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Click hereOne night Warren was in her bed. He was naked except for a pair of briefs. Barbara was completely naked. She laid on her side next to him, running her hand along his back and letting her erection rest across his bottom. She was just finishing up a story about the time she fucked a door-to-door salesman who couldn't stop staring at her tits long enough to try to sell her on his product. She had wanted the thing that didn't cost a thing from him, his tender, vulnerable asshole. And she took it.
"Why don't you sleep in here with me tonight?" she asked Warren as though she'd just thought of it.
"Yeah," he told her. Warren stretched out on her bed, clearly enjoying the way she rubbed his back.
Barbara leaned in closer to him and blew hot air on his ear. She started to nibble at his earlobe. Barbara whispered, "What would you say if I told you I want to stuff your little ass with my cock?"
Warren turned toward her and Barbara kissed him full on the lips for the first time. Their tongues tangled together as her erection squeezed between their stomachs. "I'd ask if it hurts," he replied.
She licked at his neck and responded, "Mmhmmm... for a while. It feels good too. I was afraid my first time. He was a lot smaller than me too. I'd understand if you didn't want to. But I have to say, I think you'd like it, dear."
"Do it," he whispered.
Barbara didn't say anything. She looked into his eyes and then sat up on the bed. Barbara spread her palms over his ass cheeks. She flipped her fingers into the waistband of his briefs and pulled them down his legs and off. Barbara licked her fingers and pressed it between his cheeks. She covered his little hole with spit. She stroked her cock until it was leaking precum. Warren winced when he felt the warm liquid drop onto his opening. She spread one cheek from the other in her strong hand and pressed a finger into his entrance. His sphincter contracted hard around her finger. She pushed in deep and then slowly drew in and out of his vulnerable wrinkle.
She calmly withdrew her finger and told him, "It's gonna be my cock next. Don't panic." Barbara worked up more precum and coated her shaft with it. She slid past his cheeks and let the head sit at his entrance. "The first few inches are going in fast so it won't hurt as bad for long. It's ok, darling."
Warren felt the tip press into him and then in a flash Barbara thrust her cock through his defenseless sphincter. Warren cried out, clutching at the pillow under him. He felt like she'd split him in two. Barbara pressed her body down on his. Her tits squashed against his back and she whispered, "That might just have been the worst of it. I'll go slow. Oh fuck, you're tight." Barbara moaned into his ear. "I'll go slow..." she repeated again. The feeling was unlike any Warren had ever experienced. His tender insides clutched her pole with everything he had. Barbara was steady, slowly skewering him an inch at a time.
Warren groaned. Finally he felt their bodies meet. Barbara's balls rested against his. She told him, "Get used to it. Your ass is so wonderful, darling. We shouldn't have waited so long to do this." Barbara flexed her womanhood inside him. "Don't think about the pain. Listen to my voice. I know how much it hurts at first. I've had plenty of big rods jammed up my rear end." He gripped her pole even tighter. Barbara grabbed her tits and rolled them around the back of his head. She squeezed his head between them to occupy him while the pain passed. Warren whimpered, mumbling that it was ok to keep going.
Barbara took much care in withdrawing her cock. The inches slipped from his asshole. She pulled out until only the head was left inside him. She humped him gently. The urges she'd developed as a young sexually active t-girl years ago were to impale him and fuck his guts out. She tried to resist them. His muscles squeezed her shaft as she pressed in. The friction her length encountered on the way back in were like fireworks of pleasure for her all going off at once.
She started a string of thrusts into him. Warren's pain started to dull, he had this feeling of alleviation. The pain he felt became something else. It was steadily turning into a new kind of pleasure. Barbara started to fuck him a little harder. She relished deflowering his sweet bottom. Barbara always loved the power it gave her. Having her penis buried inside a man meant they were at her mercy. Barbara groped his young body, digging her entire length into him.
"It isn't so bad, is it? You're doing such a good job, dear. I'm gonna go harder now." Barbara, her cock still buried inside, pulled herself off his body and lifted him by his hips. She started to give it to him doggy style. Barbara's hips jabbed into him. Warren grunted. "Mmmm.... baby... darling... you're taking it so much better than I thought you would." Barbara's thrusts were so deliberate, she was taming and teaching his asshole how to be a good, dutiful fuckhole. "You're as tight as I've ever had. You feel so good... so slippery and tight. I love it." Barbara threw her weight behind a deep stroke and moaned, "Fucking love it!"
"Take me," Warren whispered at first. Barbara pounded him harder. "Take me." he said again. "Fuck me!" His ass took every thick, experienced inch.
Barbara drove her length into him. Her balls slapped against his. She crushed him into the bed and hammered his hole like she hadn't fucked in ages. Warren, for his part, humped his little ass back at her. His butt felt like it was on fire and he needed more. Barbara's thrusts became increasingly desperate. She screamed, "Oh FUCK! I'm gonna cum. I'm gonna fill your ass so deep!"
Warren's muscles clamped down even harder around her girth. He was sweating and so was she. He voiced his pleasure in groans. Barbara buried herself inside him and let out a loud, primal cry of pleasure. Warren grasped the sheets, moaning. He felt his own hard cock start to spew against the bed. Barbara's cock pulsed; her cock hit a spot so deep inside him and then she exploded. Barbara came and came. Warren was completely filled with her love goo.
She collapsed on top of him, her cock continued to spit strands of ejaculate which coated his insides. "That was so damn good. I got you and filled you good," she panted. Barbara had a satisfied smile on her lips. She reached around Warren, who was just recovering from his orgasm, and found the sheet under him covered in cum. She gave his cock a stroke, "You shot your load, too. Mmm..."
Barbara laid on top of him afterward. She kissed and whispered things to him. It was minutes before she finally got off of him and said she'd be right back. Warren turned around on the bed. His ass was sore, but in a lot of ways, it was a pleasant soreness. Barbara was grinning ear to ear when she returned to the bedroom. Warren watched her cock swing between her legs. She had a camera in her hands.
"What's that for?" he asked.
Barbara snapped a photo of him. Then another. "I know you won't be around here forever. You came and that's all the proof I need to know this is the life you're gonna have." Warren's face turned red as he considered the truth to it. "You're going to find a girl your own age who does what I just did. I want things to remember you by." Barbara snapped another photo of him.
He was a little embarrassed at first that she was taking pictures of him with cum dripping from his ass, but then he realized that was exactly what she wanted. Warren started to get more into it. He posed for the camera. Her cock was growing. He wrapped his hands around the shaft and put it up to his face *snap*. He rubbed his cheek along it *snap*. Warren kissed the tip *snap*. He turned around and spread his sticky cheeks *snap*.
***
Warren woke up the next morning in her bed. He could smell breakfast cooking. Warren slid off the bed. A dull ache reminding him of their activities last night. He smiled to himself. Warren groggily walked into the kitchen.
"Good news," Barbara told him warmly. She was flipping pancakes.
"Hmm?"
"My niece is going to spend the rest of the summer with us." Barbara sounded almost giddy. "I told her about you staying with me. Even sent her one of those photos I took of you. I can't wait til you see her cock. She really reminds me of myself when I was younger. We're gonna have so much fun together." Barbara flashed him a big grin.
There were two of them? There were going to be two of them under one roof with him? Warren's legs went weak.
- COMMENTS
JizzzyJay2 months agoSuch a hot seducion story. Warren sounds like the perfect cutie. Not surprised his mother sold him to Barbara.
magic_tantra3 months agoI had a male stud seduce and train me to enjoy swallowing semen then fellatio then anal penetration. The slow fuck I got on my belly in bed as his huge cock skewered me by gravity fucking me from above. Would have been hit with a shemale!
Cuzbro603 months agoI wish I was Warren !! Tongueing her beautiful anus. That big beautiful cock down my throat and thrusting deeply into my puckered anus, breeding me deeply.
I was rock hard reading it, my hole stuffed with my nine inch dong (Imagining it was Barbara's enormous cock). More please.
Jessica_Foxx8 months agoA great story, when are we going to find out what happens when Barbera's niece arrives?
Dexisy10 months agoI loved this story from beginning to end. Well told and the theme is so extremely hot.
It inspires me to write in the same vein of your work. Splendid.
DrDrk_4955about 1 year agoVery, very interesting!!! Only an experienced and mature (person) knows how to be gentle and patient with an inexperienced partner.
A well told story and a follow up chapter or more would be GREATLY APPRECIATED!!!!!! The tales the three of them could tell!!!!!!!
Thank you!!
Anonymousabout 1 year agoWould love the next part of story when the boy does it to shemale’s ass Their assholes are so accomodating and experienced!
Anonymousover 1 year agoFuckin creepy that bitch is a fuckin loser shemale female doesn't matter that's so gross
Anonymousover 1 year agoWell, another fantastic and well written story. Would love to read more recent stories from this author but it has been over a decade since the last story was written. Too bad, very loving author.
Anonymousover 1 year agoThat story reminds me the first time I got fucked in the ass by shemale! it was fantastic!
Jackiemichellealmost 2 years agoGreat story. You've got to finish the story. Need to know what happens and how it ends
Anonymousalmost 2 years agoWouldn't love to hear a side story about her younger days breaking Blake.
Anonymousabout 2 years agoSo hot. Couldn't stop reading. I love women like her. Hopefully they'll be more. Of the story also
Anonymousover 2 years agowow,, this is a super hot story, I wish this wouldve happened to me. Transgurls are definetly my favorite. Please keep writing your stories. cant wait for more.Love you sweetie
literoticmanover 2 years agoDamn... This sounds soooo fun. And then 2? Mmmmm. Wish it were me getting fucked like that.
Anonymousover 2 years agoWhat a nice story just wish Barbara can fuck me for the 1st time in my life,, would to get fucked
Benjamin6969over 2 years agoTo be that lucky young man. I’ve always wanted to find someone like Barbara. I would love to be a slave to her and 4 or 5 of her good friends. Their cocks would go from 9 inches to a whooping 17 monster inches. I would love to take the next size up in my tight ass while I sucked the smaller one. This would go on for days and days. I would be the happiest man in the world. I wonder how much cum a male ass will hold. Any volunteers ?
Anonymousalmost 3 years agoHello Ian new to this ima my girly,side of myself . Iam 19yrs old I just brought some bridal pantie and. Stocking and bra and tartar with a white dress. For my first date I hope I will have alot fun too. I cannot wait to. Taste that sex
ShortyMacabout 3 years agoPlease continue with this awesome storyline is hot even tho its so outrageous.
Peeking77about 3 years agoAhh, reminded me of my nature friend. While she did not have a sick she loved sex. She introduced me to pegging. We would go shopping for my panties and brad. She always wore her fill and off times fucked me in dressing rooms. She was a wonderful friend.
Anonymousabout 3 years agoI loved it! I am hoping you will write another part with the niece staying
sissyboi69Aricabout 3 years agoI love this story. I want to find a woman as wonderful as Barbara. Thank you SugarandSalt
aglex59over 3 years agoLucky guy this Warren. An excellent story....and although i am not fan of stories with tons of chapters, this one needs at least one more. What will happen with the niece spending rest of the summer, will it be His dream girl? Is it going to be a ménage à trois? Please write one more chapter!!!
Subgearover 3 years agoGreat story & stories you have me Cumming alot and started me on eating my own cum Hmmm, U are so seductive and so sweet my trans friends love it
Trecinister1over 3 years agoThis story needs to continue. The niece and aunt having their way with him and eventually the niece and Warren becoming a couple and getting married.
Anonymousalmost 4 years agoLmao that's not how you introduce someone to anal without hurting them... thrusting it in quick with no lube is a good way to scare them off forever.
Anonymousabout 4 years agoA relatively patient Dominatrix that is loving and supportive to her young lover. A wonderful fantasy story, so sweet!
Anonymousover 4 years agoThis was an amazing story I had so much envy for young Warren I wanted to be in his place id give anything to experience this. Please tell me theres more to cump..
Huskyoneover 4 years agoThat was hot, I hope there’s more and he gets to fuck the nieces tight pussy while she fucks her aunts.
Anonymousover 4 years agoThe variation of the niece and Barbara dominating him are mouthwatering. Prequels of her giving and receiving and more in depth with Blake would be good
Anonymousover 4 years agoI would love to see a variation of this story plot, where the big mature shemale moves in next door. Her neighbor, written from the perspective of every horny middle aged man, happens to look over his back fence and discovers her working in the garden next door.
Anonymousover 4 years agoMy girlfriend has a penis and tits. She passes as a female and I love her. She says she keeps me around as I suck her off every morning. She loves to fuck me and makes me beg before I can fuck her. She brings her friends over to duck me and I love it. I can’t tell how much cum I have swallowed. I am her sissy boyfriend.
Westfjordianover 4 years agoThis story always makes me so damn hot. Exactly the kind of domination I love; gentle and assertive. Honestly one of your best.
TerraKhanalmost 5 years agoHow about you write a prequel, stories from her early years when she was a "bitch."
Like when she fucked Blake in the back seat of his '78 Dodge and when she fucked the saleman, those stories would be fucking hot.
Just think about it....
Lenny20about 5 years agoA Part 2 with her niece would be nice. That was a really good story with amazing sex sprinkled everywhere!
RodimusMikeover 5 years agoEven tho Barbara was somewhat dominant with Warren she did it with love to show him not all women found him unattractive,she showed him Tgirls absolutely adored him for his small submissiveness where they could take his ass and mouth and give him all the cum he wanted.
As for Barbara's Niece coming for the summer I kinda wish she would fall in love with Warren and they become a couple and them and Barbara stayed together and shared Warren's wonderful little ass forever,so beautiful.
Anonymousover 5 years agoIt'd be interesting to see the interactions with Barbara's niece and the two of them.
Anonymousover 6 years agoThanks for the story. I loved how you kept me wandering about when things were going to get hot and how you slowly led me into a series of events that just kept taking me deeper and deeper. I felt like I was there and Barbara was seducing me. Awesome job
gmag47over 6 years agoWow that was super super hot wish it was me getting my straight virgin ass fucked and owned!!!
snorkie1979over 7 years agoGreat story,reminds me of one I meet years back.She was so hot and what a cock on her.Spent many hours of us sucking and fucking each other.
Anonymousover 7 years agoThat can't be the end of the story,that is only the beginning....Isure am curious
how it would continue,real curious....mmmmm
Anonymousover 7 years agowhen will you post the next chapter wioth Barbara's niece ?
Anonymousover 7 years agoI got so horny reading your story I had to jack-off while fingering my pussy. Would love to hear how this ends up. Sounds as though his end is going to be up more than down.
PsylentObserverover 7 years agoGreat read! Would love to see more with this story line. Being spit-roasted by Barb and the niece would be super hot!
Anonymousalmost 8 years agoGod I enjoyed this, wish I would have a Barbara or anyone's monster cock inside my tight ass. Loved it. Please, someone Fuck my ass. Ahhhh
Anonymousalmost 8 years agoThat means I'm ok with it. I had precum on my cargo pants and had to change my underwear and my pants. I'm considering wearing panty liners in my own panties. I don't know if I want to be Barbara or the boy. But either way I liked the story. And I am going to read it again. I can't remember his name. Ok. I want to say more but I have something to do. with my nipples while I read it over again because I could go hands free while I read and play with my nipples. Thank you.
Rubachubalmost 8 years agoGreat story. Please add a chapter soon.
Anonymousalmost 8 years agoits been way to long, you should continue this story, i wanna see what happens when her niece cuts to visit!!!! please continue the story
will281over 8 years agoWhile I thoroughly enjoyed the seduction of Warren, I couldn't help but think that I would have preferred my nectar directly from the source. So, I understand why Barbara had to approach him differently, as she probably did other conquests. When a college sophomore, a college professor groomed me by tossing my salad while worshiping my body orally. His tongue working its magic against my virgin rosebud was both thrilling and exciting. It was so intense that I couldn't distinguish it from his meaty nine inch cock as he attempted to deflower me. In a state of euphoria, I didn't know whether it was his tongue or his penis driving into me for several seconds or minutes. Nonetheless, I resisted his invasion when the euphoria subsided and I could focus clearly on what was happening. Secretly, I had fantasized about giving up my anal virginity from my very first homosexual encounter with a high school teacher three years earlier. Unlike Warren, I chickened out from fear. Fear that I would become addicted to it, and fear that he would rip me apart with the monster between his legs. Things may have turned out differently if he had approached me like Barbara did Warren. When Warren entered her life, she was wise and mature -- as was my high school teacher. They both seduced with confident assurance, while creating an atmosphere of comfort and safety.
Anonymousalmost 9 years agoshemale is incredibly offensive. she is a trans woman, not a shemale.
good story tho.
Anonymousalmost 9 years agoI have to say from all your stories this has to be the best 1 in my opinion and as I look down the list of comments quite a lot of people seem to agree. From the first moments in the pool to the actual sex at the end the story is super hot. I Love the way she has him drink the Girlcum out of the Glass and I Loved the Blowjob scene too.
I would Love to read how the rest of Warren's Summer went :P
Please, Please Listen to your Loyal fans and write a sequel to this Story!!!
