The Roommate
by Anita Wiener
I've been rooming with Bob for two years now. He and I met about 5 years back, while we both worked at the grocery store to get through college. We were good friends from the moment we met. We had similar interests, were both outgoing, good looking, and hated working at the grocery store.
He and I have gone through many girlfriends over the years. I even came perilously close to marriage at one point. Through it all, he and I have always remained best friends, double dating, surfing, and going out.
About two years ago, it so happened that each of was re-locating, so we decided to shack up together. We found a great deal on a flat on Russian Hill in the City. It's really worked out well. Being friends doesn't always lend itself to being roommates, but he and I have proven to be very compatible.
About two months ago, Bob started to seem to be getting more and more distant. I figured it probably had something to do with his new girlfriend. This wasn't the first time that we drifted apart due to girlfriends. But this was a little different. Not only was he home less, but even when he was home, things weren't the same. He hid out in his room a lot. He wouldn't hang out with me and just watch TV or anything. I never confronted him about it, I just gave him his space.
Another thing I noticed was that Bob was decidedly less aggressive, in both his appearance and manner. He used to be very outgoing and brash, almost obnoxiously so. But not lately. He has been avoiding looking me in the eyes, and he never raises his voice. Since he was avoiding me, I never really got the chance to ask him what was up.
Anyway, that would have been OK, except that it seemed to get worse. My first reaction was just that he must be depressed and keeping a low profile until it passed. But that wasn't it. He began to dress differently. To carry himself differently. He wasn't the macho guy anymore. He looked like some art student or something. His normally short crew cut was growing into shoulder length hair. And he was wearing softer clothing, trading his plaid shirts and T-shirts for silk shirts. He was definitely changing.
The really frustrating thing for me was to be cut out of the loop. He wasn't talking to me. A month ago, I had had enough and I confronted him. He came home with some shopping bags, grunted a hello, and then went straight to his bedroom. A minute later, I went to his room and knocked on it.
"Bob. Hey, what's up? Can I come in?" I asked.
"Hey Geoff. One sec."
I heard some ruffling going on, then the door opened slowly. "Hey buddy. I just wanted to check in with you. It's been a while and, y'know, I want to see what's the latest." I kind of pushed my way into his room as I was talking and he backed behind the door.
The first thing I noticed was that his room looked different. He had redecorated it. It looked frilly and soft, with muted colors. The Pearl Jam posters were gone. I took a seat on his white lace bed spread and turned to face him as he continued to stand by the door. His body language looked like he was eager for me to leave.
"Well. Yeah. It has been a while. What have you been up to?" Bob asked.
"Me? Nothing much. I've just been wondering about you. You seem different. I wanted to make sure you are OK." He didn't look OK. Or, I mean, not like Bob OK. I think he was wearing some mascara and his hair was teased up into a softer looking style. He might have looked OK if you were looking at somebody else. But he wasn't the Bob I knew. "You still seeing Carol?"
"Carol? Yes. She's great. We're seeing a lot of each other. In fact, I was just with her... shopping." His eyes darted over to a shopping bag on the floor. Frederick's of Hollywood.
That piqued my interest right away. "Frederick's eh? You two getting creative?" And I made a move over to the bag to see what was in it.
Bob dashed over to pick it up and held it in his hands, preventing me from getting into it. "Well, you know girls. Always have to buy them something pretty."
"Yes I know. But why do you have the bag, and not Carol?" I asked.
He paused a moment, then responded "She accidentally left it in my car. I'll give it to her next time I see her."
"Speaking of Carol," I asked, "when do I get to meet her? Sounds like you are really hitting it off." Bob didn't respond directly, and seemed evasive, so I tried another question. "I notice that you are dressing different. No more tennis shoes and jeans. What's up there?"
"You know how girls always try to makeover a guy. She's been taking me shopping and stuff. That's all."
Seemed reasonable to me, so I didn't push it. But as he spoke, it was clear to me that he really seemed different and not the same old Bob. It wasn't just the clothes. It was Bob. "Well, anyway. I just wanted to see how you were doing, make sure you were OK. You know I care about you, and that you can always talk to me if there is something on your mind..."
"Oh. Thanks. I know you do, and I appreciate it."
With that, he ushered me out of the room and I noticed his nails for the first time. They were longer, and painted white. As the door closed behind me, I just shrugged and figured he must really be under the influence of this Carol chick.
Another 3 weeks went by, and I hardly saw him at all. He was even more evasive than before. From the glimpses I caught of him, things hadn't changed. He was still dressing like a hairdresser or wedding planner or something. It was his life, so I didn't push it, but it was getting increasingly difficult having him as a roommate. Normally, he and I would share groceries or talk about the bills and rent. Lately, none of that was happening. I would have to leave him notes on the kitchen table.
A few nights ago, I came home early from the baseball game. It had been rained out. As I was approaching the steps to our flat, I saw a woman coming out. Or, I thought it was a woman. She was wearing a short blue minidress with matching purse, white pumps, seamed stockings, and looked pretty glam. I was naturally very curious who was coming from our building. If it was a new tenant, I naturally wanted to meet her.
When she looked up and saw me, she froze. So did I. It was Bob. He was barely recognizable. I really thought he was a woman, but I knew that face. I was speechless. I just kind of stood there waiting for something to come out of my mouth. Nothing ever did.
Bob turned his head back down, and turned down the street, walking away from me. Even from behind, he looked like a woman. He walked in those shoes like he knew what he was doing, shaking his ass to and fro as he walked.
I was left standing there. I watched him as he walked the distance of the block, and then turned out of sight. Bob? I didn't know what to think. I headed up to the flat, went in, popped open a beer and plopped on the couch. I tried to make excuses for him. "Maybe it's a costume party." But I knew that it wasn't a one-time thing. I had been so stupid. Why hadn't I seen it? He had been showing all kinds of obvious signs, but I didn't recognize them. I wondered if he was gay.
Now that was a thought. He and I had been roommates for two years, and best friends for five. I would think I would know something as major as that. He had never shown any signs. And he was always dating and going out to the bars with me. No way. He was definitely straight. That may have changed now, but he definitely used to be straight.
I needed answers. I was just guessing about all of it. I needed him to tell me what was going on. He had avoided me through the last two months, obviously not wanting my friendship or ear. I needed to know where we stood. If we were still friends. I decided to wait up for him.
And I did wait. He didn't come home until 4am. The door slowly creaked open. Before he could dash off to his room, I got up and intercepted him at the door.
"Bob, we need to talk." He looked up at me and I couldn't believe my eyes. He was a very convincing woman. But I wasn't fooled, He was still Bob underneath.
He replied "I know. Let me get a drink. Can I get you one too?" His voice was so natural, coming from a woman's visage.
I answered yes, and he went off into the kitchen. I watched him walk away and was amazed at how the dress fit him. He had a tiny waist and larger than normal hips. And his legs looked great in those pumps! Really, if I didn't know better, even under the lights, I would have mistaken Bob for a woman... a good looking woman. I went into the living room and took a seat on the couch and turned off the TV.
Bob began talking to me from the kitchen while rattling some bottles around. "I guess this conversation has been a long time coming." I couldn't see him, except for the shadow on the kitchen floor. "First off, let me apologize to you. I really should have told you sooner. You shouldn't have had to find out by seeing me on the street." He entered the living room holding two drinks, then sat down on the couch next to me, handing me my drink. "Salud!"
I joined Bob in the toast and took a sip from the drink. I began to see mannerisms that I had never seen before in Bob. The way he held the drink, and the way he took a sip. It all looked so feminine and pretty. He shook his head, fluffing his hair and stared me right in the eyes.
"I'm sure you have a lot of questions for me. I will answer them all. But first let me say that I'm glad it's all out in the open. I was kind of freaked out when you saw me, but now I feel relieved. I can finally tell you what is going on in my life." He set his drink down and crossed his legs.
Bob was sitting next to me, and I noticed cleavage peeking out from the top of the dress. How was that possible? "Bob, what..." I didn't know what to ask. Luckily Bob interrupted me.
"First off Geoff, you are going to have to stop calling me Bob. I've changed my name to Jasmine. And you will have to get used to seeing me like this and referring to me with female pronouns."
This was stunning news to my ears! Bob wasn't just dressing up. He wanted to become a woman. And I had to say that he was pretty successful. I could smell her perfume as her small hands, decorated with a few simple rings, reached out and placed a hand on my thigh. I could really see Bob as a woman.
"Do you think you can handle that?" She continued to look me straight in the eye and I grew increasingly nervous and confused about my feelings.
"I'm not sure yet." I took a gulp from my drink. I had expected to sit down here with Bob, and get the scoop on the situation. But here I was on the couch, in close proximity to a beautiful woman named Jasmine, drinking and making eye contact as her hand was on my thigh. My body was responding in a way that my mind found most inappropriate... It was getting a hard on. "But Bob, why are you doing this? Is it because of your girlfriend, Carol?" I asked.
"Jasmine!" she reprimanded, and play slapped me on the leg. She seemed kind of flirtatious and coy. "Yes. Carol has assisted me in my transition. But I have transitioned willingly. You will see. This path I am taking is wonderful, and has brought me here. This can't be a mistake can it?" She opened her arms, asking if she could be a mistake.
I found myself referring to her in the feminine gender. She was a woman, not Bob. Not male anymore. I was very confused by it, and ran toward the idea that she was a woman. It made my hard-on easier to comprehend. "No, Jasmine," I paused as the new name came out of my mouth, listening to myself, "you look terrific. Really. But how did you do it? And... I mean... Do you have..." I wanted to ask her if she still had a dick in there.
"Geoff! I'm surprised at you! A girl can't give away all her secrets can she? Some things are better left to be discovered."
Bob/Jasmine had moved in closer to me, and I was really torn. Part of me wanted to run out of the room, not able to accept that my friend, Bob, was kind of coming on to me. The other part of me wanted to pick up on this Jasmine woman and do her right there on the couch. She was leaning into me and kept her hand on my thigh when she took a sip from her drink and peered at me over the rim of the glass. She squeezed my thigh as she winked at me. That was the turning point for me. I wanted the person next to me to be Jasmine. It wasn't Bob. It was a beautiful woman who was definitely flirting with me. I gulped down the last of my drink.
"I really am relieved that you know the truth." She sighed and rested her head on my shoulder. I could feel her hair on my neck and her breath, warm and sweet, tickling my skin. "You and I have always been so close. I don't want that to change. Ever." She turned her face toward me as I continued to stare down at my empty drink. "Do you think we can remain close?" Her lips were practically on my ear as she whispered to me. A shiver ran down my spine and my cock was pressing at the seams of my pants.
"Well, I'm willing to try. It'll take some getting used to you, having... a woman around the house." I was so embarrassed that I found myself talking to my drink in my lap. With her other hand, she began playing with my hair.
"Well Geoff," her lips were touching the bare skin of my shoulder where it peeked out of my T-shirt as she spoke, "You know I really care about you. I want what is best for you." Her hand was no longer resting on my thigh, it was rubbing my thigh. And her lips were now rubbing up toward my neck in small silent kisses.
I felt kind of stupid just sitting there, but I didn't know what to do. I was incredibly turned on by Jasmine, and confused about Bob. I knew which side was going to win. Jasmine has made it more than obvious what she wanted, and I wasn't going to stop her.
"That feels good." I ventured.
"I've known you long enough to know exactly what pleases you." Then she bit into my neck and began to work her hand into my crotch. I was dizzy from the pleasure. She knew exactly how to drive me wild. I found myself moaning out loud as she pushed me back on the couch and mounted me. As she lay there on top of me she said "I love you Geoff." Then she came in closer and we kissed a deep passionate kiss.
I brought my hands to her hips and began to feel her feminine curves and pull her close as we continued to kiss. The warmth of the embrace floored me. I felt like I had known Jasmine all along and we were engaging in a long awaited release of mutual desire. Love.
Within minutes, Jasmine had removed my clothing. I laid there trying to catch my breath on the couch as she began to strip in front of me. She began to slowly take her dress up over her head, first revealing the tops of her stockings, then garters. I loved the way her pale skin peeked out over her stockings. Her dress moved higher revealing a pair of thong panties. Part of me was relieved that I couldn't see a cock, but the other part knew it wouldn't matter. As her dress came over her head, she stood there in her black lingerie eyeing me hungrily. Then she took her hands behind her back to release her bra straps. With a snap, the bra was released and fell from her body revealing beautiful breasts. They hung on her body body beautifully, forming perfectly shaped cups, just enough for a handful. I wanted to hold them. To feel their weight.
She brought herself back down on me and my cock rubbed against her soft belly as we began kissing softly. I was mesmerized by the feel of her body against mine. Her tits pressed into me and I grabbed the back of her head to pull her close. Jasmine made it clear that she was in control and began to work her kisses all over my body, eventually working her way down to my groin. I laid back and shivered with delight and she tickled my senses.
"Oooohhh..." She moaned as she got to my cock. "You are a big boy." Then she raised an eyebrow and grinned devilishly as she took my cock into her mouth. She was so warm, wet and perfect, that I almost came immediately. Apparently she could tell, and she pulled off of me and then went down to my balls and took both of them in her mouth. She worked them for over a minute as I groaned loudly with pleasure. Then she began to work the whole area with her tongue. I never knew the skin down there was so sensitive.
Then she began to work my anus with her tongue. It was fantastic! I had never known such delight. Her tongue swirled around, tickling my opening, and occasionally poking inward. I loved it. I began to see this region of my body as part of my sexual organs. It felt like she was fucking me with her tongue. Then she slipped a finger easily into my hole and continued to lick around it as she felt me up inside. It felt so good, I almost screamed. She began to work her finger in and out as she sucked my balls. I could do this all night, I thought.
Then, before I knew what was happening, I had my legs on her shoulders and she was bringing her body up toward mine. I saw her face, that beautiful face. The face I loved. And I needed to kiss her. To bring her toward me. I reached out for her face and brought her towards me when I felt her cock press up against my anus. I guess that answered my question about whether she still had it or not.
Still possessed by a burning desire to kiss her, I tried to bring her closer. With each inch, she pressed into me, her cock pressing harder for entry. With her face only an inch to go, I reached desperately for her lips as her cock tore into me. Our lips met just as I was ripped wide open. We kissed and squeezed each other desperately as I tried to keep from screaming from the burning pain. She felt so good against me, her body and mine locked in a sexual embrace, that I felt I could endure any pain just to be with her.
She began to rotate her hips, moving her cock inside of me gently. Slowly the pain turned into pleasure. With each kiss, with each breath, I began to enjoy the pain of her cock in me. Her hips began to move her cock in and out of me, eventually working into vigorous thrusts that pounded into me. I was letting out little yelps of pain mixed with pleasure with each of her strokes. I could feel her balls slapping against my ass as she continued to work her cock into my ass over and over again.
My own cock was oozing precum all over my belly. As Jasmine began to get into a rhythm our bodies became locked in a tight embrace. I was working my cock into her stomach, fucking her belly. I matched Jasmine's strokes and our cocks were thrusting in unison. It felt too good to hold it any longer. I was going to come. Nothing could stop me. I stared at Jasmine's beautiful face trying to capture the moment forever, wanting to savor the moment. Then I came in an explosion of cum. I was seeing stars as the whole world started to spin. I could feel my jism pressing into our tightly clenched bodies, lubricating our movements. I felt my anus clench down on Jasmine's cock, stopping her completely. She screamed. We both screamed animal lust and pain.
I felt Jasmine's cock pulsating inside of me. With her last scream, it burst into me sending gobs of semen deep within me. A seemingly endless series of pulses of her cock sent me deep into 7th heaven. I was lost in the pleasure as she collapsed on top of me.
Later that year, Jasmine and I got married. It was, to all appearances, a lesbian wedding. We both wore white. Jasmine had Carol as her maid of honor.