My Unwanted Transition 13
I take a breath, cross my arms over my chest, then sit up again. Skylar is using his weight to keep my feet on the ground. His hand is hovering just over my knees, holding a small object. Inside the black square, my eyes focus on a ring. Set upon the top rests a large, dark diamond, and the white diamonds around it grab my attention. I place my hands on the floor and sit myself up properly, my heart ready to burst through my rib cage as I realize what’s happening.
It feels like there are spotlights on me, and everyone in the gym is watching. I quickly look to the side, but everyone seems to still be going about their business. Excitement and worry overwhelmingly run through me. There’s no way for me to contain the emotions, so they convert into tears, which start to spill from my eyes. My brain is spinning like tires on ice, trying to gain traction to formulate a thought. I picture us together, having a wedding, being his wife, and him being my husband. His scent enters my nose as I breathe in, reminding me of the comfort his presence gives me. I breathe out, then answer.
“Yes,” I say softly.
Skylar takes the ring with one hand, then carefully holds my finger as he slides it on. The black band glides down my finger, over my knuckle, and settles firmly at the base. A few people around us give their congratulations, but I’m only interested in kissing him. I put my arm around his neck and pull myself forward until our lips meet. This memory etches itself into my brain like writing on stone, our first kiss as being engaged.
“Do you want to finish?” He asks.
I shake my head, then wipe my eyes on his shoulder. The only thing I want to do is go home with him. My legs are weak, so I take his hand and have him pull me to my feet. Even having to leave his side to get my belongings from the locker room hurts. I grab my stuff quickly, then rush back to him. In the car, I hold my hand out and look at the ring adorned on my finger. I have no idea why he wants to marry me, but I don’t doubt his love for me either.
Leslie is waiting in the living room when we get home. She looks at us as we come in but doesn’t say anything. Then, when she notices the ring on my finger, she jumps up excitedly.
“You said yes!” She blurts out.
“You told her?” I ask Skylar, and he smiles. “I did,” I answer, my mouth almost stretching ear to ear.
Leslie hurries toward me, wanting to see the ring. I hold my hand up so she can look. Her eyes lock on the diamond, and she dances in place. Her hand holds my wrist, pulling it closer, and I take the time to examine it again as well. It makes me think about my entire life. I had thought about being married to a girl and ways that I might propose one day. After the change, it never crossed my mind that a guy would propose to me.
“We’ll have to talk more about it later,” I say as I take Skylar’s hand and walk.
I lead him to our room, then strip down from my gym clothes. I’m not exactly horny, but I have the urge to have sex with him. My emotions are boiling, needing a release, and making love is the best way I know how. He’s usually the dominant one, and me, submissive. Our roles switch for now as he follows my lead. I push him to sit on the bed, then I straddle his lap and ride him. My hands hook his shoulder and neck, giving me leverage to drive my body against his. I don’t slow or stop until I make him cum. He shudders beneath me, blasting his load into my body.
We hold each other in that position long enough for him to go soft. His cum messily leaks from me, but we love making a mess with each other. He lies back, pulling me down to rest on top of him. As I listen to his heartbeat, I think about our future. We’ll have to plan a wedding, then I’ll be his wife, and he’ll be my husband. Until then, I will be his fiancé. Be his, I think about that more. The thought of him possessing me like a prize always stirs a warmth in me. It’s like arousal, but much deeper, so strong that it scares me, so I never act on it. It’s crept into my dreams before, being his, his good girl, or bad girl, his submissive little slut. I’m already submissive to him, but I don’t think he’s caught on to how much I’m willing to be.
We eventually get up to clean and shower. We shower together, something we love to do, though we don’t often do it. I then go and tell Leslie about the proposal. She asks for every detail. After going over the entire story three times, she’s satisfied enough for now. For the next several days, she asks me to tell it at least once. On my day off, I finally call my parents and give them the news. Thankfully, both of them are supportive. They press me to make sure I keep them up to date about our wedding plans.
I’m just finishing up at work when Jen calls me. We don’t get together as often as we used to, but I still consider her my best friend. I’m usually busy with work or planning the wedding with Alice. And, with Jen and Skylar living together, I know she’s busy too. Jen asks to meet up, which is good because I need to ask her about being my best man, or in this case, my best gal. My wedding is only three months away now, so I need to make sure everything is in place.
I meet Jen at a café that we used to always hang out at. On one side, they serve mediocre food, but the reason we always went there was for the arcade. Before we each share our news, I convince her to play a few games with me. Our short gaming session brings smiles and frustration, and most importantly, reminds me of our long friendship.
“You won, so why don’t you share first,” I say as we sit down.
“I did win, so I should choose who goes first,” she says, smiling. “I’ll go, though. Skylar asked me to marry him,” she continues, then lifts her hand to show me the ring. I can’t believe I didn’t notice it earlier.
“Congratulations!” I say, smiling. I’m delighted to see her in such a good mood.
She goes on to tell me about the gym, how Skylar proposed, her feelings, Leslie’s reaction, and her parent’s reaction. The expression on her face, her smile, the tone of her voice, they all burst with happiness and excitement, something that I was afraid she had lost. It’s been a long time since I’ve seen her like this, and I love it.
“So, your turn now!” She says.
“Actually, I want to talk about marriage too. My wedding with Alice is in three months, so I wanted to ask you to officially be my best gal,” I say.
“It would be my honor,” she says, bobbing her head in a playfully dramatic manner.
We discuss my wedding further. She also asks me to be the best man when she gets married, and I agree. The topic changes to my bachelor party, which I’m not sure I want to have, but she convinces me. I agree to a small get-together with some friends, then we come up with some basic plans. Before we part, I give her a hug. I notice how much she’s changed physically over the years. If I were meeting her for the first time, there’s no way I’d know she was ever a male.
As I drive home, I think about Jen more. The memories of us experimenting come to mind. I remember how she masturbated beside me, how she jerked me off, and how we eventually had sex. The thoughts arouse me, so when I arrive home, I masturbate. I know Alice will be back soon, so I pull up some pics of Jen and stroke myself. Her social media pics help, but I want more, and I know I shouldn’t. I open the hidden folder on my phone, which contains several nudes of Jen. One part of my mind tells me it’s wrong, but I can’t help how good it feels. I was first, the first one to be inside her, first to make her cum, and first to cum in her. My cock throbs then erupts, blasting my cum into the air, as I gaze at her naked form on the phone. Just like each time before, I contemplate deleting the pics, but I can’t bring myself to do it.
It’s about a month before Andy is set to be married. I host his bachelor party at my house, which made it easier to plan. Leslie decides to accept Alice’s invitation to her bachelorette party, which she also has today. Counting Andy, Skylar, and myself, there are ten of us at the party. Most are people we knew back in school, and few others are Andy’s co-workers. I’m the only girl.
The guys start drinking right away, getting themselves into various drinking games. There’s also plenty of party snacks, from chips and salsa to cheese and crackers. In the dining room, there are a few people playing cards now. I watch the card game for a bit while listening to the other group doing shots in the kitchen.
Skylar comes over to me, appearing to be a little buzzed already. He has me follow him to where the others are drinking, apparently wanting to do a belly shot with me. I’ve made it a point to avoid alcohol and drugs since I’ve found myself in bad situations because of them. I decide to join in, only because both Skylar and Andy are here, so I feel safe.
The guys clear the table, and Skylar helps me to lie flat on it. He then pulls my shirt up until my entire midsection is exposed. I see the group form around me as Skylar pours the liquor on my belly. He takes my wrist, licks it, then sprinkles salt on my skin. Another guy hands me a slice of lime, which I place in my mouth. I feel Skylar lick my wrist before pressing his mouth against my stomach. His breath is warm, and the liquid is cold. I see his face come into view as his mouth meets mine. I instinctively put my arms around him, even though it isn’t a proper kiss.
Various forms of cheers and encouragement come from the group as he stands back up. Skylar gets a paper towel to clean me with, and already people are trying to up the ante. They want to see how far he’ll go or how much he’ll do and how much I will allow. All of a sudden, people have cash in their hands and are offering bets. Somehow, even though everyone’s talking over each other, they present a wager to us. One of them comes forward with a scrap piece of paper and hands it to Skylar. It’s a list of six things, six body parts to be more precise; neck, cleavage, navel, thighs, fingers, and feet.
Skylar has to roll a six-sided die, then lick the salt off of my corresponding part. The pool is now two hundred dollars, and they offer ten us dollars for each completion, which means Skylar will have to do twenty shots to get it all. More people come over as they hear the excitement. I’m sure the thought of seeing my skin gets people to put money forward. The pot grows to five hundred as now everyone at the part is around us. Skylar and I whisper back and forth, trying to come up with a plan. Luckily, the noise is plenty of cover for us.
“What do you think?” Skylar asks.
“I think fifty shots is a lot,” I say.
“Yeah, so do I, but it’s five hundred bucks,” he says.
“I have an idea, I say,” looking around at the group. Their wager doesn’t cost us anything, so I know all they want is a peek at me. I whisper my idea to Skylar, then he smirks and nods.
“We have a counter wager,” Skylar announces. “Instead of ten dollars a round, you give us fifty, and we will change cleavage to nipple.
The group, including Andy, all look around at each other. I wonder if Andy put money in, and if so, how much. Would he pay for a chance to see my skin? The group discussion continues, and I try to see how Andy feels about it. I keep my head low, but my eyes watch, and I try to listen to his voice. I see him lean in to talk to a co-worker. He doesn’t notice me watching, but I can’t hear what he says. A moment later, the same co-worker rallies the group to a new counteroffer.
“We will up each round to one hundred dollars, but you’ll have to switch navel to clit,” they offer.
Is that Andy’s idea? I think about that more than the offer itself. Fine, if they want to play hardball, I will too, and take their money. Before Skylar has a chance to discuss it with me, I announce my acceptance. He will have to roll the die five times and take five shots, then the money is ours. I tell the crowd to give me a few minutes to change, then I lead Skylar away with me. On the way to our room, I think about how I’m basically selling a chance to see me naked. As I calm down from the excitement of the crowd, I realize I’m partly aroused.
I’m a little buzzed, but not enough to impair my judgment. When we enter our bedroom, I stop and look at Jenny, making sure she’s really okay with this. I think about the last party she attended and the horrible things that happened to her. If she doesn’t want to do this, I will go back and call the bet off.
“Are you sure about this, babe?” I ask.
“It’s just five shots, then we will take their money for being perverts,” she answers, smirking.
“I know, but are you okay with-,” I pause. “Okay, with being exposed like that?” My voice lowers, and I think she understands what I mean.
“This isn’t like that,” she says. “I’m with you, so I can do it. As long as you’re the one touching me, I don’t care about anything else.” Her lips pull into a smile. “The question is, are you okay with licking my feet?”
“I love your feet,” I say.
“Is that right?” She retorts.
“That is right,” I say, then smirk, approaching her.
I lift her slender body, so she falls backward on the bed, then I hold her ankle in my hand. My other hand pulls the lace of her sneaker, loosening it until I’m able to slide it from her foot. I pull her sock off next, then press my lips to her sole. Her foot is long and slender with a high arch, and because of her good hygiene, she smells like lotion. Her toes are painted solid black, which is the color she always has them unless she has French tips or another special design. I have a little foot fetish, but I’ve always been too nervous to tell her or anyone about it, so I use this opportunity to break the ice, hopefully.
I hold her foot in my hands, then close my lips over her toe. Her leg tenses some, but I continue, then I stop a moment later. I look down her leg to her face, and she’s looking back. Her expression doesn’t carry disgust or judgment, which is a relief to me.
“I didn’t know you liked my feet that much,” she says.
“I do,” I respond, hoping she can put the rest together.
“I’ll keep that in mind,” she says. “We should get ready to head back, though.”
She undresses down to her bare skin, then pulls a robe on and ties it. Five rolls, I think to myself. They might have paid to see her, but there’s also a chance they won’t see much at all. My cock jumps at the thought of licking her clit in front of them. With Jenny having such a huge sex drive too, I wonder if this turns her on at all. When she’s ready, we head back downstairs.
I make quite an entrance in my robe, wearing nothing else except for flip flops. Already, I notice several of them drop their eyes down my body, probably hoping to get a look at an exposed part of me. We clear the table in the dining room, which is larger than the one I set up in the kitchen. Skylar helps me settle down on top of the table, then he’s presented with the updated list. It’s now, neck, nipple, clit, thigh, fingers, and feet.
Skylar rolls the die; it bounces across the table beside me and slides to a stop. I carefully adjust the robe to expose my stomach. Skylar pours the liquor on me, then places a lime slice in my mouth. He salts my neck, then licks it from my skin before moving down to slurp the liquid in the crevice of my torso. Even while playing this game, he uses his mouth on me in a way that feels incredible. With the liquor sapped up, he comes for the lime. That’s one roll and one hundred dollars down.
There’s a pause as someone asks to do the pour, and another, the lime. I think they now realize how much money is being spent on us and want to get more out of it. I tell Skylar it’s okay, so two of them step up, and one pours the shot on me while the other has the lime. I look at the guy holding the lime slice; his name is Nick, a former classmate of ours in school. He’s also one of the few people from my past that know about my change. Andy stayed in contact with them more than me, so I told him it was okay to talk about it.
Nick has short, light hair and green eyes. I notice that he’s kind of attractive, so I take him by the wrist and guide him as he places the lime in my mouth. I curl my tongue around it in a teasing manner and look at his face. I’m not sure if he put any money in or not, but I will give everyone their money’s worth. Skylar rolls, again and again, he gets my neck. I hear some sighs of disappointment come from the group as Skylar takes the shot from me.
Two more move in to set the shot. Andy has the lime this time, so I part my lips and let him place it himself. He does it gently, almost as if he’s afraid to hurt me. As he pulls his hand back, his fingers brush my cheek, and I try to keep from blushing. Skylar carries out the second shot, then takes the next hundred dollars from them.
As with Nick, I hold the next guy's wrist, one of Andy’s co-workers, as he places the lime in my mouth. Skylar rolls the die, and this time there’s a little more excitement as it lands on thighs. The heat of my arousal has already been slowly building just from being on display. I anticipate Skylar licking the inside of my thigh, and that makes it worse. He pours the salt, then runs his tongue over my sensitive flesh, and quickly moves to my stomach. I know I’m definitely getting wet now.
Roll number four is fingers, and the disappointment of the group grows even more. Four hundred dollars have been given to us without them being able to see anything. The room gets quiet for roll five, each person probably wishing their hardest to see one of my girly parts. As Skylar tosses the die, I find myself hoping that I can show part of myself off to them. I think about Skylar pulling my robe open, exposing my breasts, licking my nipple, all in front of them. More heat rushes into my loins and makes me throb. The dice lands, and for the third time, it’s my neck.
The group loses attention before the shot is even finished. Skylar shows me the five hundred dollars, then we share a proper kiss. I can see most of the guys are defeated, which makes me feel bad. This is a party I planned for Andy to be a celebration of his upcoming marriage. I take Skylar’s hand and lead him aside so I can whisper in his ear.
“Maybe we should give them a little show,” I say.
“What do you mean?” Skylar asks.
“You know, open my robe and do a shot on me,” I say.
“Do you really want to do that?” He asks again.
“I’m okay with it if you want them to see me,” I say, my voice becoming submissive.
“Let me show off my fiance’s sexy body then,” he smirks, then kisses me.
I wait for Skylar to gather everyone together again. Their energy returns once they hear what we plan to do. I lie on the table, then Skylar unties my robe. His hands pull it open, exposing my nudity in an instant. I can feel everyone’s gaze on me, devouring my flesh. Our former classmates are in disbelief that I have such a woman’s body, from head to toe. I pull my legs up, so my feet rest flat on the table, far enough apart so that everyone can see all of me.
I use my hands to push my breasts together, making Skylar spot to pour the alcohol. He sprinkles the salt between my legs, but it’s more for show than anything. His hands hook around my legs as he lowers his head, his tongue reaching, then touching my folds. He licks me, his warm, spongy appendage pushing between the lips of my womanhood, moving upward until he reaches my clit. For a moment, I forget about everyone watching, and I put my hand on his head. It spurs him to continue a bit longer, but he eventually pulls away to move on. I’m both disappointed and thankful because I would have let him make me cum right here, with everyone watching me.
As he moves up on the table to get the liquid between my breasts, I know it’s sturdy enough to hold us both due to our past playtimes here. There isn’t much of a pool of the liquor left, though, as it’s spilled down my body. Skylar improvises, licking it from my skin, between my breasts, around them, then both of hard nipples. I spit the lime from my mouth, wanting a proper kiss. His tongue shoves into my mouth, and we share the taste of everything. When we both come to grips that we can’t go any further without having sex, we pull apart, then I tie my robe back on.
“The peep show is over,” I say.
Getting to see Jen naked again fuels a hunger in me. Her breasts are so much larger than before, perfect, and the way her face looks when she’s in pleasure. My cock is so hard I can’t even concentrate. I force myself to continue participating in the party, knowing how much effort Jen put into it. My plan to see her naked with that game worked better than I could’ve imagined, even though it cost me two hundred dollars.
When I see Jen go upstairs, I follow a minute later. I arrive to see her bedroom door closed, so I assume she’s getting dressed again, and I wait. A few minutes later, she opens the door, then stops as she sees me waiting. She smiles at me, likely happy to see her best friend, but with my cock throbbing in my pants, I can only picture her naked.
“Hey, Andy, what’s up?” She says happily.
“Uh, can we talk for a moment?” I ask.
“Of course,” she says, then leads me into her room, closing the door.
As soon as she turns around, I step toward her, my body keeping her against the door. I feel a slight pain, knowing I’m about to destroy her trust in me, but I need just a little piece of her. I press my mouth firmly upon hers, my tongue surprised to find her mouth opened as it enters. She’s completely still for a moment, then her tongue meets mine. I can’t believe she’s kissing me back; it makes me hot, makes me throb. I reach under her shirt, craving to feel the perfect breasts I just witnessed downstairs. She moans softly into my mouth as I squeeze her soft flesh.
My intention was just to have a kiss, something to give me closure, something to masturbate to. She doesn’t stop me, doesn’t resist. I lift her shirt, then her bra, now getting a better look. She still doesn’t stop me as I mouth her nipple, and her body shivers. My hands unbutton her pants, pull the zipper down, then I feel her hand land on mine. I look up at her, and she shakes her head. The hand she uses to hold mine contains her engagement ring, the mark of her commitment to Skylar.
I step back and calm myself as she fixes her clothes. She approaches me again, standing close, her eyes looking into mine. I think I see the same craving in her eyes. She tells me that we can’t do this, that we’re both with good partners, but I already know. I nod, then she leans forward and kisses me; our tongues meet again, her lips sucking on me, then biting my lip softly as she stops. I tell her I’m sorry, then leave toward the bathroom to put cold water on my face.
I stand in the middle of my room, dazed. Andy’s advance on me sparked something I locked away a long time ago. I close my eyes, trying to hold back tears. Why, why did he have to do that? My feelings for him were kept securely in a box, stored deep inside me. Then, like a master key, he unlocked it.
Skylar comes in a few minutes later, seeing me standing there, probably looking like a mess. Worry fills his face as he sees me crying. He holds me, using his fingers to wipe my cheeks.
“What’s wrong, my love?” He asks, rocking me in his arms.
“I’m sorry,” I say with a raspy voice.
“Sorry for what?”
I take a deep breath to calm myself, then pull away from Skylar, having the feeling I don’t deserve his love or attention. I feel his eyes on me as I look at the floor. He waits a moment, then asks again, worry filling his voice now.
“I made out with Andy,” I say, then I feel it all spill from me. “He came in here and kissed, and I kissed him back. I let him get my shirt off before I finally stopped him.” Heat rushes to my eyes again, forcing more tears out. “I didn’t want him to stop,” I add.
Skylar is quiet, which makes me nervous. I just kissed the person that I left him for before. He’ll probably break up with me now, then I’ll be alone again with my ridiculous sex drive, making bad decisions. I hear him sigh, the signal that I ruined not only our engagement but our relationship too. I’m ready to give the ring back if he asks for it since I don’t deserve it anyway.
“Do you still have feelings for him?” He asks.
“I think so, but I didn’t know it until now,” I answer.
“I understand,” he says. “I can’t say I’m okay with it, but I do understand. You’ve been friends with him for a long time, then the dynamic of your relationship changed when you became a woman. And, your first experiences were with him.” He pauses, then asks, “why did you stop?”
“I stopped because I love you. As much as I want to have sex with him again, I don’t want to lose what we have,” I answer. “Are you going to leave me?” I ask.
“No,” he smiles, “I’m not leaving you, don’t worry.” I feel relief. “You owe me, though.”
“I’ll do anything,” I say.
“Good, because I already know what I want,” he says. “I want to film you masturbating.”
“I’m yours to film,” I say, my submissive side taking over.
“Are you mine to do this?” He asks, slamming his palm down against my butt. I wince and nod. “What about this?” He smacks the other side, and I nod again. “And this?” He curls his fingers into my hair, tugging my head to the side, then sucking my hard.
I return to the party with his mark on me, which I proudly display. People start to leave one by one, and I imagine them picturing what’s under my clothes as they do. The thought of some of them thinking about me as they masturbate sends warm arousal through my loins. How many of them got hard as they watched Skylar feast on me. Guilt fills my rational thoughts, even as my arousal grows. I just kissed Andy, and now I’m thinking about a group of men jerking it to me.
When everyone is finally gone, Skylar approaches me, taking me to the table. He undresses me, and I already know what he wants to do. As I lie on the table, I imagine the group standing around us as Skylar penetrates me. I’m physically horny, but I’m not entirely into it. I put my legs around Skylar, encouraging him with a moan, wanting to make him feel good. My brain tries to manage my pleasure and guilt. Why does being on display turn me on so much? I shouldn’t want anyone but Skylar to see me.
“You don’t seem all here,” Skylar says as he slows down. “Are you okay?”
“Not really,” I answer. “But don’t stop.”
I force myself to only think about Skylar. He deserves my full attention while we make love, not just some shell of me. I think about how he put his mouth on my foot earlier and admitted to having a fetish. My mood improves some, then I bend my leg to place my foot on his shoulder, pushing him back. He looks confused at first, probably thinking I changed my mind. I bring my socked foot to his chest, dragging my toe upward until he finally grabs my ankle.
His face fills with desire, an expression he only makes when he wants to ravish me physically. I’m surprised by just how much teasing him with my foot spurs him on. I wonder if it’s the same arousal that fills me when I think about people watching me.
Skylar continues to fuck me, but my mind isn’t in the right place to reach an orgasm. I try to encourage his pleasure with my moans, by pulling him with my legs and feet, and by moving my hips. His breaths become shorter as he gets closer until he finally pulls out and explodes on my stomach. We clean ourselves and the kitchen, then settle into bed.
“Skylar,” I call his name softly.
“Yes, babe?” He responds.
“I need to tell you something,” I say.
“Is it about Andy?” He asks.
“No,” I answer, “well yeah, kinda, but not only about him.”
“What’s wrong?” He turns to face me.
“I liked all those people watching me, us,” I say outrightly, having thought about it for a while now.
“Like, the shots game?” He asks for clarity.
“Yes,” I answer.
“I liked it too,” he says.
“I didn’t just like it,” I say. “It turned me on.. a lot.
“That’s what I meant,” he says. “I like it that way too; that’s why I like recording us.
“So, you don’t think there’s anything wrong with me for wanting them to see me naked?”
“I figured you liked public stuff a long time ago when you helped me get off in the back of the car. Not to mention the pictures you post online.” He smirks. “Are you just now figuring out you like exhibitionism?”
“Yeah, I guess so,” I say.
“Don’t worry about it. As long as you practice safety, it’s fine.”
“I need you to help me,” I say, almost pleading. “I make bad decisions when I’m really horny, especially right before my period. I trust you more than anyone.”
“You’re gonna worry yourself to death,” he says. “But, if you think it’s important, we will talk more about it and come up with something.”
Alice just finished telling me about her party and how her friends hired a male stripper. She didn’t think much of it and assumed my party was going to have a stripper too. I start telling her about my party when she finishes, explaining that we didn’t have a stripper. She’s surprised, but I tell her to wait until I finish, knowing that the part about Jen will come soon. I do my best to fill in all the details, then move on to the drinking game.
The image of Jen naked on the table fills my mind as I give the story, making me rock hard. I tell Alice about it all, but I don’t tell her I put money into it. She doesn’t seem to mind, not yet anyway. I think of the kiss I still have to tell her about, the kiss I gave Jen in her bedroom. When I finally get to that part, I can’t bring myself to own up to it, so I tell her that Jen kissed me. I see Alice’s expression change to one of disappointment and annoyance. Her face softens after a minute, then she asks for more details. I tell her that I instinctively kissed back and that I liked it because of unresolved feelings I have for Jen.
“Be honest. Did you two do anything else?” Alice asks firmly.
“No,” I say quickly. “We just kissed.”
“It must’ve been good since it made your dick hard again,” she says, looking down to the shape pressing through my shorts.
“I’m sorry,” I say. “I’ve known Jen for a long time, then when she became a girl, it caused me to feel all sorts of things.”
“I see she’s still causing you to feel things,” she says, sighing. “Is this something I should be worried about? She’s kissed you once already.”
“You don’t have to worry; it was just an isolated incident,” I say.
“You say that, but it isn’t like you’re gonna stop seeing your best friend. What if she tries again?” She pauses then speaks again before I can answer. “How can we resolve this for sure?”
“I don’t know, have sex with her?” I say jokingly.
“Maybe you should,” she says.
“Are you serious?” I ask, sitting up.
“I am. If she wants you that bad, and you still have some feelings for her too, maybe it's best to get it out of your system.”
“Even if we do decide to do that, I don’t think Skylar would like it,” I say, though the thought of getting with Jen again is exciting.
The idea bounces back and forth for a few minutes. I can’t believe my own fiancé is encouraging me to have sex with my best friend. Still, I feel a tug of guilt for lying about how the kiss happened, and I wonder if Alice would feel the same way if she knew I initiated it. The guilt continues to circle my thoughts as Alice moves on top of me, taking my ill-gotten erection and putting it inside her. We’re both still fully clothed, with our garments moved just enough for our genitals to connect.
“Do you really think it’s a good idea?” I ask again.
“Do you really want to talk about Jen while we’re having sex,” she says.
“I’m just wondering how we’ll get Skylar on board,” I answer.
“Maybe I’ll have sex with him in return,” she says, stopping. “You fuck Jenny, and I’ll let him fuck me.”
Alice remains still, looking down at my face, my hard cock trapped in her pussy. I can feel her eyes trying to gauge what I think about it, probably wondering if I would trade her for one more time with Jen. She has me in the worst possible position, but I brought it on myself by pressing the issue.
“Well,” she says, moving her hips up and down one time. “What do you say? Your wife to be is willing to offer her own pussy just so you can fuck your best friend,”
“I don’t know,” I say.
“Which part? You don’t know if you want to fuck Jen, or is it Skylar fucking me?”
“Do you want to have sex with Skylar?” I ask.
“Maybe thinking about his dick gets me wet, just like Jenny gets you hard,” she answers. “Make a choice, or I’m just gonna go to bed now.”
“Okay, let’s do it,” I say, not wanting to lose my chance.
“Fine,” she says, but giving no clue as to whether she likes it or not.
She leans forward for balance, then drives her body up and down on mine. The way her pussy slides so fast along my cock feels incredible as always, but I can tell she wants me to cum quickly. Her hands hold mine, keeping my arms pinned. She moves her hips up and down and back and forth until I finally cum.
I find it hard to sleep as I think about Alice’s offer. Based on my lie about the kiss, she’s willing to set it up, so I have a chance with Jen again. I know it’s wrong, but the best part is that Jen won’t know about any of this. I might have a chance to have sex with her while she thinks it’s Alice and Skylar’s doing. The thought of Skylar with Alice gets pushed aside each time I think of being with Jen. I don’t know why it turns me on so much, especially since Alice is absolutely sexy. Though, I suppose it’s because of our friendship and her being like a forbidden fruit. I keep trying to fall asleep while thinking about Jen and what I want to do with her if I get the chance.
I spend the next week with Leslie looking for a dress for Andy’s wedding. It has to be something pretty, but it can’t stand out too much to take attention away from Alice. I think about how soon it will be before I’m looking for a wedding dress. The black diamond on my finger is a constant reminder of Skylar and our commitment to each other.
I eventually settle on a dress to be Andy’s best girl, which has to be slightly tailored to properly fit my figure. Against my protests, Leslie leads me to a bridal shop to take a look at wedding dresses. She wants me to try some on, but I’m not ready for that yet. Skylar and I haven’t even set a date, nor made any plans past the basics.
When we get back home, I start to make dinner, hoping to have it ready in time for Skylar. There are only two days a week when he gets home early enough to eat together, so I like to take advantage of that. Skylar arrives before I finish, then helps me with the rest. The meal is chicken alfredo, and as I finish with the sauce, I dip my finger in a little, then place it on his lips. I feel flirty, horny, the same deep desire I always get when I ovulate a couple of weeks before my period. My sex drive is naturally high, and this time of the month makes it even worse. I wonder if this is what an animal feels like when they’re in heat.
I make more flirty and sexual comments as we eat, but Skylar doesn’t play along like he usually would. I assume he isn’t in the mood for sex today, and even though I know he would do it if I wanted, I’m not going to press that card. Since making that sex agreement, we’ve each used it once, both times ending happily. After we finish eating, I start cleaning up, wanting to get everything put away so that I can go masturbate in the shower.
“So, I talked to Alice the other day, and I’ve been trying to figure out how to discuss it with you,” Skylar says as we clean up.
“Alice? Is it something about their wedding?” I ask.
“Not directly, no, but it is about relationships,” he says.
“What about them?” I ask, getting more curious.
“To put it plainly, she thinks you and Andy should have sex,” he says, almost as if it’s something normal to say.
“She wants me to have sex with her fiancé?” I ask, confused.
“Well, she made some excellent points,” he says. “The two of you are close, and there’s obviously still some unresolved feelings based on the kiss. So, she thinks, and I kinda agree, that sex will get it out of both your systems.”
“We’re not pets in heat, Skylar,” I say. “I’m gonna be your wife, and Andy is going to be her husband.”
“Jenny, listen,” he says. “I’m not telling you to do it, but I understand what you and Andy have and share. It’s strong enough that you broke up with me before, and if having sex with him again will make you feel good, better, then I will support it. I don’t want you to have to forever linger on that kiss and what it could’ve been.”
“What am I supposed to do then, just call him up and tell him to come fuck me? Or like, are you and Alice gonna watch? I say sarcastically, feeling annoyed.
“Please don’t get upset. Here, let’s sit so I can explain everything properly. Andy told Alice about the kiss, and we both know that you and Andy are close and have had an intimate relationship before. All we want to do is offer you two the chance to try and resolve those feelings. You can say yes, or you can say no; it’s up to you.”
“I don’t know. I’ve gotten myself into so much trouble and drama because of my hormones. Being with you helps me keep them under control; you keep me level.”
“I’m not worried. I trust you,” he says.
“You’re giving me your blessing to have sex with my best friend, the same one that took my virginity. Of course, I want to have sex with him, but I’m scared that it won’t resolve our feelings, but make it worse. Would having sex with your first help you?”
“I guess I don’t know. But there is one more thing. Alice also said to make it fair, that she and I would have sex too.”
“Oh, so she wants to help Andy and me by having sex with you. What did you say to that?”
“I just told her that I’d have to discuss everything with you, that’s all.”
“Well, do you want to have sex with her?”
“I suppose I wouldn’t turn down the chance.”
“No, do you want to?”
“Okay, I do.”
“Just so I understand then; if I get with Andy, then you and Nicole get to have sex too?”
“That was her offer, yes.”
“This is more like couple’s swinging than anything, then,” I say, feeling myself calming down.
“It is kinda like that, I suppose.”
“It isn’t just my decision then. We should decide together.”
We talk about it at length, even writing down ideas to add to Alice’s proposal. My fetish for exhibitionism makes its way into the ideas, forming into the suggestion that we have to record our respective time with each other. Skylar and Alice get to watch my time with Andy, and we get to watch theirs. I also add that it should be on the same day, and we can opt to hang out beforehand to make it feel less robotic. When we finish, I leave it with Skylar to communicate back to Alice.