who was in the painting.

Ryan took the paintings to school one evening after classes and went to see his art Professor. Professor Winstead was a liberal, and a straight married man. He looked up as he heard a knock at his public office door.

“Come in.” He saw Ryan, one of his students, come in the door with a canvass carrier and some paintings. He noticed Ryan had some feminization, dressed in worn hip huggers that showed the top of his ass crack, and so low in the front he saw a fluff of pubic hair. Ryan was wearing a cropped shirt with his entire stomach exposed up to and almost showing his nipples. He wore a choker, and his long hair was brushed and hung down his back below his shoulder blades. Both at the front pubic hair showing and down his ass crack in the back, Professor Winstead could see the delicate band of panties. In the front they looked like silk panties.

“Hello Dr. Winstead. I would like you to see my paintings. I am dying to see if you like them.

Ryan took out the first painting, and introduced it. “This depiction is under a black light setting and the bright white cream is Reddi-whip glowing in the black light. The subject matter of the painting in the center is an open mouth with a white cream circle around the lips, and a cream covered cock entering the mouth. You can see the tip of the tongue in readiness.”

The Professor was looking at the kinky painting intently and with concentration. Ryan could see he was really interested in it.

Dr. Winstead asked, “Is that you?”


Ryan could see the lump growing in the thin slacks of the professor. The distinct shape and size of his cock was easy to see. Ryan thought it looked good.

“Let’s see the others,” Dr. Winstead said with enthusiasm. He liked the one with the knee up showing a beckoning asshole.

Ryan could see his cock was straining his pants now.

After seeing the painting of the cock entering the asshole, Dr. Winstead asked, “How realistic is this painting?”

“I can show you,” answered Ryan.


Dr. Winstead watched as Ryan turned to put the painting back in the carrier. He could see all the skin on his back, and the slightly tanned top of his ass crack, with a little more of the panties showing. The combination including the panties, caused him to drip pre cum in his pants.

Ryan stood in front of the sitting Professor. Now Dr. Winstead could see the expanse of his stomach so close to his face he could reach out and lick it. He saw the trail of peach fuzz leading down to a crop of pubic hair above his zipper. He wanted to see how accurate the painting was and watched with anticipation as Ryan started to unzip and unfasten his pants.

Ryan slowly unfastened his pants as he sashayed his hips a little to help shimmy the pants down.

Dr. Winstead watched with mouth watering interest, as the pants slid down slowly in sexy motions. This exposed Ryan’s panties. “Those look smooth.”

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