How Marissa Became a Woman

This is a work of pure fiction. It deals with adult subject matter including crossdressing, and consensual male on male sex. If any of this offends you, please stop reading now.

This is my first story for others so any feedback would be appreciated.

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Henry and Lisa have been married for many years. During that, time both of them made many little personal discoveries. Among them was Henry's passion for crossdressing. When it came out, Lisa was shocked, but understanding. She did not threaten to leave him. Instead, they talked about it objectively. Seeing him in his feminine clothing did not arouse her. She accepted that he needed this in his life and that she could not deny him this. So they agreed to a compromise.

One weekend a month, Henry could wear openly any and all feminine items of clothing that he wished. It started innocently enough, underdressing in just panties, and tights or pantyhose. Slowly over time, Henry began to explore the fullness of his desires. Lisa while not turned on in the slightest, wanted her husband to enjoy his weekends, so she started coaching and helping him to be more feminine in appearance, and mannerisms while dressed. Soon, she began to feel comfortable thinking of Henry more as a woman. He became her girlfriend.

They mostly hung out around the house. She managed from time to time to get him out of the house in clothing that, except under scrutiny, looked masculine. She began calling him Marissa. So Marissa and Lisa became great girlfriends spend each of her weekends together. It wasn't long after becoming Marissa, that she turned the conversation to Lisa and her fantasies and desires, over some wine one evening. Lisa seemed to feel that she could confide in her girlfriend and the conversation broached many interesting topics, from anal, roleplay and BDSM, to lesbian and gay fantasies, as well as many straight fantasies involving other men.

Marissa let slip her fantasies too during this conversation. For the next couple of months nothing changed. Then one weekend, Lisa took the Friday off from work and put a plan into place, providing Marissa a special night with new clothes and some hot make out session. Lisa revealed her desire to take Marissa with a strap on. Marissa knowing that this was part of both their fantasies to explore eagerly accepted and soon Lisa was pounding Marissa roughly every month, and sometimes in between as Henry too. This again seemed to reach a plateau where they were happy, everything was smooth they were enjoying many aspects of Henry's desires and found a few new ones for Lisa. She never forgot the conversation about fantasies with Marissa and was determined to help her husband live them.

It was Henry's weekend, and Lisa had made plans for them. Once Henry became Marissa, she would get her dressed to go out this time fully as Marissa. When Henry got home, Lisa had him take a shower and shave everything closely. When he got out, she helped to towel her dry and apply lotion all over her body. This caused some amorous tendencies that Lisa had to squash and keep them on track. She had Marissa put on a matching black silk and lace bra and bikini set. She produced some breast forms to fill out her bra. She had her put on a black garter belt and stockings to match the rest of her lingerie.

Once she was done with that, she sat her down and went to work on her makeup, taking time to accentuate her face in the right way so as to enhance the femininity. Once she was satisfied with the makeup she helped her into a floral print dress with a skater style skirt that fell just slightly above the knees. Next came the 5 inch heels, and her purse which Lisa had put all of her ID and important needs during her shower. They were ready to go out on the town. Marissa was a nervous wreck shaking and looking all around as they left the house.

"What if someone sees us?" she wondered.

Lisa reassured her, "Anyone looking would see two women out on the town for the night and nothing more. However, we are going to a drag show so there shouldn't be anyone there that we know. Even if we do they will not likely say anything because of where we are."

They made it to the bar without Marissa fainting although she was almost hyperventilating. She was oblivious to the stares as they made their way into the bar and found a small table to sit at. Lisa ordered them some drinks. Marissa took the first drink and slammed it, causing first a small head rush and second a reproach from Lisa on how to drink properly, by sipping through the straw. When the second drink arrived, Marissa sucked down about half before Lisa stopped her again. "Slowly" she chided again, "We have all night, just relax, and enjoy the show."

Soon enough the floorshow started and drag queen after drag queen took the stage performing, and showing off their assets. Marissa had begun to relax, and enjoy the show, when a man walked up to the table and asked if he could join them. She looked horrified at Lisa who calmly said sure. He asked what they were drinking and ordered a round for the table. As they sat sipping their drinks and generally chatting, Lisa told him that they were sisters and Marissa was single and she was married but they weren't really looking for anything but a good time tonight. He graciously acknowledged the let down with a smooth comeback about how about we just enjoy the evening as it comes with no expectations one way or the other.

Smiling they agreed and after several more drinks they managed to get Marissa on the floor with Gary. They danced for several numbers Marissa losing quite a few inhibitions to the alcohol and to all the attention from Gary. She was grinding on him and generally being a giant cock tease. When they returned the table she grabbed Lisa and went to the ladies room, after doing their business, she was frantically trying to get Lisa to get them home before he expected her to do something that she wasn't able to do or he found out she was a man and hit her or something. Lisa calmed her down, knowing that some of it was the alcohol but also knowing that she had the server dilute her drinks so that Marissa was more in control than the alcohol, she just did not realize it. "Just let it happen, nothing will happen that you don't want."

Lisa led her back to the table, and she looked at Gary, "Gary, Marissa here wants to take you home with us, I told her as long as you were OK with it, that you and her could use our spare room for the night but I will not be joining you two. What do you think?"

Marissa's mouth dropped open and Gary pulled her close and kissed her fully on the mouth with lots of passion while caressing her side and back. "Okay"

He paid their tab, put his arm around Marissa waist, and walked with the women out to Lisa's car. He opened the back door allowing Marissa to get in. She flashed her stockings as she slid in. Then he went around and slid in next to her. Lisa drove, as she drove she couldn't help but watch in the mirror as Gary gently and loving made out with Marissa. At one point as he was kissing her neckline gently, she moaned and pushed him away, "I can't do this, I'm... I'm... I'm a man."

He looked her in the eyes, and said, "I know" and brought her in for a passionate kiss. Fortunately, they were not too far from the couple's home. Gary and Marissa were almost inseparable, kissing, touching running hands over clothing and skin where they could touch.

Lisa motioned down the hall. "Why don't you take her to the bedroom?" It was a short trip down the hall, Marissa lost in the feelings flowing through her.

Once in the bedroom, Gary steps up his advances a little holding her firmly about the ass while kissing her, gently rubbing her through every stich of clothing, caressing her legs, above and below the skirt. He gently guides her to the bed, where he lays her down while continuing to make out with her. Marissa lets him take the lead just enjoying the attention that he is giving her and the sensations that he is providing, her panties are soaked from the amount of precum she has leaked during his ministrations. Looking up briefly from Gary, she sees Lisa leaning on the doorframe watching. They make eye contact, and Lisa nods gently letting Marissa know that it's OK.

Gary begins a slow wandering caress of Marissa body, her legs, and ending up with her skirt pulled up above her waist, as he kisses his way to her panties. She parts her legs for him as he works to reach the tucked member hidden there. He kisses the hidden cock gently pulling her panties from her hips. She lifts slightly allowing him to remove them completely. He leans back in and licks the tip of her cock tasting her precum, eliciting a moan from her. He kisses his way down from the tip to the base and then between her legs, licking and kissing behind her balls where all that precum has been.

Slowly he pushes her legs up, giving him complete access to her. He kisses her hole, gently barely touching her, but sending electric shock through her, causing a slight jump and moan. He kisses to the left side and to the right. He traces her hole with the tip of his tongue, causing gasps and moans. Slowly he flicks his tongue over her hole, just barely touching her, she shudders and moans. He slides his tongue in slowly, gently allowing her to set the pace by her reactions. Soon his tongue is buried in her and she is moaning. She moans out "Eat me baby, oh God! Don't stop."

Being a gentleman, he doesn't he continues rimming her, and sliding his tongue in and out of her watching her hole expand and contract as he probes her gently with his tongue. After about ten minutes or an eternity depending on which side of the tongue you were on she lets out a deep guttural groan, and lays limply for a minute. Worried, Gary looks back to Lisa, "It's OK, she just had an orgasm. She will have more just keep going."

Gary nods and gets up leaning over Marissa and kisses her fully on the mouth, their tongues dance and she moans into him. He uses the lube from the nightstand, warming it before he lays his first finger at her entrance, she does not flinch, and he gently caresses around her hole, allowing her to get accustomed to his presence down there. Kissing and nibbling on her neck and ears, while he works slowly to rub her hole. After mere moments the finger slips into her, she gasps.

He stops, and soothingly says, "It's ok beautiful, I promise I won't hurt you." He firmly places another kiss on her, working that finger into her. He works the finger until there is no resistance then adds the second, repeating the circling fingers, and gently allowing her to open to him. Soon he adds a third. She is panting and moaning at the fingers as they gently work her hole. He pulls them out and she lets out a pleading moan at the emptiness.

He kneels between her legs and places his cock at her entrance. She flinches knowing what is coming, he again soothes her, "It's ok beautiful, I'm going slow and promise to stop at any time you want." He gently pushes into her hole, well relaxed from his fingers, slipping the head in easily. She gasps from the initial intrusion. He leans up and kisses her. When she is ready, he slides in to her.

She eagerly accepts his cock, as it slowly works into her. Gently he bottoms out, staying there kissing her and telling her how tight her pussy is, and how he is going to make her cum. He then begins a gentle love making, sliding his cock in and out not fast and not super slow, but a pace that allows him to kiss fondle and caress her body while he fucks her. Only Lisa would have any idea how long he kept at her with this steady delicious rhythm.

Marissa had two more orgasms. The second of the night caused her to spasm as if she was having a seizure or something. This caused him look to Lisa for confirmation again that this is OK. With her hand buried in her panties, she assured him Marissa was fine. When the third orgasm hit her, he was ready and kept a steady rhythm through it, causing her to ejaculate shooting her load well over her head and down her chest as she spasmed. This was enough to send Gary over the edge and he shot his load into her, pump after pump, while she emptied herself onto her stomach.

After their climaxes, he rolled off her, climbed behind her, and spooned up to her drained and utterly relaxed body. Lisa pulled the cover over them, kissed Marissa on the forehead and went to bed. Sometime in the night, Gary makes love to her all over again, she has more earth shattering orgasms and he cums deep in her hole again.

The morning finds them at the kitchen table. Marissa is still in her dress, hair, and makeup a mess. They are talking as they wait for the coffee to brew. Lisa begins the conversation, "So how did you enjoy last night Marissa?"

Blushing bright red, she looks at Gary then Lisa, "It was wonderful, Gary was such a gentle lover and the orgasms he gave me, oh I feel so high right now. I don't know what came over me," she looks down, and begins to sound depressed, I am sorry Lisa, I didn't mean for this to happen, I-"

"I meant for this to happen." Stunned Marissa lifted her head and gaped at Lisa. "You remember our conversation a while back about fantasies?"

After just a moment, Marissa nods, "Yes."

"Well after we began exploring those I decided that you needed to feel like a woman and have your deepest fantasies fulfilled. I knew that you would never do something like this on your own, your love for me is to strong, and even if I gave you permission, you would not do it. So I planned the night out, I searched many of the crossdresser personal sites and found Gary.

I explained what I wanted and he was more than willing to help me. He enjoyed the pictures that I have sent him of you and could not wait to meet you. The drag show was the perfect place for you to feel at ease, and for him to make moves on you. I even worked with the server at the bar. Your drinks were watered down so you did all of that really without any appreciable drunkenness to blame it on. Also I wanted to make sure that you enjoyed and remembered your first time. It should be special for all women."

Gary nodded his head when Marissa looked at him for confirmation. "I... I don't know what to say. I felt sexy and flirty after a couple of drinks and just let things progress when I thought they had gone too far, you invited him home with us and I really didn't want to stop being sexy and flirting with him.

When he began making moves on me in the car, I was taken by the feelings that were running through me, I almost didn't tell him I was a guy. I was about to let him have his way with me anyway. When he said I knew it crushed the last of my resistance and I was his. He was so gentle and loving, nothing forced, everything sensual. It was everything that I could have asked for."

"Marissa, I am happy to know that I was able to provide what you wanted. Lisa had been very specific on how it was to be if you agreed to have me." Gary said.

Lisa looked to Marissa, "I believe that Gary can help fulfill a couple of other fantasies for you this weekend if you want."

"I'm not sure; I mean I loved what we did and really want more." She looked at Lisa with an apologetic look on her face. "He was so loving and there was so much more than just the feeling of the toys we usually use. I am glad to have experienced it, and if you never want me to do it again, then I-"

"I didn't say that you couldn't have it again. We will need to talk more before I agree to anything more than this weekend. For now, you have a willing partner and a wife that is allowing you to be all the woman that you can be with him."

Marissa looked into Lisa's eyes and all she saw was love. She almost started to cry, but was able to control herself. "In that case Gary there are two more things that I want to experience. First I want to give you a blowjob and have you cum in my mouth. Second and this is a bit more edgy or kinky depending on how you look at it. I want to be taken, somewhat forcefully."

Gary looked at her puzzled. "It's not that I didn't like last night, but I want to be used. I want you to bend me over a counter, table, or something, and shove your cock into me fuck me hard until you cum and then pull out and leave me. I know it sounds rough, but I really want to experience that primal lust. I understand if you don't want to do it." Marissa says.

"I will be happy to help you live out your fantasies. How about you fix us some coffee,"

"Sure," Marissa gets up and heads to the counter.

Slowly and quietly, Gary gets up and walks behind her. He grabs her, pushes her over the counter, rips her panties off, and shoves his cock into her. She screams as he thrusts into her struggling to get free, he has the advantage of size and position on her as he thrust hard and fast into her. She grunts, as his cock is pistoning in and out of her. If she had not been used so well, just a while before, he would be tearing her in two. He thrusts, "Take that cock you slut" he growls.

Thrusting harder and harder, her thighs slamming into the counter, he ravages her hole. No more than two minutes later, he slams into her for the last time as he sprays his load up into her. He pulls out, pulling his pants up and taking a seat back at the table. She lays bent over the counter cum leaking from her ass, and gently crying.

Lisa gets up putting her arm around her, she leans in, "what's wrong sweetheart? Isn't that what you wanted?"

Gently sobbing Marissa says "oh yes, it was."

"Then what's wrong?"

"I came while he used me, and I'm not sure why. It was so unlike last night and so impersonal. I can't understand why I feel this way." She straightens. "I'm going to shower." She walks out of the room, tears running down her face.

Gary starts to get up and Lisa motions him back down. "She needs some time to cope. Things are moving faster than she is able to process them right now." She pours them some coffee and they sit sipping, trying not to feel uncomfortable with the situation. After a while, Marissa had not returned, and when Gary got up to check on her Lisa did not stop her.

Marissa was standing in the shower just letting the water fall over her when Gary walked in. He did not say anything, just climbed into the shower behind her and began to caress her back. "Care to tell me what's wrong?" She does not look up, or jump, she just stands there. "I never meant to hurt you."

In a light whisper, Marissa responds, "I know. I don't know what to do or think right now. I am was so overcome with emotions after you made love to me last night, to be so used by you, and for me to ejaculate while you took me like that. I am not sure what to think. Things are so scrambled in my head right now."

"Shh sweetheart, did you enjoy it?"

For a minute, she did not answer. "God yes! It was wonderful! I mean I love my wife, and what she does with her dildos, but to have a man want me and to make love to me, it's such a different feeling. I want to experience it again and again, but I love my wife and never ever want to hurt her."

He leans over her back and whispers in her ear "How are we hurting her? She is the one who wanted you to experience this." He kisses her gently on the neck. "You are such a beautiful woman. I will make love to you as much or as little as you want."

He begins gently nibbling on her ear. She moans, his hands begin caressing her breasts and roaming her body. He works slowly down to her ass, gently kneading and cupping her firm round cheeks. He kneels behind her, spreads her ass, and begins licking her well-used hole. Slowly, gently he licks around the hole gently flicking and probing it. When she pushes back against him he enters her with his tongue, sliding it as far in as he can get, tasting himself in her. Then withdrawing he begins a slow gently tongue fucking of her hole.