The Reluctant Heterosexual

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Tanner finds his gay roommate adorable in drag.
6.9k words
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Authors Note: I wanted a writing challenge. So I picked the genre I was most unlikely to write a story for. This an experiment to see if I could put my mind into a character that I would most likely never become. Most of my stories are based on my experiences, this one is based mostly on my imagination. I hope if you're into gay stories that you enjoy it. If you're not, be advised this is a graphic gay (Bi) encounter. Thanks in advance.

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Thinking back on it, I still ask myself, 'Did I really do that?'

Let me explain. I owned a small house on the north side of Indianapolis, Indiana. Being young, I think I was 23 at the time, I took on a roommate to help me make ends meet. I knew that over a few years my income would rise to let me comfortably make my house payment, until then, leasing a room seemed to really make sense.

Chris was about the fourth person I interviewed. His credit checked out, he had excellent references, and best of all he was gainfully employed as a Database Administrator. I figured being a computer programmer that I could learn from Chris's expertise. We seemed to hit it off from the minute he moved in, after a week or two, it become obvious that Chris was gay, but hey, this was the 1990s right—no big deal.

If Chris had a boyfriend, he was really pretty discrete about it. Most of the people he invited to the house were girls. For a guy who was supposedly gay, he seemed to draw chicks like a magnet. Luckily for me, one of those women happened to be Jasmine. The olive skinned, dark haired girl and I hit it off from the day we met. She just happened to be really good friends with Chris.

At first, when Jasmine and I started seeing each other, I kept myself reserved. Not only did I like the girl, but I found myself really attracted to her physically. She seemed to exude sex appeal. She was 5'-7" to my 6'-0", and it was like her and I were made for each other.

On my third date with Jasmine, I was invited in to her apartment for a nightcap. After a drink or two, the two of us found ourselves in a tight embrace as I kissed the 19 year old girl passionately. Our hands seemed to roam everywhere as we explored each other's body. I don't think either of us had any doubt where all the kissing and caressing was leading.

Standing in the living room of her apartment, we slowly started helping each other out of our clothing. As Jasmine's pretty pink bra came off, my hand found its way up to caress and massage her shapely breasts. She had the most perky, dark brown nipples I'd ever seen. I couldn't help brushing their wonderful hardness with my finger tips. Before long I was lightly pinching them and giving them a gentle tug. Jasmine seemed to purr as I gave her magnificent breasts my attention.

After spending time kissing her neck, stroking her back and sides, moving ever so slowly downward. My mouth was rewarded when I took one her hard, protruding nipples between my lips. I gently suckled her as one of my hands massaged her other breasts. My other hand found its way inside the waist band of her panties and was kneading her delightfully soft cheeks of her butt.

I was rewarded for my attention with a quiet moan and a few delightful tremors that seemed to travel throughout her body.

Jasmine was busy herself. Not only was her hands stroking my skin, when I started to love her magnificent boobs with my mouth, her hand found its way inside my boxer shorts. She fondled my cock as my hand continued to explore her ass.

That's when I decided I wanted to taste the girl. So I began to kiss down her chest, around her diaphragm, and down onto her soft, firm tummy-as she like to call it. To facilitate my intensions, I encouraged Jasmine to lay out on the carpet. Once in place, I continued to explore her abdomen with my warm, wet kisses. I could faintly make out her musky scent wafting up from below.

Jasmine's body was shapely, she had large breasts without them being so big they were out of proportion. If I had to guess, she probably wore a 'C' cupped bra. To match her delightful breasts, she had a small tight waistline that curved out pleasantly into her shapely, rounded hips.

I kissed lower and Jasmine giggled. She said, "You know, in my heritage, what you're about to do it really taboo."

I chuckled, "What am I about to do?" She blushed and giggled.

With a little bit of concern, I asked, "You don't mind do you?"

Our eyes met-hers sparked, she bit her lower lip demurely, and she answered, "No, I want to see what it's like."

With that, I went back to kissing her tummy underneath her belly button.

I began to remove her panties slowly as my mouth followed the waistband down even further. My mouth grazed through her dark, tightly curled pubic hair. Jasmine let out a little gasp and trembled as my mouth moved over her mons.

I moved my body around, peeling off my boxers as I did. I wanted to be ready for action when the time came.

Jasmine raised her hips slightly, allowing me to pull her panties from beneath her butt. With one hand, I pulled them down past her knees as my mouth continued to explore her dark triangle. As soon as I had her panties off, she spread her legs slowly, allowing me to crawl up between her lovely, smooth, soft naked thighs.

I could feel a soft, warm thighs against each of my shoulder as my mouth found its way to her amazing pussy lips. I began to kiss her pussy lips like they were the lips on her mouth. Jasmine closed her eyes, her mouth hung open slightly and she repeatedly moaned as I began to explore her folds.

She had a delightful musky smell mixed with of all things, jasmine perfume. Apparently she had put a drop just above her pussy before our date. The scent was heady to say the least.

After kissing around her entire bottom for a bit, I moved my mouth to the center and started to explore her pretty brown labia. They were thick and fluffy, but didn't hang down like with some ladies. They made her pussy look plump and inviting. I ran my tongue up between the fluffy inner lips and began to taste the juices that had been gathering between her legs.

I moved to explore her opening, I ran my tongue up inside her vagina as far as I could. Once inside her, I started to undulate my tongue in an attempt to stimulate the numerous nerve endings that a lady usually has around the opening to their love canal. I certainly enjoyed the taste of her copious secretions that seemed to flow from inside her vagina.

After giving her a tongue fucking, which her writhing hips told me she totally enjoyed. I slipped a couple fingers up inside her honey pot, and I began to finger fuck the girl as I moved my mouth and tongue up through her lips, my destination was her puffy, swollen clitoris. I wanted to see how she tasted after she came.

I moved on her love button. I gently sucked it inside my mouth as I began to flick it with my tongue. Jasmine began to wriggle her hips as I felt shivers of delight course through her naked thighs. She moaned frequently, gasped occasionally, and whined constantly as her passion began to overwhelm her.

Knowing she was on the cusp of her orgasm, I increased the intensity I was applying to her clitoris, and at the same time, my fingers curled up behind her pubic bone and I began to massage her 'G' spot.

When Jasmine came, she did it in a big way. She nearly screamed as her passion released. She arched her back up and began thrashing her head from side to side. Her entire body was writhing in pleasure. Her thighs clamped against the side of my head over and over again.

I notice a flood of juices began to flow from her vagina, and I was down on top of it with my mouth, lapping up the flow with my tongue. Her nectar was sweet and wonderful and there was plenty to enjoy.

After enjoying her wonderful taste, I felt like it was time to move to the main event. This was confirmed when Jasmine, coming off her climax, asked, "Wow, was that ever nice! Fuck me Tanner, I need to feel you inside me." I didn't need to be asked twice.

I quickly crawled up the olive skinned girl, the head of my hard cock finding its way inside the lips of her pussy. I moaned out as the feeling of her hot, wet lips enveloped the head of my shaft. With great expectations, I adjusted myself with my hand, sliding my mushroom shaped head inside the opening to her vaginal canal. I pushed.

She was so delightfully wet, that I slid deep inside her tummy. I was quickly buried completely inside my lovely lady; our pubic bones were snuggly mashed together. She gasped out, "My gawd, Tanner, your stretching me out like you wouldn't believe, you fill me up completely." She whimpered and continued, "Fuck me Tanner. Fuck my pussy."

With my weight resting gently on her body, I began to cycle myself in and out of her hot, wet, tight vagina. I could feel her walls gliding over the skin on my hard shaft. It was a pure delight to be inside the girl, fucking her with a leisurely rhythm.

Breathily she gasped, "Wow, I love the way you fill me. You make me feel whole. The flange on you cock is lighting up the walls of my vagina like a Christmas tree." I learned that Jasmine loved to vocalize what she was feeling as she made love.

I continued to rock my hips up and down, causing my cock to piston inside Jasmine's canal. She was tight and silky causing the pressure up inside my bottom to climb. Before long, I was about to cum. Not knowing if she wanted me to pull out or what when I came—I wasn't wearing a condom, I announced, "Wow, um, ah, I'm about to cum!"

Jasmine purred, "Fill my pussy with your cum, Tanner. Spurt it all up inside me." I granted her wish.

As my cock began to throb, Jasmine seemed to enjoy it all. She whispered, "My gawd, I can feel you pulsing against my walls. It feel fucking fantastic!"

I held myself tightly against her bottom as I felt pulse after delightful pulse inside my cock. I know I was bathing the inside of her belly with my hot semen. Nothing between me and her cervix. That's when I began to hope that Jasmine was on birth control. I really liked the girl, but I wasn't ready to begin parenthood quite yet.

After what seemed like forever, my cock stopped throbbing. I had delivered my load inside the lovely dark haired girl. I gently slid my body off of her, and I pulled her into a tight embrace as we both enjoyed the afterglow of making love.

I spent the night, and we fucked throughout the early morning hours. Jasmine wanted to see if she could give me a blowjob, another taboo in her culture. Even so, she did a marvelous job given the fact she never attempted one before. Along with all the fucking, I ate her pussy several times all over again so I could taste more of her delightful cum when she had her orgasm.

The question is why am I telling you all this, it really has nothing to do with the main story I'm trying to convey. I guess I'm telling you so you will believe me when I tell you I'm entirely heterosexual. Something you may not believe after I tell you the rest of my tale.

It was Halloween. I dressed up like Dracula so I could greet all the little kids that came to my door. Chris, who was going to a partly later, dressed up like a woman. To be more precise, like a princess. Knowing Chris, I didn't find it entirely out of line with his character. What amazed me still to this day is how good he looked while he was in drag.

Chris in drag: if I was to see him out on the street, I would swear he was a nice looking young woman. He had a heart shaped face, and his eyes were set wide on his face. He had skillfully applied makeup and had on a shade of deep pink lipstick.

Chris normally wore his blond hair long, so he didn't need to wear a wig. He had his tresses done up in long curls at the side of his head instead of done up in his normal ponytail. He had a hair stylist as one of his many girl friends. Chris, a guy, looked like a woman who had just stepped out of a Jane Austin novel.

As young as he was, he was only 19, the same age as Jasmine, he didn't have much in the way of a beard, what he did have was closely shaved along with his armpits, which were visible when he raise his arms in the sleeveless dress he had on.

He didn't bother to stuff a bra. He had just enough shape to him to make him look like one of the boyish models that everyone seemed to enjoy in the fashion world. His hips had a natural feminine curve to them.

Why am I telling you all this. Well, I guess it's because I was finding myself attracted to my roommate. I knew he was a guy, but my eyes were telling me otherwise. If Chris and I had been in a bar, I'm sure he would have drawn the eyes of every lounge lizard and bar troll in the place.

Chris helped me give out candy. A young girl commented, "I like you're wife's princess costume, she's pretty." So, you see, I wasn't the only one. At 8:00pm, Chris and I turned off the porch light. Chris was heading for his party.

I don't know if he was being polite, or what, but Chris invited, "Hey, Tanner, why don't you come along. There are going to be a lot of straight ladies attending. I know most of them, and they are the kind of girls I'm sure you wouldn't mind meeting."

I said, "Hey, you know that Jasmine and I are dating."

He giggled charmingly, and in his feminine way he chided, "I wasn't suggesting you fuck them all. I just know how much you enjoy the company of nice looking girls. Most of them are between 19 and 21. I think you'll have a great time. Come on Tanner. You don't want to hang around the house all evening by yourself, do you?"

I gave in. I asked, "Is my costume okay?"

To my amusement, Chris said, "Hey, you look hot! I'm sure the girls will be all over you. I certainly think you look sexy." I didn't think anything of his comment. He had said things like that before, he meant nothing more than a compliment.

So Chris and I headed for the car to head to the party.

I decided to drive knowing that Chris liked to drink more than me. I was a sipper. I nursed a drink over long periods of time, keeping myself delightfully tipsy without becoming drunk. Chris was happy to just ride along. I was astounded with myself when I absent mindedly opened the passenger door for Chris so he could get seated. Alarm bells started to ring when the younger man looked up at me through his curls in an appraising manor.

The party was a lot of fun, just like Chris had said it would be. I found myself having delightful conversations with not only the girls in attendance, but several of the guys too, knowing that at least half of them were gay. Gay or not, they were marvelous conversationalists. I found myself sort of disappointed when people started saying their goodbyes, and the party began to wind down.

Just a little after one in the morning, I found myself opening the car door again for my roommate. It seemed like I kept forgetting that Chris was a guy. Honestly, I knew it, but my instincts were behaving in opposition to my knowledge.

When we got home, I could tell Chris was feeling good, but he wasn't noticeably drunk. Again, I opened the car door for the guy. Somehow I seemed to be wishing he was the delightful creature he appeared to be. As he climbed out of the car, he snugged his chest up against my arm. Had he been a woman, his breasts would have been pressed into my arm.

I was set back a bit when Chris reached out with his hand and took one of mine. He pulled me towards the house and said, "Why don't we get inside." I let him continue to hold my hand as he pulled me towards the front door.

To say my emotions were conflicted would have been an understatement. I was actually letting a guy hold my hand-a guy who looked like a princess—he was still a guy. Once inside, Chris turned on some soft music and reached into the refrigerator as he brought out a half drank bottle of wine. He quietly poured two glasses and brought on to me. After I took mine, Chris held up his glass and said, "To a wonderful party." I raised my glass and then took a sip.

Chris looked at me and chuckled, he shocked me when he said, "You know, I've been watching you check me out all evening. You know, that's really flattering Tanner. I've always thought I should have been born a woman, your sneak peeks seem to validate it."

He smile when I blushed. He said, "Hey, don't worry about it." Then he caused me to almost drop my glass when he asked, "This is a nice song, would you like to dance?"

I stammered, "Um, Chris..."

He chuckled sexily, "Hey, all you need to do is pretend I'm the pretty woman that you think I look like. Tonight, you dance with a princess."

More than stunned with my actions, I reached out and took Chris into my arms and we began to glide around the room, dancing to the soft music. Taking his advice, I tried to forget that Chris was a guy—somehow it worked. I found myself dancing with a delightful young woman.

The next song to play was a slow, rhythmic love song. Chris snugged up against my chest and I found myself pulling him tight against me as we rocked slowly back and forth to the music. Chris cooed as my hands moved down to rest on his lower back, almost on top of his shapely butt.

After a minute or two, Chris looked up at me longingly, expectantly, obviously wanting me to kiss him. Lost in the moment, I move my lips to his glossy, pink lips. I gently kissed him.

Chris hungrily started to kiss me back. Amazingly, as I began to kiss the young guy, I felt my cock begin to twitch. I was getting aroused kissing a guy! Okay, he looked like a princess, but he was a guy!

Something snapped inside my head, I told myself, 'Just go with it, Tanner.' I was enjoying dancing, I was enjoying kissing Chris; I didn't know where this would all end up, but for the moment, I was willing to try things.

After a bit of tender kissing, it started to become passionate. I stiffened just a little when Chris slipped his tongue between my lips, but soon I felt myself relax and I move my own tongue to greet his. To me, it seemed like I was kissing an attractive woman.

When Chris started to unbutton my formal button up shirt, I almost pulled back and put a stop to what was happening. Almost.

The entire time we were kissing passionately, our hands were stroking each other. Chris broke the kiss eventually and started kissing my neck. Almost the same way I would kiss Jasmine's. Chris kept kissing down until he moved his mouth to my nipples.

I didn't realize how nice it felt to have someone suck on my breasts. I'm a guy; it's not supposed to feel good to a guy, right? Especially when it's another guy doing it. But, it did; it felt really nice. Having his hot, wet lips forming a seal around my smallish nipples, having him run his tongue around them, felt wonderful.

Then I felt his hand move down as he slowly unbuckled my belt, then he unclasped my slacks, followed by him slowly pulling down my zipper. With my pants loose, they fell down my legs. I was appalled, yet I was so intrigued. I didn't do a thing to stop him. My cock began to grow in anticipation of his touch.

I felt his smaller warm hand reach inside my boxers. He grasped my hardening shaft; for the first time it was being fondled by a male. Again, my intellect was telling me a man had a hold of my cock, my perception said I was being fondled by a woman. As I decided earlier, I just decided to go with it.

I felt myself enjoying the attention Chris's mouth was giving my nipples at the same time his hand was stroking my hard shaft. When he started to kiss down my chest, I had to make a decision. I knew what Chris wanted to do, but was I willing to let him do it? Eventually, to my astonishment, I decided I would let him.

I felt him plant kisses all over my body, on my ribs, around my diaphragm, and down onto my belly. He even stuck his tongue inside my belly button and reamed it. These were all things I did to a woman to whom I was making love to, and now it was being done to me. I would be lying if I told you I didn't enjoy it.

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