Well, I have no one to blame but myself, I suppose. Love and lust make us all do some pretty strange things, sometimes, but I never thought that I’d be looking forward to…wait! Let me tell you this story from the beginning.
I had wanted Gina for as long as I can remember. She was just so cool, calm & collected. A strong woman, and so aloof at times that it maddened me.
I met her when I was doing some odd jobs for her neighbor. I’m a handyman by trade, and Gina happened to be there when I was fixing this lady’s little plumbing problem. We kind of hit it off, I thought, but she didn’t give me any sign that she wanted anything more than good conversation.
Eventually, of course, I did some work for Gina. Later that summer I spent a lot of time working around her house, and she always seemed to find more for me to do. It was nice to have the work, and even nicer to be around her. We found that we had similar tastes in music and books and movies, and shared some great meals together that she whipped up for lunch while I was working there. Still, I never found that “in” that I was looking for, that little hint of an entryway into her more private self.
Whenever she was around me, she was dressed most casually, as she always had some project of her own going on, like building a bird house or messing with the innumerable animals she had on her property. Yet, through the sweats and t-shirts I could see that she had a really killer body, one that I’d give almost anything to explore. Her swaying breasts and round ass called out to me whether I was with her or not. She was really that deep into my brain. She’d just pop into my thoughts at the oddest times, and I knew I needed to know her better. Much better.
I putzed around her for years, finding myself surprized at my shyness. Usually, I’d make a move on someone early on, and take it from there if she responded. Something about Gina was different, though. I could make one of my outrageous comments, and she’d smile the smallest of smiles and ignore my bold advance as if I hadn’t said it, yet not entirely push me away. It was driving me crazy. It wasn’t just the physical attraction, although that was most definitely there. She is a bit of a looker. Not a model type, but those never attracted me. She is tall, sort of pear shaped, with a luscious ass I want to sink my teeth (and cock!) into. She’s not young, either, around 50, I’d guess, but she looks younger. Her hair is graying, but it used to be blonde, and it looks good on her. There is some sort of attraction to her that goes far beyond the mere physical, though, and I’ve wanted to explore that for as long as I’ve known her.
I’d been dropping in on her for short visits a lot, in hopes of finding that turn of phrase or whatever that would so the trick. I felt like some helplessly tongue-tied teenager, and at my age that seemed ridiculous to me, but I couldn’t quite figure out how to get through to her.
One time I went over, there was this guy there. He was what we’d have called in high school a “flaming faggot” type. Very outlandish expressions, everything blown out of proportion, he actually giggled a time ot two. His presense surprized me. I’d not have figured Gina to have friends like this guy. He was amusing, though, and I found myself laughing a lot around him. We sat and talked together for about an hour and a half.
The phone rang, and Gina took it into the bedroom to talk, and left me there with Tim.
“You really like her, don’t you,” Tim asked.
“Well, yeah. What’s not to like?”
“She likes to watch, you know,” he almost whispered as he grinned suggestively at me.
“I think she’s really hoping that we two hit it off,” he said, while looking me up and down.
I was stunned, and I’m sure it showed. I didn’t respond, and thankfully, I didn’t have to, as Gina returned to the room and returned her cordless phone to its little cradle.
I felt as if I was made of wood as the conversation resumed where it had left off. My mind was racing, trying to keep up as it considered this new piece of information. I had no center, anymore, no point of reference to deal with this.
Finally, Tim rose to leave. He kissed Gina on the cheek, and when I extended my hand, he shook it with his fingers stroking my palm. I am sure I blushed as he took his leave.
“What did you think of Tim, Sam,” Gina’s eyes bored into mine.
“Nice guy. Kind of weird, but likeable.”
“You think so? He’s weird?” She looked disappointed in my assessment.
“Not weird, maybe, but I think he’s gay.”
Gina let out a loud laugh.
“Of course he’s gay! Is that so weird?”
“Well, I haven’t been around too many people like that, so I suppose I’m the wrong man to ask that question,” I was back-pedalling poorly, but I had no clue what to expect after his little announcement.
“Did he come on to you, Sam? Is that what’s bothering you?”
I chuckled nervously.
“Well, I felt a bit like prey, the way he kept looking me over.”
“Kind of like the way you look at me, you mean?”
I was blushing again as she continued. I could feel the heat rising to my cheeks.
“I see the way you look at me, Sam. I know what you want, for the most part. Do you know what I want?”
Her eyes were again boring into my soul, looking for honesty, so I gave it to her as best I could.
“I have no idea what you want, Gina. That’s why I haven’t been…” I trailed off, not willing to admit that I hadn’t been successful with her.
“Haven’t been what, Sam?”
“I guess I’m trying to say that I don’t know what you want from a guy, so I don’t know how to really get together with you, Gina,” I fumbled about for the right words, wanting to express this all so very much better than this. It was out there, though, those words hanging in space, waiting for her response, expecting her rebuff.
She sat very still for a full two minutes. I didn’t dare to speak as her eyes never left my own.
“What did Tim say to you, Sam?”
“I shouldn’t repeat it. I wouldn’t want you to get mad at him if I quoted him wrong or something, or if I misunderstood him.”
Gina smiled, leaned back a bit, her eyes rolled to the ceiling.
“You are such a diplomat, Sam! You know damned well that you didn’t ‘misunderstand’ him! C’mon! What did Tim tell you?”
My heart beat a full twenty beats, which seemed like forever, before I answered her.
“He said you like to watch,” I blurted out. “He said you wanted us to get together so you could watch us.”
Gina looked back into my eyes, still grinning her enigmatic smile.
“And what? You wanted to know what he said, and I’ve just told you. Then you came back and we went on like nothing was said.”
“And what did you think about it?” She was clearly smirking, now, still so cool, totally in control.
“I haven’t really thought about it. I mean, that sort of thing just isn’t on my menu. Is it true? Is that what you want?”
“Yep. I want to see when it happens. I want to watch. That would turn me on, I think, probably more than anything else I’ve ever done in my life. Is that so wrong?”
I was simply flabbergasted. Here I’d been wanting this woman all to myself for all these years, but what she wanted was to watch me turn into a gay guy or something. A little glimmer of hope was worming its way into my psyche, though, as I thought about it. Could this be something I could really do? And if I did it, would it gain me access into Gina’s body, alone, later on? Perhaps I could negotiate a little 3-way with her and another woman if I did this one time.
“Sam, I can see that you’re considering it. Why don’t you just admit it? It would be so hot!”
I looked to find her actually flushed with excitement. Her nipples were poking out in her t-shirt. Her eyes looked like they were on the verge of tearing up. My eyes were all over her, noticing each and every detail. Suddenly, she appeared vulnerable to me. She’d opened up to me at last, and that meant that there was only one conceivable response, if I were to have her at all.
“What would I have to do?”
She sighed in relief, her hands clasped tight where her legs met. The tension was thick in the air.
“Just do whatever comes naturally. I’ve always wanted to know how a man pleases a man.”
“So, I’d have to be…like…active? You want me to do it with him like I’d do it with you, or something?”
“No. Don’t think about it too much. Just try it out and let it go wherever it goes, Sam.” She looked deep into my eyes again. “I don’t want you to do it if you think you’ll freak out or something, but I always thought of you as, well, as a more open-minded sort of man. I think you’d enjoy it, once you got over yourself and really let go, for once.”
I lit up a cigarette, and noticed my hands were shaking. This was going to be a huge step for me, but one that I knew I would take, for her, if for no other reason. Images were flashing through my mind like a runaway train, now, and my heart was beating so hard it felt like it would pop through my chest.
“And…you’re just going to watch us? You won’t join in?”
“Well, that’s the way it’s always been in my mind. I watch. The two men do whatever they do, and maybe one of them stays, afterward. I don’t think I could join in, the first time it happens. I just want to see it.”
I laughed nervously again.
“Gee, you don’t expect much, do you? Would you do something like this for me, with another woman, the first time we did anything sexually?”
“I have no interest in women, Sam. It just wouldn’t work.”
“But you think I have a thing for men, huh?”
“No. I don’t think you’ve thought about it. My bringing it up has put it right there in the front of your mind, though, and I don’t see you running away. In fact,” she paused, looking down at my pants, “I think it turns you on a bit, doesn’t it?”
I looked down and found myself horrified to see the erection that I hadn’t even acknowledged had grown there. My mind scrambled for something to say, but I was at a loss for words.
Gina simply rose, and strolled to the phone. She dialed, waited, and spoke.
“Tim, could you come back? Sam wants to talk some more, I think.”
I sat there on the couch, red as a beet. I felt completely helpless to change the direction of any part of this conversation, this situation. Gina’s cool, calm, control had returned, and the vulnerability I’d seen in her eyes was gone, now. In its place was pure lust that I’d never seen there before. I knew then that I would do whatever it takes to fill her need.
She got me a beer, and it was gone almost as soon as it hit my hand, so she got me another one. I was sipping it when Tim returned, grinning obscenely as he entered the room.
Gina had moved to a rocking chair. She was sipping a beer as she watched Tim settle in beside me on the couch.
Tim reached into his pocket, and took out a small package. He opened it carefully, and I could see white crystals in a small plastic bag. He poured the entire contents on the glass-topped coffee table, and started the ritualistic chopping of the cocaine. I sat silently as he prepared it into several lines, my eyes going from his handiwork to Gina and back again. Gina’s eyes were glistening as I’d never seen them before, almost like she was in a trance state.
Tim hadn’t spoken a word since his return, he just hummed a little tune as he worked. With a flourish, he pulled a little straw out of his pocket. I noticed it was a fast food straw. He unwrapped it, cut it in two with his little razor blade, and handed me a half.
I glanced at Gina. Her eyes were all over the two of us, and I was beginning to feel more like an object than a person. This was a new feeling for me, and I found myself getting into the role of performer. I took the straw, and snorted two long lines up one nostril rather quickly.
Tim took his straw and repeated my actions, then he wiped his finger on the table top, and ran it over his gums. His finger returned to the little rails of dust. He gathered some up, and put his finger in my mouth. My eyes flashed to Gina, and I sucked on his digit slowly, feeling the drug’s effects rapidly spreading throughout my body even as the stuff numbed my tongue.
He leaned in and kissed me, his tongue forcing its way into my mouth. I could taste the bitter numbing coke on my tongue as his hands began to roam over my chest. He was tweaking my nipples just like I would have done to Gina. Suddenly, I felt very feminine, and very passive. I leaned back, placing my hands on Tim’s shoulders as we continued the kiss. He was squeezing my pecs like they were breasts. My cock was hard as it’s ever been, and it felt uncomfortable, the way it tented up my pants. My feet came off the floor, and my legs rose, trying to get my cock to point in a more comfortable direction. His hands went right to my ass, and I froze up for a second as he gripped me very tightly there. My fingers were digging into his shoulders, but my legs stayed right where they were. It was like my body was offering my ass up to Tim without any approval from me. A low moan escaped me before I could rein it in.
Tim broke our kiss, and my eyes went self-consciously back to see Gina staring at us, her eyes wide, her hands gripping the arms of her chair very hard. Then Tim’s fingers began brushing across my ass, teasing toward my hole through my jeans. He was kissing and sucking at my neck, now, and I was helpless in his grasp, my breath coming in little gasps as he had his way with my fully clothed form.
“Stand up,” he whispered.
“I don’t know if I can,” I breathed shakilly.
He deftly opened my pants and pulled out my throbbing cock.
“Stand up,” he repeated, and this time I complied.
“Take off your shirt,” he ordered, and as soon as I had done it, he had me remove the rest of my clothing.
Tim sat back, and I could almost feel his eyes moving over me. He directed me to turn around by twirling his finger, and as I turned, he ordered me to stop.
I was facing Gina, our eyes locked. Tim pushed on my back, and I found myself bending over for him, still keeping eye contact with Gina. I felt Tim’s hands roaming over my legs, then they ran up the inside, and he cupped my balls. He reached further forward, and grasped my aching member, and pulled it back between my legs. This forced me to bend even lower, and my eyes left Gina’s. I gasped as I felt his tongue, then his lips on my cock. I found myself rocking back and forth like I was getting fucked, as he sucked my cock. My hands went to my knees to steady my position. His mouth left my cock, but he stroked it in his hand while he sucked my left ball into his mouth. I gasped again as I felt his warm breath through his nostrils right on my asshole. I was feeling even more vulnerable with my ball in his mouth, which in turn made me feel even more feminine, for some strange reason. Evidently, femininity equates to vulnerability, in my mind, and as that thought flew through my racing mind, Tim let my ball fall out of his mouth, and he stuck his tongue in my ass.
If he hadn’t had a good grip on my cock, I would have fallen over at this point, but he was actually using my cock to pull my ass into his face. I’d never experienced such a warm pleasurable invasion in my entire life. My hands left my knees, and went to spread my ass cheeks, all without a single volatile thought from me. My legs were shaking.
“Go get on the bed. Wait! Take another line first,” he suggested. his finger swiped up a line, and he pushed it directly into my asshole. Then his tongue returned, and I felt the warm numbing that both the tongue and the drug brought, as I used my straw to snort up another line.
My legs felt like rubber straws as I climbed into the bed in Gina’s room. Tim and Gina soon followed me, Tim holding a towel. He put it on the bedclothes under my knees, and then stood and stripped himself off. Gina sat in an overstuffed chair, spun it around, and continued to watch us, as Tim stepped up to wave his rather large cock in my face.
“Give us a kiss, then,” he purred, as he gripped the back of my head and guided me to suck the thing.
The warmth on my tongue, the velvety smoothness, and the power of the flexing muscle, were the first impressions I got as I sucked my first cock. As my tongue danced on the pulsing rod, I searched for a flavor, but the coke had numbed all taste from my mouth. I was thankful for that, in a way, as he began to pump into my face like he was fucking me. The numbing drug did keep me from gagging, and I found myself actively slurping him as deep as I could into the warmth of my mouth. I kept getting these flashes of femininity in my mind, and I suppose that that’s the only way I could cope with it all, to be “like a girl.” I found my fingers were digging into his asscheeks as I guided him in my mouth.
“Okay, my turn,” Tim gasped, pulling his cock out of my lips.
I lurched forward & gave it one last lick, my eyes meeting Gina’s again as I smiled at her. Her expression was one of deepest concentration, and I felt like my smile was silly, so I looked away as Tim guided me to lie on my back.
He knelt between my thighs, dipped his head down and sucked my entire length into his mouth and throat. No one had ever done that to me before, and my inhalations were more like sobs as my body shuddered in new pleasure. My hands went to his head. His hands went to my nipples. He pinched them roughly, and I grabbed his hands as I thrust my cock to deeper regions in his mouth. He let go of my nipples, and I frantically rubbed the pain out of them as his hands went everywhere at once, it seemed. Then they zeroed in on my ball sack, and then to my asshole. I glanced to Gina with my hands palming my “tits.” Her eyes were on Tim, then they locked onto mine. Her lips curled up into the barest hint of a smile as she ran her hands over her own breasts, echoing my motions. I again felt myself blush, but kept my hands where they were, and watched as her right hand dipped into her sweatpants. Her eyes closed for as moment as I could see her clearly diddling herself, and when they opened again, our gazes remained locked on each other.
Tim’s hands slithered behind my knees, and he was raising my legs up high. I knew what he wanted. I didn’t want that. I couldn’t stop it if I tried. My body began to curl up to give him access wherever he wanted it, and soon his tongue was fucking my hole again. I was breathing like a locomotive, and Gina was obviously enjoying the show as she shuddered in silence, her eyes closing for a split second before returning to the scene before her.
Tim’s finger was penetrating me, and that worming tongue was all around my flexing portal. Suddenly, Gina rose, went to a drawer of her nearby desk, and soon she arrived at the bedside to deliver a jar of lubricant to Tim. Her eyes twinkled at me, and I knew I had to do this for her. She wanted it. Not me. This was for Gina. That’s where my mind was as Tim smoothed that slippery stuff onto and into me. I felt myself relaxing for it, nay, pushing back onto his questing fingers. How many were in me, I wondered. The numbing coke was starting to wear off, and I was trying to count them, to feel how spread open I was, as I continued my stimulation of my own nipples without even recognizing it.
As Tim placed my ankles on his shoulders, and settled in to a good fucking position, my mind started to panic. This wasn’t exactly what I’d had in mind when I’d agreed to all of this. I’d expected to maybe suck his cock, give him a hand job, and get the same in return. I didn’t feel ready for an old-fashioned ass fucking in front of the woman I wanted to bed, yet there I was, displayed for her perusal, open, and, yes, eager for it on some level. That spongy cock-head rubbing around my sphincter felt so warm, so soft, so smooth, so good, I couldn’t seem to help myself. I looked down to see my hands spread open, my fingers splayed wide, as my palms were rubbing in circles over my nipples. Then Tim pressed his cock in, and it popped through my last line of defense before I could even think of resisting. All of his teasing and playing at my ass just seemed to make it perfectly pliable, open for his desire.
There was no pain as it entered. Only a feeling of opening up, of being filled to the fullest, as my hands squeezed into my pecs. My eyes went back to Gina to see her standing by the bed, staring at my invaded ass, as Tim just kept the prod driving into my depths until he bottomed out with a sigh. Once he was fully embedded in me, Gina looked into my eyes. I reached out my hand, and she took it and gave it a squeeze, before placing it on Tim’s shoulder to join my ankle there. I grasped both ankles in my hands and spread myself even wider apart, to feel him enter me as deeply as he could possibly get. The overwhelming physical and emotional sensations of that moment will be forever imprinted on my mind.
I looked Tim in his eye and said, “Fuck me, Tim. Fuck me good!”
He began the old in-out motions, gently at first, but soon was humping into my hungry flesh as hard as he could, at my begging insistance. He let my legs down, and I wrapped them around his waist, my heels kicking his ass to get him to fuck me harder yet, my hands at his shoulders, my eyes locked onto his. I stretched up and kissed him, then. He kept fucking me like this was to be his last act on Earth.
“Let me up! I want it from behind!” I mewled.
Tim laughed when I whined at his withdrawal, and laughed again as I got into position as quickly as I possibly could. I had to have that cock back in my ass, and I’m sure both he and Gina knew it as I begged for its return.
I thrilled to the feel of his sack swinging into mine as he hit home. I was rocking on his long warm thick cock so hard, so fast, that all he needed to do was stand on his knees and let me fuck myself on it. I imagined huge breasts clapping together on my chest as I got so royally fucked. I was back into that feminine frame of mind, it seemed, and loving every second of it. I felt like I could take the entire world up my ass, and it might not be enough. My fingers gripped the sheets in an iron hold as I thrust my ass back again and again. I was tiring myself out, but I couldn’t seem to stop, My breath was coming in ragged sobbing gasps. My toes were curling up into tight little fists on my feet. My legs were pumping my bottom back and forth onto that lovely warm throbbing penetration. My heart was beating at an alarming rate. I was begging him not to stop, and sometimes I was just spouting ecstatic jibberish.
All too soon, I felt him grip my hips tightly, his fingers digging into my skin. He held me still for a moment, and I could feel his thickness swelling inside me. Then he lay down onto my back, reached under me, and gave my cock a few strokes. I felt the hot pulsing splash of his seed burning inside me even as I felt my own spurting out of me. I howled in need, I pumped my juice onto the towel under me. I rocked back on his softening member, still wanting more, more and even more, as he began to shrink inside me.
The words spat out of my mouth before I could stop them, when his cock shrank & began to slip out of my stretched out fuckhole – “no no no NO!” and I fell onto the bed on my stomach.
The two of them laughed softly at my cries, and I blushed as I looked into Gina’s face to see her smile. Then my eyes travelled down to see that she was naked, save for a rather intimidating strapped on dildo jutting out from her loins.
“Looks like you’re hooked, Sam,” she grinned. “Maybe I can help out a bit?”
As Tim slipped off my still-gasping form, my legs spread wider all by themselves, it seemed, and soon I was again filled to the brim, but this time by the woman who I had wanted to fuck just like this for so long. Gina fucked me good and hard that night, and it was days before I felt ready to try anything like that again. Tim was the watcher, this time, though he took his role much farther than Gina had. His hands and lips were all over me, his words of encouragement prodding me along with Gina’s phallus. His presense seemed to give her impetus to fuck me even harder than Tim had. I was a raw worn out rag doll when they finished working me over. Gina and I cuddled while Tim dressed and left us, with her cock still inside of me.
It’s been a couple of months since I lost my “gay-ginity,” as I tend to think of it. These days I find myself dropping in more frequently than ever before. Yeah, I eventually got to fuck her, too, and it was unbelievably great. I can’t get enough of Gina’s warm mouth, her hot pussy, those fantastic tits, or that beautiful ass of hers, but whenever Gina gets in the mood to fuck me, well, I have to say that I have never refused her, and I doubt that I ever will.
Gina said she wants to watch again this weekend. She’s invited Tim and another guy over, and she says she wants to watch them tag-team me all weekend long. Well, of course, I’m going to go for it. Tomorrow’s the big day. I don’t really understand what she gets out of watching me get fucked over and over, but if that’s what she likes, who am I to refuse her? Besides, I find that I really feel totally fulfilled when I have a big cock or one of her strapped on cocks in my ass. I wonder if she’s turned me gay. Nah! I’m too stuck on her to be gay! I really AM looking forward to it all, though, in a very big way.