Down-low With Sister’s Boyfriend

I pulled down his shorts and his cock popped out like a Jack in the Box toy, springing straight out and pointing at an upwards angle towards my forehead. I was the most fabulous exciting thing I had ever seen.



I’m Danny, me and my sister, Dana, were born 8 minutes apart. Identical twins we looked exactly alike and developed a strong bond from birth. Dana was and will always be my best friend. Except for my parents, and a few other people, most people could not tell us apart until we were about 10 years old.

As we got older, some still struggled with our identities. It was really kind of funny, as we would sometimes pretend to be each other just to confuse people. I would be rich if I had a dollar for every time I heard someone ask my parents, “I can’t tell them apart, who’s who?”

Even as we grew into our teens, whenever we were together, people always remarked that we looked exactly like each other. If I had worn my hair shorter, maybe everyone could tell who was who, but I didn’t. Our parents let us choose our own hair styles and I liked mine long, just like Dana’s but maybe a few inches shorter.

Growing up, Dana was my best friend and to this day, still is. I confided everything to her as she did to me. As a child, I often played games with her and with her female gender toys. She had a dollhouse that we spent hours playing with. Dressing up her dolls and playing make believe was part of my early childhood. I was just a kid then and really didn’t think anything was wrong with it. My parents never really discouraged it either, probably glad that we never fought, they seemed happy that we got along so well and left us to our own devices.

We did everything together, absolutely everything. We were inseparable as kids. Our parents enrolled both of us in swimming and acrobat/tumbling classes when we were nine. We both stayed seriously involved in both classes til we were 14 years old and started high school. We just didn’t have time for it anymore. We both started out short and thin, as me and Dana both took after our mom, both our bodies gradually developed from 5 years of these classes.

We both developed strong firm legs and our upper thighs had become especially thick and toned. We developed very firm muscular lower bodies, but still remained pretty lean overall, we were both in great shape. Neither of us developed a muscular upper body at all, toned but not muscular. Everything else from the waist down, especially our legs, thighs and especially our glutes became larger and firmer. As we grew older, I loved how my body looked, still very much resembling Dana’s. I definitely had her big muscular rounded butt, which I really kind of secretly liked.

When Dana announced she was joining the high school track team, I followed her like I always did. All the running really made my thighs even thicker and firmer, along with my already big ass. It just became rounder, fatter, firmer and more toned.

By the end of high school, I realized I had peaked and this was gonna be my body for the rest of my life. I was 5’7″s tall, same as Dana, and weighed 135 pounds, just 5 pounds heavier than her. I still had my long blonde hair, just like hers, that I usually wore pulled back in a ponytail. I am often still mistaken as a girl, both in person by strangers sometimes and even on the phone. I guess I have a soft voice also to go along with my somewhat effeminate facial features. I’m more pretty than manly.

I think I finally came to realize I was different when I turned 18 years old. I was just not interested in girls. It’s not that girls didn’t pursue me, they did somewhat, I just wasn’t that interested in them. I had my sister’s features and she was very popular. Dana was so pretty I actually envied her, but the girls, I just wasn’t interested in them. Even at 18, people would say we looked so much alike it’s hard to tell us apart from the back.

While my sister dated the same guy, her longtime boyfriend Tony, all through her high school years, my personal sex life finally began after high school. I had my first gay encounter when high school ended with a guy when I was 18.

A friend from the track team stayed over our house that night and it just happened. Sometime in the middle of the night, I felt his hard cock poking into my back. He was aroused and took my hand and placed it on his cock. It was intoxicating to touch his cock. Like a fish to water, I knew what I wanted and went under the covers and sucked his beautiful 6″ circumcised cock passionately until he exploded in my mouth. He never even touched my cock, but my hands free orgasm was simultaneous with his. It was the most exciting moment of my young life as I knew this was my destiny. We continued a clandestine sexual arrangement all that summer til I went off to college. Always with me sucking his cock, which progressed to him taking my ass, which is where I had my first anal orgasm. I knew then I was gay and liked guys way more than girls.

My parents, my sister, and a couple of my close friends all knew I was “different”. It was never spoken about or questioned. I never dated girls, or even guys openly, but loved every chance I got with my summer friend. My family accepted this in me and they never had issues with it. I confided with Dana in intimate details about everything me and my friend did.

Dana had been involved with Anthony for a few years now. They finally tied the knot when she turned 20, still in college. Her marriage and moving out didn’t affect our close relationship at all. We saw each other regularly, and if not, we spoke on the phone several times a day. Even though she was now married, we were still best friends.

Anthony was 2 years older then her and had just graduated college and secured a really good job in an accounting firm. He was a nice guy and he seemed to dote over my sister. I thought Anthony was very attractive. I loved his abs, they were sexy. He went to the gym regularly, played softball on the weekends and was tall and dark. He was about 6′ 2″s tall which dwarfed my sister, but they made a very attractive couple and had lots of friends. I was happy for her and we still maintained a very close relationship even though they purchased a home in our hometown and I was left alone at my parent’s home til I graduated.

Me and Dana both graduated together when we were 22 years old. I was hired fresh out of college with a website design/graphic company and finally flew the coop and got my own apartment. I had met a guy my sophomore year in college, and we had a hot and heavy discreet sexual arrangement where we would hook up in his or my dorm room occasionally.

It was always the same with me and him. He had the most magnificent cock and loved for me to worship it orally. He absolutely loved my big, plump, firm smooth ass and would fuck me senseless as often as possible. I absolutely adored sucking his 7″ cut cock, but my favorite thing was when he got me buns up kneeling and fucked my ass til he exploded.

Anyway, one day out of the blue, Dana called me with great news. “You’re gonna be an uncle Danny.” she screamed into the phone.”

I was so happy for her and Anthony. I was also excited of getting the label “uncle”, it felt like such an honor. In the next few months Dana’s belly began to swell, showing off my expected nephew or niece. Wouldn’t it be funny if she had twins I laughed to myself. Her pregnancy really seemed to slow her down as she struggled with the difference in her body and mood. All her life she had been so active and now she had slowed to a snail’s pace. Almost unhappy at times, she finally confided to me on the phone in her 6th month of pregnancy that she was having a difficult time satisfying Anthony in bed. It was really bothering her as they had a very active sex life.

We had talked about our sex lives candidly in the past, she definitely knew I was gay. I shared stories about sex with guys in graphic detail with her, as she did with me about Anthony. We compared details like best friends do. While she knew in great detail from me telling her stories, that I loved anal sex, she on the other hand had tried it several times unsuccessfully, with tips from me on enjoying it to no avail. Dana always came back to the same thing, Anthony’s cock was too big and it hurt. I told her my first time hurt, but you get used to it and will start to love it. She told me they tried several times before, but again, he was just too big. I finally had to ask he, how big was he.

She told me she had actually measured it before and it was 8 1/2’s long, but that wasn’t the problem. She said the reason it hurt her butt so much was that it was really thick. Actually, “really, really, really thick” is what she said. While I laughed at her last comment, I noticed a tingling in my hardening cock as this was exciting me. She continued explaining her dilemma, and I went silent only half listening as I imagined Anthony’s big cock. I’m a little embarrassed so say that all I could think about while she was talking was what his cock really looked like.

Over the next few weeks, as she got even bigger, sex with Anthony, or lack of sex, seemed to dominate our phone calls. Where she loved vaginal sex before and relished his length and girth, she said it was now very uncomfortable due to her pregnancy. She said she almost hated it when he tried to initiate sex and would always try to satisfy him orally, but even that was an issue.

Dana had never been able to make him cum from just oral in the past and she said it frustrated both of them that she couldn’t. She complained that he kept begging for her to give him deep throat, but it made her gag. As I was accomplished with that with my lovers, I tried to give her tips over the next few days on how to deep throat, but she complained that it made her gag and she actually threw up the last time they tried.

She finally admitted that sex was becoming an issue as she loved Anthony and wanted to please him, but felt guilty as she seemed to fail at it. My poor sister was really upset that she couldn’t satisfy her husband and it really began to weigh on her.

What she said next floored me. “Danny, would you help me please. I’m gonna ask you a favor and I hope you don’t think I’m being too weird, but I don’t know what else to do. I wouldn’t be hurt if you said no, but will you please consider it overnight and let me know tomorrow?”

I was stumped for a second, completely silent, just digesting what she said and hoping she would finally speak again, when she stuttered out the words, “Would you take care of Anthony’s needs for me?”

Oh my God, oh my god, oh my God. I couldn’t believe what I was hearing. I was stunned, almost expecting her to say, “I’m just kidding.” but all that followed was silence.

“Dana are you serious?” was all I could utter.

“Yes Danny, I want to make Anthony happy, but could never agree to him being with another woman. I actually brought this up as a joke the other night after another failed attempt at sex, saying you should have married my brother, he can do all these things. I said it as a joke but he gave me a look that made me think he was actually receptive to that idea. We talked about it some more and both thought it might be a good idea, if I didn’t mind that you helped him out. Would you think about it and let me know tomorrow?”

After another long pause from both of us, I finally said, “Yes, I will think about it, I gotta go now, love you sis.” and hung up the phone.

I knew the answer I wanted to give her right away. Yes I will do it, I would love to, I have actually fantasized about him often, but I didn’t want to seem too eager to agree.

I remembered an incident that happened a few years ago. I was standing in our parent’s kitchen, home alone I thought, gulping down a glass of orange juice, after doing a 10 mile run. I was wearing my tight running shorts, a sweaty t-shirt and tennis shoes when someone grabbed me from behind and pressed into me. I froze until this person kissed my neck then spun around seeing Anthony standing there. We were both shocked as he began apologizing profusely saying he thought I was Dana. We finally laughed it off and went about our day, but I’ll never forget how good he felt holding me, nestling and grinding his pelvis into my bottom.

So, the next morning I called Dana and told her I would do this for her, but lets talk about the boundaries. What did he expect, what would she allow, what would I agree to? I had to find out where this was going.

She told me Anthony always wanted to try anal, but she could never satisfy him on that. She told me he always wanted deep throat, but she wasn’t capable of that either. Could I do these things for him?

I agreed and said I think I could, acknowledging his size may be a problem, but I was pretty sure I could handle it, thinking she had been exaggerating a bit about his size. I knew I wanted to try.

She said that she would like me to fill in for her til 4-8 weeks after her delivery, but maybe not that long if she felt better. I agreed to that too, I wasn’t seeing anyone at the time and was missing a good hard fucking and cock to suck on.

Then she threw me a curve ball.

“Danny, Anthony is not gay, but he wants to do this. He is really hoping we can work something out. He has never been with a guy before sexually and asked if I would ask you, if you wouldn’t mind dressing up a little feminine for him. He also said you have a killer rear end just like mine.” she giggled.

“And, if you could dress the part, it would be a lot easier for him. I know I’m asking a lot, but would that be too much?” she almost begged.

I actually blushed when I heard the “killer rear end” comment. “Ooooh my God, I guess so, I could wear some of your lingerie, but I don’t know how to do make up or any of that stuff.” I excitedly replied.

“Don’t worry sweetie, I will fix you up and then leave you two at the house alone. I can go catch a movie for a few hours to give you some time. Would that work?” she almost begged again.

My cock was now absolutely rock hard listening to her plan. “Sure sis, when do you want to do this?”

“Would tomorrow afternoon be too soon? Maybe come over about 2PM, he will get home around 5ish. I could get you a couple of glasses of wine to get you mellow and I will help dress you up.” she explained.

I wasn’t expecting this to happen so soon, but I quickly agreed and said I would come over tomorrow at 2PM. When I hung up the phone, I realized my cock was rock hard.

That night, I could barely sleep, my cock was hard when I got in bed. My 5 inches poked straight up tenting my underwear thinking about Anthony’s big cock. I finally fell asleep and woke about 3AM from having an erotic wet dream about me dressed as a sexy girl giving my mouth and ass to Anthony.

I arrived at Dana’s at 2PM on the dot. I had given myself several enemas to make sure I was cleaned out. Dana wasted no time in getting to work on me. She led me to the bathroom with instructions to shave what little hair off that I had on my legs. I went a step further and shaved my cock and balls completely and even the few hairs around my ass. I had no hair on my chest, so that wasn’t even an issue. I washed my hair with her shampoo and use her lotion on my body. I felt really sexy as I came out wearing just a towel around my waist.

“Danny, come sit at my vanity in front of the mirror, I want to do your make up for you.” she instructed me.

She must have spent an hour making my face, blow drying my hair and brushing it out. She even parted it in the middle like she wore hers. She then unexpectedly attached some long glue on nails to my fingertips, bright red to match my outfit, they looked so sexy. When I looked in the mirror I was shocked. It was like I was looking at Dana herself. I looked exactly like her.

“Pretty hot huh brother?” she giggled.

“Oh my God, I look just like you.” I replied.

“We’re not done yet, we have to dress you, it’s getting late. I have a pair of red toe to thigh lace stockings, red garters that attach to some red bikini thong underwear, a matching red bra and red lace finger less gloves that will go all the way past your elbows. Put these on and lets see what we got.” she said smiling mischievously at me.

I just froze with embarrassment, not wanting to step out of my towel in front of her, as I now had an intense erection that I didn’t want her to see.

“Come on Danny, he’s gonna be here in less than 30 minutes, get a move on, lets go.” she egged me on.

I turned away from her to hide my erection and fumbled with all these things I didn’t know how to put on. The panties were easy, but they did nothing to conceal my rock hard 5 inches. My cock head peeked out the top waistband. With my back to her, still moving too slowly trying to figure out the stockings and with these long fingernails slowing me down, Dana was becoming exasperated with my slow efforts.

Coming around my front, seeing my erection, she just giggled looking at it and said, “I think you are going to be a bit intimidated when you see Anthony’s cock.”

I blushed deeply as she forced me down into the chair. Kneeling in front of me and beginning to dress me, the stocking came first. The stockings felt so good on my shaved legs, nice and snug. The lacy bra felt strange at first, I didn’t quite fill it out, but as my sister was a B cup, it looked okay, just a little loose. The finger less gloves and garter belts were really sexy and they made the ensemble complete. The last thing she put on was a lacy red silk choker that clasped by velcro in the back. Spinning me around to face the mirror, I was shocked to see myself. I was my sister, a perfect image of her as sexy as I could of ever imagined her.

“How’s that look?” she beamed back at me in the mirror.

My throat was so dry I could barely speak.

She had just spritzed me twice with cologne when we heard the front door open. Dana stuck her head out the door and hollered, “Wait a minute, we’re almost ready, I’ll be right out.”

With that, she lit a candle, turned off the lights and kissed me on the cheek. “Have fun Danny, take care of my husband, I love you for this.” and with that she was gone, closing the door behind her.

I heard a few minutes of talking between them, then the front door closing, assuming that was Dana leaving, while I sat patiently in the almost totally dark room for Anthony.

As Anthony walked in, he stopped dead in his tracks starring at me as I sat quietly on the bed. “Good Lord Danny, I would swear you were Dana, you look beautiful, so fucking sexy.” he beamed. “Stand up, let me look at you.”

“Spin around, let me see your ass.” he almost growled obviously feeling more confident and acclimated to what was about to happen.

As I spun and stopped to face him, he walked up to me and kissed me fully and passionately on and into my mouth. This I never expected and was never discussed. I melted into his arms as his hands went to my butt cheeks and squeezed them.

“God I love that ass. Would you suck my cock for me please?” he almost begged like a little kid.

As he unbuttoned his shirt I fumbled with his belt and zipper. When his trousers hit the floor, I knelt down and lifted one of his feet and removed his shoe and sock, then the other as he kicked his pants away.

With his shirt now off he stood in front of me in only his boxer shorts. I could see the most tremendous bulge of his cock straining the fabric.

Still kneeling I slowly pulled down his shorts and his cock popped out like a Jack in the Box toy, springing straight out and pointing at an upwards angle towards my forehead. I was the most fabulous exciting thing I had ever seen. What Dana claimed she had measured was 8 1/2 inches, I would have sworn it was bigger than that.

So strong, so hard, so masculine it was an unbelievable sight. Big and angry looking with strong veins popping out everywhere. But what really shocked me was his girth. It was so thick it looked almost unreal, and if the shaft wasn’t thick enough, the head of his cock was even thicker than his shaft.

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7 thoughts on “Down-low With Sister’s Boyfriend

  1. Robbie says:

    I am thinking the more they have sex and Danny keeps taking all his dick, he would eventually want to have sex with Danny a lot more then his wife Danny’s twin sister and she can’t get upset with either of them in the future or she better learn to take all that thickness in her all 3 of her holes all the way!

  2. MJF says:

    Body shaved, makeup, fingernails painted, lingerie just so a “str8” guy can use you yet the only thing missing here was the word pussy used 2 reference the guys ass. How did this happen? Otherwise a hot story.

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