My Wife's BGFF
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Let me start by saying that my name is Ken, I am about 5ft7in and about 135lbs. with short brownish red hair and hazel eyes. I am married to Janet who is also about 5ft6in and around 125. Like many have guessed, I like to cross dress and Janet while not exactly OK with the dressing, does not complain about my wearing VS thong panties 24/7 and occasionally when we go out, slipping into a pair of her jeans as she says it does make my butt look good and she loves the way my booty swings when I wear her jeans. She does admit to having had a lesbian affair in college and maybe being a bit bisexual and that seems to be the attraction with the skinny nerdy guy she married.....that , and I make her laugh she states on numerous occasions.
The adventure all really started about 6 months ago when we went out and I was in a pair of her jeans, with a nice silk button shirt and she dabbed a small amount of light pink lipstick on me after we kissed and stated that she was getting turned on by thinking of me as her girl friend tonight and that when we got home, I needed to suck her pussy while still wearing the jeans and shirt. Well needless to say, I made it an early night at dinner and got her home and dived into her sweet snatch with me being fully clothed and her naked on the couch holding me against her and shouting when she came multiple times. The next morning I asked her what had her so excited and she stated it must have been the jeans and shirt reminded her of her old girlfriend and made her want that experience again. I told her we could do it again as I loved the way she was so hot and responsive! 2 weeks later when I got home on Friday from my accounting job, she had tight feminine jeans, a silk ladies blouse and one of my camisoles, thigh highs and some red heels I had laid out for me "for our date tonight" and told me to get dressed as best I could so she could see me in femme. Well suffice to say, that with the short hair and all I still looked like a guy in women's clothes even with my sad attempt at makeup. Janet said it would not do and quickly pierced my ears with a needle and ice cube, put on a pair of her big 3inch gold hoops, redid my makeup while she thinned my eyebrows into a Brooke Shields look and then did a quick restyle of my hair into a more Hally Barry look. The results were striking and while I knew I was not a 'hot babe', I could pass under a casual inspection I thought. Janet dressed in skirt and camisole with low heels and took us to a bar across town called the Transporter....A place that catered to alternative lifestyle relationships...and I had no issues when we went in. We ate some pub style food, drank, danced and truly enjoyed ourselves with much hugging, kissing and touching like a new couple would do and it had me really straining in my panties and tight jeans to a point where Janet whispered we would have to get a gaff if we were to keep up this fun dating life. She then said, "If I have anything to say about it, we will be doing this again Kandi baby!" Well when we got home, she was all over me and we made it to the couch where she hiked up her skirt and I noted she was wearing no panties and just dripping wet! I went down on her and she grabbed the back of my head and held me against her till she came with a scream. I dropped my jeans, released my aching cock and slid into her balls deep and started to pump my 5-6 inch manhood in and out until I heard her moan in orgasm again which sent me over the edge and squirted my seed into her with a groan. She got the most angry look I had ever seen on her and she pushed me off, threw me on my back and then squatted onto my face and said " Bitch! I did not say you could come in me like that! Now I want you to clean my snatch with that tongue and never fucking come in me again unless I say so! Is that understood my little sissy slut?" I mumbled an affirmative as best I could with her pussy smashed against my mouth and cleaned her out to another orgasm as she rode my mouth saying "what a good pussy licking slut I was", "how much she loved the way I ate her and drank down my own come". I was shocked at the aggressiveness of her behavior and submissively did as she wanted. When she came again and squirted the last of my love juices and now her own into my mouth, she rolled off me and lay next to me kissing me and telling me how much she loved me, how sexy I was as Kandi and that it just made her so excited to take charge and force herself on me like that! I told her I did not mind as the sex had been better than anything before and if it made her orgasm like that, I was all for it. It made me feel special to please her and give her good orgasms like that! We continued to dress me up en femme on weekends and got me some softball sized and looking stuffed dog toys I could use to pad my bra for a bigger chest as Janet stated she wanted to make me more feminine one night and that weekend we woke up Saturday morning and she had me dress in Jeans, a button blouse with one of my bra and panty sets in light purple with little ankle lace socks and some pink and purple sneakers since we were shopping at the mall and I needed more clothes to keep up this 'game' she was really getting into. We hit the stores and got my own jeans, slacks, tops, nighties, skirts, dresses, VS lingerie and stopped at the shoe store where I saw a pair of red Dorsay heels I had to have! The clerk seemed to flirt with us and when I asked to try the heels on he assisted and played with my feet and commented about how pretty it was to see a lady wearing an anklet these days, and the little heart charm was a nice touch. I decided to wear the heels out as it was now lunch time and I loved the little clip, sound of the heel as I walked. It made me feel truly girly and put a bit of extra swing in my hips I am sure! Janet said she liked the way that clerk was flirting with me and how I was so girly for him and that it turned her on having me as a husband and girl friend to shop with. We ate lunch at the food court and went home to get ready for the trip to Transporter later that night. I shaved and did my legs and then rubbed lotion and powder all over and then put on a red Bra and Panty set with garters and some smoky stockings with the French heal and seams, a little black dress we got this morning and the Red Dorsays again. Fixed up the hair and make up with some long dangly earrings and bracelets. Janet wore a short black pencil skirt and white blouse with no bra and nude fishnets with black heels. I loved the way you could just see her Areola and nipples through the white of the blouse and called her a total tease. We again danced, ate and flirted with each other as two lesbian lovers and when we got home, it was more passionate kissing, caresses and finally me eating her and then sliding a finger into her pussy and her ass and moving them in and out while sucking on her clit until she came. And when I say she came hard, she squirted her juices all over my face and loudly moaned out "Kandi" in a long drawn out explicative. It was great and made me squirt into my panties in a mutual orgasm. She grabbed the back of my head and pushed my mouth onto her and told me to clean her up which I gladly did. When she noted my cream in my panties she licked it up and then fed it to me, saying "you are the one who needs to learn to appreciate this and I am feeding you your spunk from now on my little sissy slut girlfriend!" At that point we both fell asleep and woke refreshed the next morning. I put on a short little robe and went out to make coffee and breakfast while she dozed. Just as I was putting her cup and plate down, she came out from the bedroom in a black Bra and Panty and said I was so good last night, that I deserved a reward and she pushed me up against the cabinet and dropped to her knees, opened my robe and pulled my panties aside and started to suck me off. Looking down at my fake breasts and her bobbing on my cock made me hot and I came quickly. She sucked me a little more to get the last drops and then stood and kissed me. She shocked me by feeding me my come in a wet tongue kiss and then said " I told you, you would be eating your come now Kandi dear, not sure why you are surprised by that?" Today I want to set you up with an appointment to get laser hair removal and a nice long haired wig so I have more hair to hold onto when you blow me! We went downtown and got me a wig and started my full body laser hair removal treatments but she decided I could keep a small thin straight patch over my enlarged clit so it would look sexy later. So a few weeks later a couple packages show up at the house and Janet says these are for this weekend and I do not get to see them till then. With the week almost over, I am can't wait for Friday! The one package ends up being a pair of Mastectomies and some Spirit gum adhesive for me to wear and the second is a large 'T' shaped dildo with one part of the 'T' being the balls and the other a bulb for insertion into Janet so she has a strapless strap on for our fun! I look at it and say, "but honey, it's kind of large isn't it?" She responds with "It's only 10 inches bitch! You need to learn what it is like to be fucked and I know you will love me fucking your little ass pussy with this tonight!" So we dress with her in Jeans and a top and I can tell by the bulge she is wearing that monster cock. I dress with pale blue bra and panty set, suntan pantyhose, the new mastectomies and a little white leather miniskirt, Blue silk top with bell sleeves and some blue pumps. The top is left open to show off the cleavage a bit. My new auburn wig, evening make up, pink glossy lips and jewelry with a little black chocker and Janet says I look like a hot babe now! It is the usual light dinner and a glass or two of wine and when we dance I can feel that bulge pressing against me and Janet is grabbing my ass and saying how she can't wait to fuck me tonight, I look so hot and she loves the idea of taking my virginity tonight. When we get home, I can't believe it, but with all the wine, kissing and that phallus pressing against me and her dirty talk, I am excited and after she drops her pants , she tells me "Suck my cock you sissy bitch! I want you to get it nice and ready for your pussy!" I can't seem to help myself when she gets all authoritative like that and drop to my knees and start to suck that cock. "Yeahh that's right my little slut, you like sucking cock don't' you?" "You want me to fuck you with this cock and make you a real woman ?" She holds my head against the cock so I am forced to deep throat it and says " yeah I thought so. You need cock just like any little slut does, bitch, and I am going to give it to you!" With that she pulls me off her phallus and bends me over the coach and pulls my thong panty aside, spits on my rosebud and tells me "relax, and it will go in easier and then you will like it I am sure!" She pushes it in and I gasp at the pressure, pain and fullness. She holds it there for a few moments and then starts to slide it in and out fucking me good. After just a few minutes I can't help it and start to push back, and she grabs my hair and says "I knew you would like getting fucked you sissy bitch! You are my little slut and I am going to fuck you now whenever I want!" With that I can feel her tense and it sends me over the edge squirting into my panty and moaning how much I love her! "Yeah I knew you liked getting fucked baby, that's why I did this. Now clean me off and your panties as well since I know you fucking came you tramp!" I turn around and slowly lick her phallus clean and then scoop up my come, rub it on her phallus and then clean it again. We then head to bed with thoughts of where this is going in my head and dreams. Now just over 2 months into this game, I am hairless below the nose except for my little patch of pubic, always wearing at least 3 pieces of female clothing at work ( panties, stockings and usually women's slacks ) and totally the submissive slut Janet wants me to be on the weekends! The office gang is noting the dress now and the feminine mannerism I am sure but no one is saying anything to me. Some of the ladies are more friendly while guys are a bit more stand offish, but it is just work so I am not too worried. Now at 3 months in, I am still dressing evenings when I get home and all weekend and our sex life is wonderful! We spend time as Best Girl Friends and lovers with Janet in total control now of our life and all assets. She even sent me out one weekend to get my bellybutton pierced and a little lower back tattoo and then she added a tiny little heart off to the side of my panty line with her initials in it! I have to admit that the humiliations, and her taking charge are totally exciting and when I do enter her during sex and shoot, she always sits on my face and forces me to eat her and swallow our mixed come. I love being her sissy slut girl friend and having her in charge! I have also noted that if I put my finger in her ass, she comes harder and seems to squirt her come straight into my mouth and I am becoming addicted to her squirting orgasms!
One night while we are at Transporters I note 2 tall black gentlemen are talking at the bar and drinking beers as I had not seen them here before and after we get a booth, the waitress drops off 2 glasses of wine as compliments from the gentlemen and we toast them. They ask to join us at the booth and state their names are George and John and that they are new in town starting to work with the Lawyer firm downtown. They are both 'bi' and hope that it is OK if they spend some time getting to know the locals and maybe learn more about the town. So we order food, more wine, and I end up dancing with John while Janet dances with George. Once during a slow dance I can feel Johns manhood start to rise and when I look at him, he just says, "yep, it's really that big! You like black men Kandi or are you strictly gay?" I can't help but to press against him and tease him and ask him "Well do you mind dressers and messing with a married couple? But I have to admit, that snake in your pants feels quite enticing and I do like the idea of sucking on that big black cock you are rubbing against me!" I note at this time that Janet is glued to George and kissing him with plenty of tongue during their slow dance, so when the song ends, I take her into the bathroom to 'powder our noses' and ask her what she is doing with George? "You're kidding me right? I am teasing that guy and enjoying the feel of his huge cock pressing into me and thinking we need to take them home and get fucked by these guys since it has been forever since I had a cock like that in my pussy and let me tell you right now my little sissy bitch....you are going to fuck John tonight while I do George and I do not want to hear another word about it! You will keep him busy while I enjoy a real man fucking me tonight. His cock is huge and I am betting John is just as gifted so enjoy it before I decide to make you watch me fuck them both as I think I could take them both on right now I am so horny! Also the idea of you being fucked by a man has me so hot, I can't stand it" Well shortly after that we end up leaving with the guys driving both cars and I can see at a stop light that Janet has George under her control by wanking him while they drive and I know John sees it and says " I know you are a guy dressed, and Janet is your controlling wife, but you're so damn hot I can't stand it Kandi baby. When we get to your place I am going to treat you like the sissy slut whiteboi I know you are and I have a feeling you will love my big dick." Now I know this was a set up and I still can't help myself when he sounds so authoritative to go all submissive on him and say "Yes John, whatever you want. Can I start by sucking on it as it is way bigger than anything I have seen before?" "Bitch, you are going to suck this big black cock and then I am going to fuck your tight little boy pussy till you can't stand it and beg me for more!"
When we get home, Janet takes George to our room and says "you can stay out here or take John to the guest room. I don't care and we will see you in the morning!" When John calls me over to him on the couch, we start to kiss and his hands are all over me and I can't help but to put my hand on his manhood and gasp at the size and stroke it in his pants. He pulls my hand away from his cock and directs it to his belt buckle. I take the hint and undo his pants and fish out his thick black cock and when I see the precome dripping off it, I just go all girly sissy slut and moan at how big and strong it looks and lick the precome from the tip and start to lick up and down the shaft so it is somewhat lubricated and then take the head into my mouth, licking the head and eye with my tongue and putting my hand around the base and still have a considerable length between the head and my hand! I start to slide it in and out of my mouth concentrating on the head and top part of the shaft. As I get used to the girth, I am able to take more and more into my mouth and know I am at least 2/3rd the way down his manhood and can now feel his hand on the back of my head and moving the hair away from my face and his manhood. I switch from alongside him to on my knees in front of him and with on last desperate 'bob' I can force the rest of him down my throat and hold it while I swallow a few times and then pop off to catch my breath and start sucking on the head and tasting his manhood again and then down the shaft I go. Rinse, repeat and I am slobbering all over his cock and making hungry noises and looking up at him and truly feeling girly and loving the taste of this man's cock in my mouth and starting to wonder if I can truly take him in my ass as I know he will want. After a short while, he stops me and says "Baby, you are one talented cocksucker that is for sure, but I need to pound that sweet sexy little whiteboi ass of yours so drop those panties and climb aboard!" I do as he says and pull down my thong panty and climb onto his lap like a cowgirl and after rubbing his manhood against my rosebud, I sit down on it forcing it into me. It hurts at first due to the size, but as it slides past the sphincter and loosens up a bit, it really starts to feel good, full, hot and alive and I am soon bouncing on it with my arms around his neck, kissing him and telling him "how good his cock feels in my pussy and I can't wait to feel him come inside me!" I feel his hands cup my ass cheeks and help bounce me up and down on that long massive black cock until I feel him get really hard, hot and start spurting inside me which triggers my own orgasm. I ride him till he is soft and pops out of me and then I slide down and clean my spunk from his belly and then our mixed juices from his cock. That's when I can hear Janet's moans and the rhythmic noise of a good sexual bought going on upstairs and ask John if he wants to sleep down here or if I can lead him to the bedroom? He chooses bedroom and when we get in, I strip off the rest of my clothes as he does and we fall asleep in each other's arms to the gentle sound of rhythmic fucking across the way from George and Janet.
In the morning I wake and can feel his arm over my shoulder cupping my 'breast' and his manhood between my cheeks and can't help but to wiggle my butt and angle it so he slides in and starts to fuck my from behind while I twist so we can kiss until he comes again and I squirt all over my stomach. A quick tongue bath and I am putting on panties and a short robe to go make coffee and breakfast for everyone. Shortly after that John cones down and when I give him his coffee, he pulls me into his lap and kisses me and tells me how much he enjoyed last night and this morning and hopes he can call on me again? George and Janet come down both wearing nothing more than a smile and I can see he is indeed as well endowed as John and after breakfast we all end up spending the day sightseeing and enjoying each other's company. We end up seeing John and George every 2 or 3 weeks for about 3 months and we get together for Halloween ( as nurses and doctors ) and at the Law Firms Christmas party as their dates with Janet in a long low cut white evening gown, and strappy heels and no undergarments showing off her wonderful cleavage, while I wear a short tight corseted black mini dress that stops about mid mid thigh with lacy shoulders and long lace sleeves, a red bra and panty set with thigh high stockings and red pumps. My eyes are smoky and lips dark with long red nails instead of my usual French tips and a sexy little ruby necklace chocker with ruby and diamond drop earrings I got from John! We eat, drink, dance and generally have fun till we retire and spend the night lovemaking.
Janet is more and more controlling when we are not around them and even John and George treat me like their slave when not in public, to a point that I am becoming even more submissive and lose my job due to my "erratic behavior and attendance". I break down sobbing in Janet's arms when we both get home and she tells me its OK, She is making good money at the marketing firm, I can find another job and maybe get it as Kandi so I can dress full time! In the mean time, I can be her little house maid till then as she knows I like being her little sissy slut house girl and maybe it's time to get the hair extensions and boob job she has decided I need so I can be Kandi full time! She is tired of waiting for me to change and that's what she is going to set up! Several weeks later I am in surgery getting "D" cups and signing that I agree to the size and want them as "part of my transition" and am not being forced in any way. When completed, Janet rewards me with a makeover, low cut tops to show off those beautiful orbs and extensions added so I can grow out my own hair and be the girl she always wanted me to be! A few weeks later, John calls to say they need a CPA at the law firm, and wonders if I would like to apply. Long story short, I get the job and work and live full time as Kandi with new ID and my own office! The fun is when John or George schedule a meeting to 'discuss me being bad' at work and I end up sucking them off. Don't you just love the office perks? John loves shoving his manhood between my tits while I suck him and I know my dress is a bit to 'clubby' as a professional at work, but I know it gets both men going and the young interns and paralegals wear similar outfits. The best is when Janet shows up for lunch and feeds me her come in a little hotel down the street as I still adore my wife and giving her mind shattering orgasms as her best girlfriend/lover.
My life is pretty much routine now, dressing sexy for my wife and boyfriend, treating them with my mouth or ass pussy whenever they want, keeping myself tanned with bikini lines, dressing sexy, keeping the house, 'working' at the office and being available for whatever the 3 may need. Janet, John and George take care of all the major plans and I am the sissy slut that does their bidding.
I love my new life!