Bobby, my favorite uncle, called me late lastnite while i lounged in my bed,enjoying my boyfriends tongue deep in my pussy. He was my favorite uncle of all my big black uncles, sporting thick,smooth muscles & a tasty 11inch black cock & was going crazy thinking about stretching my pussy to its limit with his thick,purple mushroom headed pussy pleaser! He started telling me, "tell ur boyfriend2clean ur pussy good til i get there. I need u2be ready 2ride this cock&give me ur cum. This big black cock is urs. Ima be rite there2fill ur pink hole with my cum...nice&deep....i think ima nut twice just... Continue»
The title of this story isn't really accurate as I wasn't fucking Uncle Bobby see Uncle Bobby was fucking me! He wasn't really my uncle he was just my mother's boyfriend but he lived with us so it was kind of like he was my Dad I really like him a lot he gave me lots of attention and took me places and gave me money for doing chores for him he really was a good guy! He had a boat and it was a nice one too he kept it docked at the Marina and one weekend he asked me if I wanted to go fishing with him well I loved to fish and I loved boats so hell yes was my response and we set out to go fishing that Saturday it was a beautiful day not windy just a few clouds floating around perfect for a day on the water! My name is Trudeau I know it a strange name and boy do the bullies at school love to make fun of it! Like saying hey k** whats your name? True Duh? That really fits you asshole! And they'd all laugh hysterically... I had just turned sixteen and I was built kind of slim I had a long dancers body like my mother I had muscle but it never stood out no matter how I tried my face wasn't bad but it looked rather feminine and my lips were too full needless to say the girls didn't flock to me like some of the other more brawny guys but that's the way it is sometimes...I figured I would come into my own soon enough! Anyway Uncle Bobby always called me Tru and I liked that nickname! We set out early even before Mom was up Mom's a heavy sl**per a bomb could go off and you'd have to shake her awake to tell her about it! Her name is Sheri and she met Bobby at a club she was singing at called The Jade Room Bobby was with some buddies at a table in the front and when their eyes met that was it! Shortly after that Bobby came to live with us... at first I was leery but Bobby quickly won me over he had his own contracting company that was doing very well so he had lots of money which was a plus so the day before we went fishing we went to the sporting goods store and bought me some new fishing gear as he wasn't impressed with the crappy fishing pole I already had! We talked on the way to the shore about my school what I liked to do music that I liked did I have a girlfriend to which I answered no not yet he just laughed and jabbed me in the arm and told me not to worry that before long the girls would be lining up to date a handsome guy like me and like a girl I blushed and just shrugged my shoulders but he said he would coach me a little and that I would be fine! He also told me that I could work with him and make a little money this summer and that made me smile...he said that you have to have some cash in your pocket or you'll never score with the ladies you can't take them out if your broke! I agreed and thanked him for his offer! It was going to be a great day I could tell... We drove to the marina it was called Safe Harbor lots of boats were docked there some big some not so big and we walked down the row until we came to Bobby's boat it was a beautiful thing wide and tall with all the rigging for fishing the motor was an inboard diesel and the name was Dead Man's Hand because he had won the boat in a high stakes poker game with aces and eight's as his winning hand! I was in awe it was so beautiful Bobby said stop gawking or we'll never do any fishing but I think he liked showing off his boat! Then we put all our gear on board along with a big cooler to keep the fish cold that we filled with bags of ice tearing them open and dumping them in!
When everything was stowed Bobby showed me how to start the boat we went inside the cabin and there was a dash board with lots of gauges and a wheel to steer it had a throttle handle to make it go and a nice radio for communicating with other boats or the coast guard I was fascinated there was a key and he told me to turn it to the right and push a button and when I did the big diesel engine rumbled to life then we cast off our mooring lines Bobby guided the boat out of the slip and we motored off into the bay and as we cruised on to the inlet that would take us out into the ocean I thought about how lucky I was that Mom had found such a great guy and that this great guy was taking such an interest in me! We cruised through the inlet and I watched the open sea unfold its splendor before us for it was a relatively calm day and the sea was a beautiful dark blue gentle waves slapped against our hull as we motored out away from the shore line and out into the open ocean then Bobby called me to the controls and even though he wasn't supposed to he let me steer he said he would let me read his book on boat safety and that I could take the course to get my own boat license I was thrilled and as he stood behind me showing me what the different gauges and switches did I felt very safe and very happy this was one of the best days of my life! Bobby knew where he was going and soon we were fishing...I had no idea how to fish for these particular fish Striper's we were using top water lures called poppers and they did just like their name suggests you play them over the water making them pop on the surface that popping makes the Striper attack the lure and after a few casts I hooked a nice fish Bobby put his pole in the rod holder and came up behind me and was giving me pointers on fighting this fish and as he was instructing he unzipped my fly and reached into my shorts and took out my cock! “Nice cock Tru! Just keep the rod up and tire him out this will be fun if you let it be!” He began stroking my cock and it got hard I was excited fighting the fish and now I was excited getting myself masturbated by Bobby he knew how to jerk off all guys do and he slowly stroked me all the while talking to me telling me about the fish and what he was doing below the water after a while he tightened the drag and sais we were bringing this bad boy in and I began cranking in the line and Bobby began cranking on my dick he was going to make me cum but I held it back until the fish broke water the I came and my cock began squirting cum over the side of the boat out into the sea where it floated on the waves when I finished cumming Bobby helped me land the fish as we hauled this monster into the boat I could feel my erection begin to deflate but I was still very excited it was my first Striper and my first sex other than my own hand! We measured and weighed the fish it was 31 pounds and 36 inches Bobby called it a really nice fish and I was practically glowing with pride! After we had stowed the fish inside the big cooler Bobby took me in his arms he looked into my eyes and said “Just because you enjoyed that doesn't mean your gay it means your bisexual like me...You still like girls right?” I nodded and he said “Good being bisexual is the best because you can have sex with a beautiful girl or a cute guy which ever one comes your way and as long as your cool with it everything's great!”
It made sense to me and then Bobby kissed me and I let him and I felt my arms go around him as my lips parted and his tongue slipped into my mouth I could feel myself getting aroused again and by the time he broke the kiss I had another hard on...He took it in his hand and smiled “This has to stay between us though Tru your Mom wouldn't understand!” I said “Okay just between us its our secret!” Then he kissed me again and said “Now its my turn to catch a fish!” It didn't take him long to hook into a big one and I could see the muscles bulge in his arms as he set the hook so I took the opportunity to return the favor and stepped up along side him and unzipped his fly and took out his cock and what a cock it was now I understood the cries of pleasure coming from Mom's bedroom he had to be ten inches long easy and thick too my hand barely fit around it so I got in front of him and took him in both hands stroking him slowly like he did me and as I was doing that I did something I never thought I ever would I took Bobby's cock head into my mouth and sucked it a little...the head was big and took up my whole mouth but I did my best then I got up and got behind him I wanted to see his cum on the water too so I wrapped both hands around Bobby's other pole and began to slowly masturbate him and as he was fighting the fish he would stop to watch me doing him I think he really liked it! As the fish got closer I stroked him harder so he could cum when I needed him too and he did...just as the fish broke water I gave his cock a mighty stroke and cum shot out of him like a fire hose arching over the transom into the splashing water when he was finished I let go and he landed the fish I had to gaff the sucker to get it into the boat and it was a beauty bigger than mine but Bobby didn't make a big deal out of that we just stowed the fish also a Striper in the cooler. Bobby looked at me then kissed me real nice like you'd kiss a woman and said “That was fucking amazing Tru did you like doing it?” I looked down at my hands the still had his cum all over them and licked a big glob off my knuckle swallowed it smiled and said “Yeah that was fun!” I had never tasted anyone's cum other than my own before and I tasted mine just to see what it tasted like! Bobby's tasted better maybe just because it was his I don't know but I liked it so I planned to give him a blow job some time soon bet he'd like that too! After that we just had fun fishing and we caught a couple more fish they weren't Stripers but we had fun anyway. On the way back to our dock Bobby let me drive with him behind me and he pressed himself against me and nuzzled my neck kissing the soft hollows behind my ear I liked that and told him that I liked it and I reached behind me and felt his cock through his shorts and he said “we're going to have lots of fun together but only if you want it okay?” I said “Okay” and we just motored back to port... We cleaned the fish at the dock Bobby showed me how to fillet the Striper to get the most out of it and he said I did a good job of it too! We came home like conquering hero's with fish tales that we regaled to Mom leaving out the sex part of course that was our business and ours alone. We stored the fish fillets in the chest freezer in the basement and then went and shot some hoops in the driveway later when we were all watching some television I began thinking about our day about how much I enjoyed being with Bobby and how I enjoyed him making me cum and returning the favor I had a feeling that Bobby was going to come to me tonight I had a feeling he wanted to fuck me and would come tonight to get his prize! I wanted to have more sex with him too so if he came to me I was going to be ready....I excused myself after a while and went to the bathroom took a shower and made myself smell nice I powdered and put lotion all over my body I wanted to feel soft to him...then I squirted some lotion into my ass for lubrication I had the feeling I was going to need it Bobby was really big and I was a virgin so I had to be prepared! Good thing too because early in the morning I heard my door click open then I heard the lock click and soft foot steps come up to my bed...I was laying there naked under the covers and I threw them back so he could see me then he slid into bed with me taking me in his arms “You knew I was coming didn't you?” he whispered into my ear “I hoped!” I whispered back and he kissed me then with a passion that surprised me my body molded itself to him and my hand went to find his cock which was easy to find as hard and big as it was I stroked it a few times as Bobby kissed me “Turn over Tru put a pillow under your hips and spread your legs a little!” he whispered as he nibbled on my earlobe and I happily complied when I was ready Bobby got on top of me I shivered with anticipation knowing what was coming next I had thought about it and wanted to do it for him to let him have me in the most intimate way I knew the first time would be a little tough as my little virgin asshole has never been breached but all that was about to change! Bobby's huge cock slid between the smooth round cheeks of my ass which were really nice looking firm but full and I had shaved too removing all the hair between my ass crack and as he slipped between my cheeks I groaned into my other pillow I let some lotion escape my ass to help him enter and as his cock lubricated I was ready for him...He kissed the back of my neck then the side as his hands roamed over my body then he said “Guide me in Baby!” and I reached back and took him in my right hand and pointed him to my entrance I let out a little more lotion as he began to press into me and I felt myself stretching open as that cock head burrowed its way inside I moaned with a combination of pain and pleasure that only guys brave enough to do this can appreciate and I wanted to do this! A secret side of me has always been a little gay heck I've even dressed up in Mom's bra, panties and high heels put one of her wigs on; the long blond one added some make up and some lip stick and I had to admit it I looked really hot! With my long legs and slim body I could pass for female easy...then I would take out my cock and masturbate in front of her full length mirror until I ejaculated all over my image sometimes I even tried on her clothes which fit me great! I wondered if Bobby would like to see me in drag hmmm bet he would I bet he would drag me to bed and fuck my brains out!
I would have to try that with him sometime soon....meanwhile Bobby's cock head is stretching me wide and I stuffed my pillow into my mouth to keep from crying out and I just had to get him inside me so I pushed back a little bearing down on my sphincter it popped into me and I groaned into my pillow but the thing about Bobby's cock and I noticed this when I masturbated him today is that he just gets thicker his cock is shaped like a stalagmite getting gradually thicker to the base so I had a lot more stretching to do to get him all inside me! Finally I felt his pubic hair and his big balls between my cheeks he felt like he could bump my tonsils he was so far up inside me and I thought to myself “ So this is what its like to be fucked I had thought about that a few times after seeing gay guys together here and there sometimes at the mall I wondered who was fucking who and did they like it? Now I was going to find out! I knew one thing for sure...I liked it!” Bobby stroked me slowly working it in and out of me and I began to loosen up and the more I did the better it felt soon I was whispering to him to “Fuck me! Fuck me hard!” Bobby did me like this for a little while then slipped out of me and turned me over and slid back into me I wrapped my long legs around the small of his back planting my heels behind his ass cheeks I pushed him deep into me as his lips found mine and our tongues met in my mouth I moaned against his lips and he moaned into mine our hands roamed all over each other bodies and it felt so good! I thought to myself “Now I'm Bobby's girl!” After a few minutes he had us change positions again and I happily complied I was riding him bouncing up and down he was so deep inside me I wanted to moan loudly but I kept quiet we had to be discreet and as I bounced he took my cock in his hand and stroked me to the same beat as our fucking soon he had me cumming and after I did we changed again and I was mounted doggie style I liked it on my hands and knees with his hands gripping my hips he slid that huge stalagmite of a cock back into me with a passion and my ass cheeks were pounded by the assault I even managed to cum again as his cock was driving into me and hitting a sweet spot inside and it gave me another erection so I stroked myself as he fucked me hard riding my young ass like this was the last fuck he would ever have in life! I felt him cum as his cock seemed to swell inside me then his breathing got ragged and with a groan he began filling my ass with sperm thick gobs of it spattered the walls of my colon painting my insides white as I frantically beat my own cock to another orgasm and as my cum hit the headboard I thought to myself “We have to do that again!” then he collapsed on top of me and we lay like that for awhile with his great big stalagmite cock still leaking cum into me... before he went back to my Moms room he kissed me and asked me if I liked it I answered that by taking his cock in my right hand and squeezing his balls with my left then he brushed back the hair from my eyes and softly kissed my bruised lips again then slipped out the door not making a sound...I lay there for awhile just smiling I never knew two guys could feel that much pleasure together I was definitely Bisexual maybe even a little more on the gay side after tonight but that was okay too I realized that I had always felt that way anyway! I slept like a baby and in the morning Mom was so happy that Bobby and me were getting along so well if she only knew just how well she'd have a stroke but that was never going to happen Bobby and me were going to be ultra discreet with what we were doing we didn't want to spoil things because as they were they were perfect Mom was happy she had a great guy with a huge cock that fucked her brains out every chance he got and I was happy I had a guy that was teaching me things who gave me a job and who was also fucking my brains out every chance he got it was perfect! On our next fishing trip I brought my changeover gear in a duffel bag Bobby asked me whats in the bag but I just smiled and said don't ask but you'll like it! He smiled and said okay and left it at that so after we got out on the water I excused myself and went down into the cabin and when I emerged a little while later Bobby was astounded I thought I looked pretty hot too between the make up the long blond wig and the sexy bikini I was wearing I looked like a sexy young girl and Bobby liked it too and took me in his arms and kissed me but good fortunately I had taken the no smear lipstick so there was no problem we never even got to fish much but made sure we caught a couple at the end just for show so Mom would think we had fun fishing and we did no question about that! My best memory of that day is myself bent slightly over at the transom while Bobby fucked me from behind he didn't even take off my bikini bottoms just moved them to the side and I thought to myself that if another boat saw us they would think some guy was banging his girlfriend and I liked that thought because at that moment I felt like his girlfriend and I liked the feeling who knew that it could feel so liberating being in drag but it was! I was Trudy that day and in the future when I went drag that's what I called myself and it felt nice to be treated like a lady! Anyway getting back to getting fucked it was beautiful looking out over the water the rolling waves just made our fucking more fun and his cock felt wonderful inside me I moaned and cried out his name begging him to fuck me harder until he finally came shooting cum rockets up my sweet little ass we were careful not to get any cum on Moms bikini and I stuffed a piece of paper towel between my cheeks after...I gave him a blow job later testing out the no smear lipstick and it worked like a charm as he sat in the fish fighting chair with me sucking his big cock one that had already been up my ass but I didn't care not at all I was having the time of my life and maybe even falling in love with Bobby a little but then how could I not? His cum tasted nice when he shot off in my mouth and I showed him a mouthful of cum before I swallowed it! It felt kind of pudding like sliding down my throat and I smiled as I milked the last few drops from his cock licking them off with a swipe of my tongue then I let him hold me in the chair and he looked into my eyes and kissed me telling me that he loved me and that it was okay to love him too but that this is all we would ever have because he intended to marry my Mom!
I was thrilled that they would be getting married as Mom loved him and that meant that he would always be around for me too. I told him that I was happy for them because he wasn't only marring my Mom he was marrying me too I pictured myself in a wedding dress all dolled up and looking hot walking down the isle next to Mom with Bobby waiting for us at the altar all of us reciting vows and then Bobby kissing both of us after we said I do... I giggled to myself at the thought and Bobby said “Whats funny baby?” I shook my head and said “Nothing just me being silly I'm so happy for you guys I am really!” and I kissed him a nice kiss with just a little tongue and we stayed like that for a while with his arms around me...A dolphin jumped out of the water not far from the boat and we both exclaimed how beautiful that was! I thought to myself how wonderful this was being with Bobby especially out here it felt like he was mine and in a way he was...On the way back I took off my wig and makeup and became Tru again but I found that I really like being in drag I liked feeling sexy and feminine and I liked being taken sexually like a woman I was going to have some fun in the future being Trudy yeah this was just the beginning of a new and interesting life for me! I became Trudy again that night and we had a wild time in bed together I had set up the mirror in my room and had lit a small candle so I could see myself being made love to and it was such a turn on I came without touching myself it was a revelation for me this was who I am! I was glowing inside with the knowledge that I could be happy as Trudy and maybe someday I would become her permanently just the thought made me smile. Bobby and Mom were married that spring and it was a beautiful wedding...I was the ring bearer and stood on the altar with them but when it came time to say their vows I said my own and it was as if I was marrying Bobby and when I heard you may now kiss the bride I almost jumped into his arms... oh boy what a disaster that would have been but I restrained myself and beamed a huge smile quietly on the side I was really happy for Mom and really happy for me too as now he was officially ours! I would never call him daddy that would have been too weird and he didn't want me to. He was my Bobby and that's the way he stayed and I loved him with all my heart! We had our own ceremony about three months later we planned a camping trip and of course Mom didn't want to go too many bugs in the woods anyway we never went to the woods we went to another state and a friend of Bobby's married us in a beautiful hotel room I was wearing my mothers wedding dress and I looked beautiful Bobby even said how wonderful I looked we went through the ceremony just like a real one and when we kissed at the end it was amazing!
We spent most of that trip in bed but we did go out to dinner one evening and I got some really interested looks from more than a couple of guys it was really fun being Trudy and I practiced the mannerisms of other women all the little things they do I was becoming and I was enjoying my journey. That was one amazing summer when I left for college the following year it was hard to leave Bobby I was going to miss him terribly Mom was in tears her little boy going off on his own but this was a good thing I needed to get away and leave those two alone together I knew my being there was a distraction and I wanted Mom to be happy so off to college I went my scholarship paid for most of the tuition Bobby and Mom paid the rest but it was there that I learned how to make some money on my own one night I was in a club it was a juice bar no alcohol but that was fine I was in full drag just sitting at my little table sipping my fake margarita when she walked up to me I didn't notice at first I was distracted by a cute guy at the bar when I felt someone near me I looked up and there was this gorgeous young thing smoking hot she was olive skinned with the most amazing green eyes “Is this seat taken?” she asked while already taking the seat “Its all yours!” I managed to stammer out she had taken me by surprise but I think that had been her intention! She sat down and extended her hand “I'm Shyla” she said in the most incredibly sexy and sultry voice “I'm Trudy” but my friends call me Tru I said taking her lovely hand and our eyes met and I could feel the sparks flying “My friends call me Shy though I am anything but!” she giggled and I fell in love...”So what brings you here cruising for hot guys?” I smiled “Maybe!” I said not really meaning it I was terrified that if some guy found out I was a guy too he beat me senseless but I wasn't going to tell her that. She panned the room with her eyes and miffed “Nothing here worth looking at darling good thing we found each other!” She said while touching my arm suggestively “I don't live too far from here would you like to come and see my place I just redecorated and I'd like your opinion!” I thought what the heck maybe I'll get some decorating ideas for when I get my own place so I smiled and said “Sure sounds like fun lets go!” Shyla hooked her arm in mine and e****ted me across the room and out the door I could feel more than a few pairs of eyes following us and I liked the attention I even put a little extra swing into my hips to make my ass more appealing...Shyla on the other hand didn't have to do anything to enhance her sexuality she felt like a sexual dynamo I could feel her energy coming off her in waves and as we made our way down the street to her place we chatted a bit or at least Shyla chatted at me telling me things about the neighborhood what to watch out for where there was good restaurants to dine at and I listened enraptured by her lilting voice making comments whenever I could which wasn't often but that was okay with me! We arrived at her place which was a cute Spanish style home with a terracotta tile roof and plants hanging all around I fell in love with the place a cobblestone walkway led us to a veranda then the front door we entered and I almost gasped the place was so beautiful the living room had stucco and stone walls with a huge fireplace dominating the room also stone the furniture and art complimented the house perfectly and I told her so she beamed with pride and happily began giving me a tour of the house I could see her personal touches in every room we entered the kitchen and it was a cooks paradise with pots and pans hanging from a copper rack mounted to the ceiling I was looking up when suddenly she was up against me I was backed up against the counter but then she knew that her eyes were looking deep into mine and they were the most beautiful eyes I had ever seen sea green with gold and violet flecks inside and I thought to myself if Shyla is into a little girl on girl shes going to be very disappointed! Then she moved closer and her hips met mine and my penis which was becoming aroused was met by another penis and as my eyes widened with the knowledge she smiled and I said “I like what you've done with the place!” She said “Thanks its all me!” then she caressed my cock through my dress with her lovely hand and said “And this is all you! I know what you are I knew the minute I saw you it takes one to know one Trudy...So would you like to have sex with me I haven't showed you the bedroom yet!” Of course I did she was the sexiest thing I had ever seen! I just nodded my head and then she kissed me while reaching under my dress and taking out my cock she took hold of it and led me off to the bedroom which was huge with a four poster bed in the center as beautiful if not more than the rest of the house and as she began to undress me still kissing and touching me while she was doing it my hands got a little busy themselves and I squeezed her luscious pair of tits and found that they were very real! We helped each other out of our dresses then I unhooked her sexy little number of a bra and these two perfect pair of breasts were revealed her nipples were large and succulent sticking out just begging to be sucked so I did and she gasped with pleasure as I took a nipple between my teeth then I kissed my way down her beautifully toned body admiring her belly button stud with the hanging diamond chain so pretty it looked I would just have to get me one of those! I continued on down but then I was being poked under the chin as her cock was at full attention and I got on me knees to admire it and it was perfect just like the rest of her long and thick with a slightly lighter colored head she had a foreskin I had never seen an uncircumcised cock before and I liked the way it looked very natural I licked it from the base to the tip then sucked on the head a little she moaned then pulled away “Not yet baby lets have some other fun first!” Her bed was huge and must have cost a fortune I thought as she pulled me down with her and we lay there side by side just stroking each other kissing and tasting then Shyla looked me in the eye and said “House rules I go first!” and she got on her stomach and raised her perfectly rounded ass up I had never done this before Bobby had always done me but never I him but I was game and so ready my cock was pulsing rock hard so I got behind her and kissed the globes of her ass and she liked that she was glistening a little by her rosebud and I knew she had lubed herself up in anticipation of sex I did that too with Bobby...I got on top of her and kissed her between her shoulder blades she giggled and raised her ass to meet me and I began to enter her I did it slowly as I didn't want to hurt her but she wanted me inside and pushed back so that I slid into her it felt wonderful she groaned with pleasure and pushed back and my cock slid all the way inside her sweet ass was pressed against my groin and I reveled in the feel of it I pushed myself as deep as it would go into her which got a moan of approval from Shyla I began to fuck her slowly pulling it almost all the way out then sliding it back in until her bottom bounced off my groin after a few more strokes she said “Turn me over baby!” and I happily complied I melted into her open arms and our lips met then she took my cock in hand and guided me back to her I slid back inside her and I could feel her cock pressing against my belly it was so long it went well past my navel and I thought about how it would feel inside me now that was going to be fun...I hoped I was next but it didn't matter right now because right now I was making love to this incredibly beautiful creature her black ringlets of hair cascaded over the pillow and her eyes were a sea that I wanted to sail on forever my lips found hers again and our tongues met I caressed her perfect breasts pinching her erect nipples hard so that she arched her back and moaned again...
I was going to cum soon but she wasn't done with me yet she knew tricks to keep me from cumming too soon she reached between us and pinched the base of my cock hard and the feeling of cumming went away she smiled and kissed me then she made me lay on my back and straddled me taking my cock deep inside her ass she bounced up and down what an incredible sight that was her hair was flying all around those perfect tits were moving up and down and her long cock was waving like an orchestra conductors baton it was the most amazing sight I had ever seen! I reached up and felt her magnificent breasts tweaking the nipples like she likes and she threw her head back and cried out then just as I began to feel my cum starting she got off me then she got on her hands and knees and told me to finish this way and to cum all over her back and ass no problem I thought I was a great shooter my cum flies far I always have to be careful when I masturbate otherwise I wind up cleaning my cum off the walls or wherever else it flies! I mounted her from behind it was then I noticed mirrors strategically placed around the bedroom I could see myself fucking her and what a sight that was...my long blond wig cascaded down my shoulders and my bra looked really nice on me and I grabbed her beautiful ass made even more beautiful by this position I could see her balls hanging down and I reached between her cheeks and gave them a gentle squeeze she liked that and moved her ass higher I drove my throbbing cock deep into her juicy ass and my hips slapped into her ass cheeks she moaned loudly begging me to fuck her to fuck her hard and I did! I rode her like the stallion she was driving hard hearing the slap slap of her cheeks I watched myself in the mirror and it helped me hold off my orgasm for as long as I could but then I was over the edge and cumming I pulled out of her ass and let go and the first stream flew so far it hit the headboard and ran down the second stream trailed down her back then I painted her ass with the remaining cum shots shooting a couple directly into her gaping asshole it was the most earth shattering orgasm of my life one I knew I would never forget! She collapsed on the bed but not before reaching back and taking some cum off her ass with her fingers and tasting it and the sight of her doing that looked so hot I almost came again! She had me rub the cum into her skin like a lotion she said she liked the way it tightened her skin and when I was finished it was my turn to get fucked...Shyla took over completely first she had me suck her cock a little more not that it needed any encouraging as it was throbbing hard then she threw me on the bed and with handcuffs that had been hidden near the bedposts I was shackled face down with my ass sticking up Shyla had complete control over me I raised my ass up in anticipation of her cock but I got a surprise when a riding crop came whistling through the air and landed across my buttocks I cried out and pulled against my handcuffs but I wasn't going anywhere! I knew it was a riding crop because I could see her wielding it in the mirror I had never even been spanked before so this was very new to me the funny thing was I kind of liked it...then Shyla said “You've been a bad girl and you need to be punished confess your sins bad girl!” I hesitated not knowing what to say and she brought that crop across my ass again but harder this time I cried out and thought of something I told her about Uncle Bobby about how he seduced me on the boat and how I went along with it and how I liked it even...then about how I liked to dress up like a woman and how I would dress up for Bobby then finally told her about stealing my mothers wedding dress so Bobby could fake marry me in it! I felt better letting all that out I had felt more than a little guilty about that not that I regret doing it but I shouldn't have and I knew it!
Shyla gasped “You have been a naughty girl and you need to be punished! Raise your ass up higher bitch and take your medicine!”. I raised my ass as high as I could and welcomed the lashes that followed as they seemed to cleanse me of those sins...”I'm going to beat you then I'm going to fuck you and you will like it a dirty slut like you needs to be beaten and fucked!” I felt the blows raining across my reddening ass and cried out for mercy but Shyla would have none of it when she felt I had received enough punishment she stopped “Look at that pretty red little ass! Now I'm going to fuck it so get ready bitch this is going to hurt!” I spread my legs a little for her and she grabbed my hips with her beautiful hands and drove her big cock deep into my ass! I cried out in pain but also moaned with pleasure my ass was sore from getting cropped and I could feel every thing she did more her fingers grabbing my ass her hips slamming into my ass with each stroke I kept watching her in the mirror she looked so beautiful and incredibly hot she also looked like she was having fun! The look on her face was one of pure lust and she threw her hair back and grinned into the mirror she saw me watching her from “You like this BITCH tell me you like it! Say it NOW!” I cried out that I liked it and begged her to fuck me hard! She pulled back and placed two well timed slaps across the cheeks of my tender ass eliciting moans of pain and pleasure from me my ass was hers and she used it like it was she fucked me silly and when she came she blasted it all over the cheeks of my red striped ass then she rubbed her cum like a soothing lotion into my skin and it felt good my asshole must have been gaped pretty good as I could feel it breathing when she finished with her lotion I thought she would unlock me from my cuffs but she wasn't done with me yet I felt her playing with my asshole slipping a couple of fingers inside me but then she got bolder and she began to insert her entire hand into my never been fisted ass I cried out as first her knuckles passed into me then her thumb she used her hand like a cock fucking my asshole slowly I was straining against my bonds and moaning “Shut up BITCH you need this! You WANT this! SAY IT! SAT IT NOW!” I told her what she wanted to hear and she finished inserting her hand into my ass! It was incredible to feel her inside me I was so stretched out it was unbelievable that goodness her hands were girly then she made a fist inside me and drew it backwards until my asshole was stretched wide around it she rotated her wrist and I felt her knuckles circling my anus then she pulled it all the way out and punched it back inside me over and over her fist punch fucked my ass until I almost passed out I fell forwards collapsing onto her pillows she lay on top of me kissing my back and the sides of my neck then she unlocked the cuffs turned me over and held me we lay there like that for awhile not talking just touching “You were amazing!” she said kissing me then she asked me a funny question “Would you like to see that again?” “See what again?” I asked Then she reached over to the nightstand and took out a remote she hit a button and a huge painting on the wall changed into a television screen there were nine different frames and when she hit another button we were in all the frames from different angles having sex then she explained that this was how she made money she makes her own sex movies and sells or rents them on the web on her own website called “Sex with Shyla” she showed me the site and it was amazing for it was filled with movies of her having sex with a variety of different men,women and other tranny's … wow I was astounded and aroused as well she asked me if she could use our tape for her site she said she would share the profits with me I said sure and even helped her edit our movie it was fun creating it there were all kinds of zoom in features for close ups and everything! We got along so great together I wound up eventually moving into Shyla's place giving up my dorm room I had a ball living at Shyla's we made many more movies together in some I was even myself my studies came first though she made sure of that!
I took her home to meet my Mom and Mom loved her they chatted like old friends all evening shes happy that I found someone special if she only knew just how special Shyla was she'd snap her twig! Bobby liked her as well and later when I told him about Shyla his eyes lit up so I arranged for Bobby to make a movie with us Shyla got him in the cuffs and fucked him in the ass but good and twards the end he really liked it! We named that one “FUCKING UNCLE BOBBY” bet you could have guessed that one huh...I made sure he fucked Shyla good too I had told her about his stalagmite shaped cock and she was anxious to experience it and while she was I even mouth fucked her from the front while Bobby doggie styled her what a great movie that turned out to be! After I graduated college I went to became a social worker I enjoyed helping people and if the money wasn't all that great we still had plenty from our movies and investments! Mom keeps asking when we're getting married who knows maybe we will eventually I certainly do love her guess we'll just have to see.....Hope you enjoyed my story I had fun telling it!