Living in a small small town in rural New York, housing is often at a premium. Not something I thought about much, but until fuel prices went up.
As soon as the gas prices started to skyrocket I realize I would probably have to sell the house, until I looked at the real estate ads and saw a couple ads from students looking to rent. My first thought was to find a young co-ed to stay in the one of the three bedrooms of my house. Like many middle-age men I fantasize about young girls with there bare midriffs and hips.
My house had three bedrooms: the one I used; another that I used mostly for storage; and the guest room. I harbored some thought to cleaning out the second room and getting two roommates. The problem was I couldn't bare going through what was stored in the room -- my wife's belongings.
I have been a lone for a couple years, since my wife died in a car accident. It had been such a shock, I just packed all her things and put them in the bedroom. I didn't want to stir up the memories. I often thought of taking it all to the thrift store, but two reasons kept me from doing that. The first was I did want to keep a few things, some photos and items that I knew some day would not be painful to look at. The second reason was that because I lived in a small town I knew I would see many of the items worn by others.
My wife had been a petite woman and the clothes would have likely have been adopted by young women, the same women I fantasized about being my new roommates. It was an irony, but life is filled with ironies.
Though I had dated a few several women, my sex life had been somewhat limited. While the chance of a 20 year old woman wanting to sleep with a man that qualifies for senior discount were as slim as the thongs the women wear, it didn't stop me from thinking about it. The dream was short lived.
There were four ads, only one was from a woman and had already found a place when I called. I called the other three and interviewed them during the following week. It was an easy choice. The two that were in the forestry program were out and the culinary student moved in a week later.
It was a decision based on physical demeanor. The first two were big strapping guys that talked of drinking and women -- two things I enjoy. Regardless of what I enjoyed, I did not want to turn my place into a frat house. Stephen on the other hand was slight, almost effeminate 19 year old student. Stephen also seemed the most desperate for a place to stay in, and I thought he would be less likely to do anything that might compromise a place to stay.
Part of the desperation was Stephen's limited means. I had planned to charge $500 a month, plus a deposit. Dependent on his student loan -- that had not been released by the bursar's office yet -- he could only pay the first month's rent. He seemed trustworthy enough.
Stephen turned out to be an excellent roommate. He was very quiet and neat. He was much more cleaner than I was and took on a few household chores for me in exchange for half of the rent. Not only did he keep the house clean, he was a natural cook. Eventually I started calling him Stephi, instead of Stephen.
He could have worked in most restaurants in town, but he chose to work at a diner -- serving up breakfast. He did, leaving his afternoons and evenings for school. Since his classes were in the afternoon, he was home at 5 p.m. each day and began making dinner; usually some exotic dish that he had learned about in one of his classes.
He seemed to not care about a social life. He certainly embraced his studies. I thought that he might have been a bit of a wallflower. Still he was young and I wondered why he didn't want to seek out some female companionship. I wouldn't say he was handsome, he was more pretty. The kind of qualities that would be ridiculed by guys his age, but I knew a few girls must have found him attractive.
Even if there weren't any young women that found him attractive, from time to time -- as I masturbated -- my mind drifted to him. At first I resisted the image, but after a while I found a quick path to an orgasm by imagining him licking my balls while he worked my shaft. Or another fantasy involved him offering his hips to me, begging me to exchange this months rent for sodomy.
These fantasies came easily, because of Stephi's fair and comely looks. His heritage was Scandinavian. When he work shorts it looked like he had shaved his legs, because the hair on his legs was blond and thin. Stephi had a penchant for wearing flannel pajama bottoms around the house. The bottoms had been tight in August when he moved in and now after several washings had shrunk and clinked to his round hips. So tight I knew he work no underwear.
I tried not to look, as to not be caught staring at his package, but I was drawn to his crotch. As feminine as the rest of Stephi's body was, his package was like something out of a porno movie. While not enormous, it was prominent.
I knew much of the allure was Stephi's youth, just as a fantasized about young co-eds, the though that I could seduce a 19 year old man was exciting. I am not sure what Stephi thought of me, I assumed he felt I was just a old man or a father figure of some sort.
We spoke, but seldom about anything sexual. Mostly I talked to him about school and various professors. Living in a small town I knew most of the people who taught his classes. I worked at an arts center and had dealt with a couple of the professors who catered our events. Stephi was a very good mimic and often would tell me stories adding little nuances that would make me laugh. He had acted in high school and was a pretty good performer.
Late October he came home and caught me me off-guard. I had a weekday off, because of a gallery opening scheduled for the next Saturday. I took advantage of being alone and was masturbating. When Stephi knocked on my bedroom door, it was unexpected. I threw on a robe and opened the door. I instantly was on edge. Right after imagining Stephi bobbing his head on my cock, it was uncomfortable to be face to face with him.
I looked back, wondering if this was one of those moments where I open my robe and he would provide oral satisfaction or if I might end up as a headline in a a sexual assault case. It must have been noticeable because he kept apologizing and said he could come back later. I thought it was better to talk now, in spite how I felt I was riding a sexual tilt-a-whirl.
He started telling me about how his boss had asked the employees to dress up. Why he was telling me this didn't make much sense and totally confused me until he brought up the clothing in the spare bedroom. For some reason I thought he wanted to empty out the room. Then he explained he had thought of wearing something. He said he had been cleaning in there and noticed the women's clothing and since he had to dress up he wanted to dress as a waitress. Caught off guard I told him, "sure."
He looked at me a moment, then left. I took a shower to finish what I had started. It was a good thing too. Fifteen minutes and one cold shower later I had cleaned up and went downstairs, half expecting to have lunch prepared by Stephi. I had tossed on a pair of flannel p.j. bottoms and a sweat shirt. I couldn't find him anywhere downstairs and wondered if he had taken off to school; then I heard him upstairs.
The way my house laid out was two bedrooms and a bathroom upstairs, with another bathroom and a bathroom down. There was my room upstairs and the other was the room -- containing my wife's belongings. I was intrigued at what Stephi was doing. I tiptoed upstairs and door was ajar. Through door crack I saw him trying on clothes -- my wife's clothes. He had on a blue dress.
The fact that I was spooked had little to do with Halloween being around the corner. Not only did he have on one of my wife's sexiest dresses, he had on a pair of spike heels and a blue wig. The wig and heels were not my wife's, but added to the look. He was looking at himself in the full length mirror.
I noticed two things right away: Stephi was filling out the dress quite well and the 10 minuted cold shower wasn't working. He was turning and looking at the outfit from different angles. Then he pulled the dress over his head, standing in front of the mirror in only heels and a jock and the wig. His ass was smooth, white and shapely. That was accentuated when he bent over to grab another dress. He brought it up to put on, but struggled with it. It was then I noticed in the mirror his 'package.' It was not what I expected from the slight boy. With Stephi blinded by the dress over his head, I push the door open a little more to see.
The dress was white with purple polka dots. After a couple tugs he got it down. It was maybe a half size too small and clung to his hips. I was admiring the curves of his haunches when I realized he had stopped moving and was looking back -- through the mirror -- at me.
"Like what you see?" he asked.
The question was not flirty, but more Stephi seeking my opinion.
"Um...yes," I stumbled.
"I was even thinking of going out at night, with a different dress," he said, excited. "Unless you don't want me to."
"No, I can hand out the candy by myself," I said, feeling like an idiot. "I mean, I don't know what I mean."
He came closer, "something wrong?" He pulled the door open and I could see several dresses piled next to the mirror.
"It's not, I don't know...well I thought it was the," I was trying to say two things at once. I wanted to comment about what a queer feeling it was to see him in my wife's clothes and how REALLY queer I was feeling. I wanted to throw him down and take him right then and there.
"I'm sorry about the mess."
"No, it's not the mess...I know how well you will clean up," I joked. "I'm just well a little surprised how good you look. Sexy."
He was about a foot away from me and just stared at me...I couldn't believe how soft his blue eyes look with the wig and purple highlighting them. I was trembling.
I pressed my lips together, then let them slightly part.
He leaned into me. To kiss me.
I inhaled, expanding my lungs.
Just as his lips were to touch me, I turned my head. I wanted him, but I didn't know how to respond to desire for a man. Stephi's face nuzzled my neck.
"I..I I," I wanted to apologize for turning away, but I owned no words.
Stephi bent down, kneeling before me. On his way down his hands caressed me. His fingers slipped into the elastic of my bottoms. He pulled down the pajamas, taking my boxers with them. My erect penis twitched when his tongue slide from the tip to my balls. Even without his touch I had been close to a climax; now I could only lean against the door jam and sigh.
I felt nothing.
Then his fingers fondling my balls. The moment was filled with the sound of air rushing to my lungs, then a moan when his mouth engulfed me. He had seen my hesitation and perhaps was afraid I would stop. Or maybe he was nervous. Or excited. Either way he was working me and working me fast.
I grabbed his head, the wig, and held on. Unconsciously I started to thrust, pulling at his head.
"Ahhhhhh," flowed out of me with out me realizing it. And I was cumming.
Stephi worked me, until I couldn't take it.
My cock is hyper-sensitive after an orgasm.
I pushed him back.
The wig had come off. His blond hair was damp with sweat and messed up.
I freaked out.
Looking down at him I realized I had just received oral from a man.
A MAN.
Stephi was effeminate, but looking down on him smiling, with a little sperm on his chin, there was no doubt this was a man who brought me to this frenzy. I stepped back, a little afraid of what had happened.
Stephi was smart. He was hurt by my reaction.
He turned and ran down the stairs. If he heard me call, he ignored me. I stood at the top of the stairs. I heard dashing around downstairs. Then his bedroom door slammed, followed by the front door.
Was it possible he would not return....
To be continued