tagTranssexuals & CrossdressersStrangest Bedfellows

Strangest Bedfellows



Donna woke up that Saturday morning as she usually did, horny and in need of an orgasm. At 43 years old she missed the morning sex that she used to have with her boyfriend. Donna was widowed and financially set for life but because of that she didn't not keep steady beau around. She took her trusty dildo from the nightstand and eased into her pussy. As she fucked herself with the fake cock she spotted her favorite toy in the bed. She had used it the night before when she was in the mood for both vaginal and anal sex. It was a double dildo with a handle on the end and it could fill both holes simultaneously.

Her bedroom door was locked as she quietly plunged the dildo in and out of her pussy. She loved the way it rubbed her g-spot and her clit at the same time. Donna was careful not to give away her masturbation activities to her 19 year old son who was home from college. As she worked toward her first orgasm of the day she pondered her handsome son. He had never dated in high school and he was tight lipped about his social life at school. Ethan was attending a very expensive private college majoring in music. Donna could afford the tuition as she had well provided for by her deceased husband.

As Donna continued the assault on her pussy, Ethan was in his bedroom jerking off. His thoughts were on his piano coach who would be there later that day. Donna reached her climax and she covered her mouth with her forearm to stifle her moans of ecstasy. She drenched the dildo with her love juice as he body shook with pleasure. In the other bedroom, Ethan ejaculated and shot several streams of cum into the air that landed on his chest and abs. he continued to masturbate squeezing every drop from his cock. Donna removed the fake cock from her pussy and licked it clean. She loved the taste of herself. Likewise Ethan licked the semen from his hand.

Donna eased her lovely naked body out of bed and checked herself out in the full length mirror. She liked what she saw and she should as she was very fit and shapely. There was slight sag to her small breasts but her hot looking ass was as firm as ever. Donna had one of those asses that was made for butt fucking as it seemed to reach out for attention. At 5'6" tall and 130 pounds she was still very desirable sporting a 34-26-36 figure. Her long brown hair made her look younger than 43.

Ethan had got out of bed and went to the bathroom to take his morning piss. He loved to pee right after cumming as he still felt sexy. He liked playing with his cock which was just a bit larger than average. As he washed his hands he checked himself out in the bathroom mirror. He liked himself and the way he looked. He had wavy brown hair but a virtually hairless body. His skin was flawless without a blemish. At 5'7" he weighed a fit 150 pounds and his body was toned from all the swimming at home and school.

Donna and Ethan both got dressed and went downstairs where they met in the kitchen. They had juice, coffee and cereal for breakfast. Over a second cup of coffee they discussed their plans for the day. Donna was going to the country club later and Ethan's piano coach was coming over later. Donna planned to be gone while Ethan practiced the piano, not that he played poorly, she just wasn't a fan of classical music.


Danielle, Ethan's piano coach, arrived minutes before Donna left for the club. Danielle, who liked to be called Danny, was a pretty blonde with long flowing hair. Danielle was small breasted but like Donna, had great legs and a killer ass. That day Danielle wore a blue mini skirt with a matching blue jacket, a white blouse and white hose. Danielle always looked good but that day particularly sexy and desirable. Donna liked Danielle who was 24 years old and she often wished that Danielle was younger and had hooked up with Ethan.

"I'll see you later Ethan and you two behave," Donna teased as she left the house.

Donna was on her way to the club when she realized that she forgot to bring the items for the women's meeting. She was only ten minutes from home so she turned the car around and returned to the house. Twenty minutes was all Ethan and Danny needed to get started and when Donna returned home Ethan was already fucking Danny. Donna was not quiet when she entered the house but Ethan and Danny were so pre-occupied that they never heard her.

Donna turned the corner to head upstairs and she was about to speak to Ethan when she saw the two of them. Danielle was kneeling on the piano bench and bent over the piano. The blue mini skirt was pushed up and the panties had been removed. Ethan had his pants and underwear around his ankles and he was fucking Danielle from behind. Donna was stunned at first and then pleased. Suddenly she was proud of her son whom she had had doubts about. Donna watched them for a few minutes as they were facing away from her.

Donna then walked quietly upstairs and positioned herself so she could watch them from the balcony. It was then that she saw that Ethan was fucking Danielle in the ass. She thought who could blame him as Danielle had a beautiful ass, just the kind one would want to fuck. Donna pulled up her skirt and pushed her hand into her panties. She didn't care if she was going to be late for the meeting as she enjoyed being a voyeur. Ethan had a nice cock, above average but not too big and Danielle apparently loved it in the ass.

Ethan picked up the pace fucking Danielle who encouraged Ethan to fuck harder and faster. "Go you Ethan," Donna thought to herself as her fingers flew over her clit and she was close to an orgasm. Ethan suddenly made one final thrust and stopped moving with his cock buried to the hilt in Danielle's ass. Donna knew that her son had cum in the piano coach's ass and it sent her over the edge. Donna covered her mouth to muffle her gasp as a climax rocked her body.

As Donna slowly recovered from her intense orgasm and she watched as Ethan slowly eased his cock out of Danielle's ass. He remained hard and Donna wondered if he would fuck the piano coach a second time. Ethan stepped back and Danielle turned around and sat on the piano. Donna had to stifle another gasp but this one was in surprise. As Danielle turned over Donna saw another erect cock and this one belong to Danielle and what a cock it was. It was clearly bigger than Ethan's and one of the biggest that Donna had ever seen in person.

Donna now knew that Danielle was a transsexual but she couldn't get over the blonde's beauty and feminine appearance. Ethan dropped his head and took the impressive cock in his mouth. Donna watched in disbelief as her son gave Danielle a first class blow job. That scene answered Donna's question about her son and there was no longer a mystery about his sexual orientation. It didn't take long for Danielle to cum and Ethan stayed glued to the big dick and drank down every drop.

Ethan then kissed Danielle and spoke loudly enough that Donna overheard him. "Come on let's go to my bedroom. I want to fuck you again and I want to feel this in my ass," he said as he held Danielle's stiff cock in his hand.

Donna moved quickly to her bedroom and stayed there until Ethan and Danielle made their way to Ethan's bedroom. Donna checked to be sure the door was closed and then she quietly went downstairs and left the house. She got in her car quickly and drove to the club. She could not get the image of Ethan and Danielle out of her mind and she could only imagine what they would do the rest of the day. Donna kept seeing Danielle's large cock and secretly wished that she had access to a cock that big. The guys she had dated lately were more average like her son.

That afternoon at the club, Donna had a difficult time staying focused on the meeting. In a way she was anxious to get home and hopefully see more of her son and his lover. Donna still could not get used to how beautiful Danielle looked and then to be so well hung, it was mind blowing. She tried to imagine her son taking Danielle's cock in his ass and she wondered how he could handle it. Donna had had anal sex many times in her life but with average size cocks not an ass buster like Danielle's.

When Donna got home after her meeting, Danielle had left and Ethan was relaxing in the family room. "Hi mom, how was your meeting?" Ethan greeted her.

"Oh it was the same, no big deal. How was your day?" Donna replied.

"I had fun. Danny is a great coach," Ethan said calmly.

"Yes, I bet she is a great coach," Donna said somewhat sarcastically emphasizing the she part.

"I called out for pizza. It should be here soon," Ethan added ignoring his mother's sarcasm.

"Good, I don't feel like cooking tonight," Donna agreed and then she went up to her room to change.

After pizza, drinks and an evening of TV it was time for bed. Donna went to her bedroom but she had a difficult time falling asleep as the image of Danielle kept creeping into her mind. Ethan on the other hand had no trouble as he was tired and sexually sated. He and Danny had been at it for hours taking turns sucking and fucking each other. They both had the capacity to cum four times a day.


Donna and Ethan had a late breakfast Sunday morning and then Ethan went into the city to spend the day with some friends. Now that Donna knew that Ethan was gay she assumed that her son was hooking up with other gays that afternoon. Donna decided to chill out on her family room sofa with the Sunday newspaper and a Bloody Mary. She wore exercise shorts, panties and a tee with no bra. Donna had been reading the paper for about an hour and she was nursing her second Bloody Mary when the door bell rang. She wasn't expecting anyone but she answered the door and she was surprised when she saw Danielle standing there.

"Danielle, hi, Ethan isn't home. He's in the city with some friends. Was he supposed to have a lesson today?"

"I know he isn't home. I wanted to talk with you. May I come in?"

"Of course, I was just reading the paper and having a drink, come in"

Danielle followed Donna into the family room and spotted the drink. "A Bloody Mary, I'll have one too," Danielle said without being offered a drink.

Donna suddenly felt awkward with the assertive Danielle in the house. "Sure, I'll get you one. I was just about to ask," Donna lied.

Danielle was wearing a mini skirt again which seemed very short and displayed Danielle's lovely legs. The skirt was a tight fit and accentuated Danielle's curvy ass. Donna was still amazed how much Danielle looked like a woman now that she knew the truth. Donna made her guest a drink and returned to the family room. Danielle was already seated waiting for Donna.

"Well this is a surprise, what's brings you here today?" Donna asked.

"I wanted to see you and explain a few things. First of all I know that you know that I am a transsexual. I know that you were watching Ethan and me in the family room yesterday," Danielle began.

Donna turned beet red and apologized, "I didn't intend to spy on you but when I saw you together I couldn't tear myself away."

"It's okay, I'm cool with that but I wanted to let you know that I like women too. I know Ethan is gay but me, I'm flexible or as some say bisexual," Danielle stated.

Donna blushed again, "You like women too, how does that work. Do you dress like a woman all the time?"

"Yes I always dress like a women but I have fun with it. Some women come onto me because they expect to make love to a woman. Boy, are they surprised when they take my panties off," Danielle giggled and then added, "Some are cool with it and some runaway."

"Do you do that to guys too?"

"Sometimes but it depends on the guy. I don't want to get my ass kicked because I tricked some guy who is chasing pussy," Danielle admitted.

"So why are you here telling me all this?" Donna questioned.

"Well I always thought that you were hot but I never came onto you because of Ethan. I let you believe that I was a woman but now that you know I have a cock, things can be different."

"Different, how will things be different?"

"Oh come on Donna, I know that you like sex and I know that you are impressed with my cock. I came here today to make love to you," Danielle said confidently as he moved to the sofa and sat next to Donna.

Donna was frozen to her seat as the pretty Danielle sat next to her and removed Donna's tee exposing her small breasts. Danielle rubbed and sucked the cute tits as Donna remained still as if in a trance. Danielle moved his hand under the waistband of Donna's shorts and panties and cupped Donna's dipping pussy. Donna gasped when Danielle's fingers entered her vagina and probed her gently but she didn't stop Danielle then either. She also didn't stop Danielle when Danielle pulled her shorts and panties down her hips in fact she raised her hips making it easier for Danielle to remove the clothing. Danielle smiled as she looked at Donna's pretty trimmed pussy which he knew was now his for the taking.

Danielle moved between Donna's legs and lifted them up on her shoulders. Donna was breathing hard now in anticipation of Danielle's mouth on her pussy. Danielle did not disappoint Donna as he tenderly kissed the inside of Donna's thighs and worked his way up to the tasty treasure. Donna flinched when Danielle's mouth covered her vagina and then Donna gasped aloud when she felt Danielle's tongue probe her pussy. Danielle's tongue worked its way into Donna's pussy and located her clit. Donna's hips lifted off the sofa when Danielle found the object of desire. Donna's clit was hard and extended and Danielle gently nibbled it and tongued it. Donna was overcome with desire and she knew that her orgasm was fast approaching.

Then Danielle lifted Donna's thighs up and pressed her legs back toward her chest. The move exposed Donna's pussy and anus to Danielle who then resumed tonguing Donna's pussy. Danielle then ran her tongue from Donna's pussy to her nether hole causing Donna's body to shudder. Donna gasped loudly when Danielle dipped her tongue into her anus. No one had ever tongued Donna's anus before and she felt so naughty at the moment. Danielle then slid the tongue along Donna and back into her pussy. Danielle continued to alternate between licking Donna's pussy and rimming her asshole. Donna felt the act was so wicked but so erotic at the same time that she thought that she would explode at any second.

Explode she did as an orgasm of massive proportions rocked her entire body. Donna's body shook with tremors as Danielle feasted on her pussy drinking in every drop of Donna's sweet nectar. Danielle held the back of Donna's thighs and kept them pressed back toward Donna's chest as Donna screamed out loud. Danielle continued to lick Donna's pussy and then Donna felt a pussy moistened finger enter her asshole. For the first time in months Donna's anus was penetrated. Danielle continued to finger Donna's ass and lick Donna's pussy until Donna had another orgasm. This time when Donna came, Danielle popped her finger out of Donna's asshole causing Donna to scream out in passion as she climaxed again. Donna was panting and breathing hard when Danielle lowered Donna's legs to the floor.

Donna couldn't remember exactly the last time that she had cum like that but it had been months. As Donna recovered Danielle licked and kissed the inside of her thighs. Then Danielle stood up and took off his blouse. Donna stared at her new pretty lover who was naked from the waist up. Danielle smiled and then spoke softly.

"Donna, take down my panties," Danielle said almost in a whisper.

Donna knew that she couldn't refuse not after what Danielle had done for her. Donna sat up on the sofa and pulled Danielle closer to her. Then Donna reached under Danielle's mini-skirt and located the panty waistband. Donna tugged the panties down Danielle's hips, they were very snug and they snagged on Danielle's erection.

Donna tugged a little harder and then the panties slipped down Danielle's thighs. As they did Donna gasped in surprise as the rock hard cock sprung out and bobbed in front of Donna's face. Donna was lost for words as she stared at the impressive cock which looked much bigger than it had from a distance. At that moment, Danielle unfastened his mini-skirt and let it drop to the floor along with his panties. He stood there totally naked in front of the astonished Donna.

"Donna sweetie, suck my cock like I sucked your clit. See how big and hard my cock is. You got me so excited, please suck it," Danielle said sexily.

Donna stared at the cock and then took it in her hand. Donna knew that Danielle's cock was bigger and thicker than any she ever had and she would learn later that it was just over eight inches long and almost five inches around. Donna's hand did not close all the way around the thick shaft. As if in a trance Donna moved her mouth to Danielle's cock and took the head into her mouth. Donna liked the soft feel of the mushroom head and she ran her tongue around it and tickled the pee hole. Danielle groaned and his body tensed when Donna's warm sensuous mouth closed around Danielle's cock. Danielle was ready to blow and he knew that it would not take much for him to cum.

Donna was a very good cocksucker and in no time she had Danielle ready to blow his load. Danielle tried to prolong his ejaculation as long as he could. Donna sat on the edge of the sofa and drew Danielle in toward her. Donna caressed the back of Danielle's legs and cheeks of his ass as Donna's warm, wet, wonderful mouth sucked on Danielle's cock. Donna massaged the head of Danielle's cock against the roof of her mouth. She circled Danielle's cock with her tongue and Danielle felt the light scraping of Donna's teeth. Danielle's dick felt hard and long as it always did when this excited and he knew he was going to shoot soon.

Donna took Danielle's cock out of her mouth and looked up at him as she stroked the entire length of it and massaged Danielle's bloated balls. Donna then put it back in her mouth and took it out again then she gently blew on it as her fingers continually massaged Danielle's balls. Donna tickled the cock head with her tongue and teased Danielle's pee slit. Donna had Danielle close to cumming a few times. Donna seemed to know when Danielle was getting close, and she would do things making him last longer, torturing Danielle in the process.

Donna then took Danielle's cock all the way into her warm wet mouth. She swirled her tongue around the length of the shaft, nibbled on the cock head and sucked Danielle hard. Donna reached under Danielle's balls and rubbed the hardness between his balls and anus as she remembered that guys loved that. Danielle felt his cock thicken and he knew he was going to cum. There was no stopping Danielle this time.

Donna grabbed Danielle's ass cheeks with both hands as Danielle exploded in her mouth. Danielle fired round after round of cum into her mouth and Donna sucked and swallowed as fast as she could. Rope after rope of semen shot into Donna's mouth as Danielle seemed to have an endless supply. Finally the barrage subsided and Danielle stopped cumming in Donna's mouth. Donna sucked on the thick firm cock until she had drained every drop from Danielle's dick. Donna was no stranger to massive loads filling her mouth.

Donna sucked on Danielle's cock long after he had finished cumming and Danielle's cock remained hard. Danielle then pushed Donna back on the sofa and crawled between Donna's legs. Danielle eased his still hard cock into Donna's moist pussy and Donna groaned as the biggest cock ever filled her womb. Danielle began to slowly fuck Donna and Donna wrapped her arms and legs around her new lover. Danielle leaned in and kissed Donna deeply seemingly unconcerned that he had recently cum in Donna's mouth.

Danielle was about half way in when she pulled out and then slowly eased back into Donna causing her to moan in pleasure. Danielle would push in a little and then pull out a little slowly working his cock deeper and deeper into Donna's vagina. Finally his entire cock was buried in Donna's pussy and Donna sighed feeling completely full almost afraid to move. This was a fantastic sensation for Donna to be this full. Donna was in a euphoric state and Danielle being a transsexual was the furthest thing from her mind. Donna was now enjoying the same cock that brought her son so much pleasure.

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bywalterio© 8 comments/ 70083 views/ 76 favorites

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