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First Time with TS

By: hasnoalias



I came into her house, like I have done on many occasions, only this time she was going to fuck my ass. I have known her for over a year, and while we have been friends, we have never fucked or played around. Then one day she sees one of my emails to a TS group that she is also a member of. I was wanting to have my body used by a hot and horny shemale. She responded, saying that she knew someone who would like to help me out. Over the course of the next few weeks she told me that it was her. Like I said I had known her for over a year and the idea of her being a shemale never entered my mind. And now here I was.

She greeted me at the door in a pair of her tight black vinyl pants. She is very hot; she is about 5'8" with long brown hair. She has a very nice body. Great tits and a nice round ass. She is neither skinny nor fat. She has what most people would call a big boned body type. She looks like she lifts weights, but doesn't have muscles that show.

I have been swimming and running since high school. I swam and ran competitively and got a scholarship for swimming in college. I am in my first year of college now, but still look like I shouldn't be old enough to drive. I have a baby face and I have been told a nice bubble butt. My body is toned and slim. I don't have a bit of body hair, but more on why later. So there she is. She takes me into her room, and tells me to get started. "I want to see how good you really are with that mouth of yours. Now get down here."

I get onto my knees and she pulls my head into her crotch. "Lick and suck my cock through my pants, you little cock slut. I know you want it, but you are going to have to earn it." I am very turned on by this crude and dominating talk. I can feel my cock getting rock hard.

I immediately begin lick and sucking her rock hard cock through her pants. I am very turned on by being ordered around, and being told different rude, crude, and humiliating things about me. I really work her good. And I know she's enjoying it.

She finally tells me to take out her cock, "Okay you cock bitch, come and get this thing."

I unzip her pants and out pops her hard cock, right into my face. I immediately go to town on it. I suck it all the way down, I suck just the head while I lick the pee slit with my tongue. I really give the cock head a good sucking. I imagine I am trying to suck her skull out of her hard cock. I lick and suck her balls. I do everything I can think of to get her really riled up. I try a trick I have learned where I take her cock all the way to my throat and begin to swallow. This gives her the amazing feeling of having my throat muscles stimulate her cock head. She apparently loves all of this attention. 

She starts really working up a nice rhythm fucking my face. And I can see she is enjoying herself. And she keeps telling me what a good cocksucker I am, and how she knows how much I love to suck her cock. This talk just makes me go harder. I look up into her eyes and smile around her cock. I keep eye contact as I am working her hard cock in my mouth. She is in heaven and she is calling me all sorts of names and saying what she will do to me. I even massage her asshole with a finger, but I don't press into her, without her permission. 

She is breathing hard and I can feel her asshole tighten from time to time. She then pulls my mouth off her cock with a pop. She then turns around and bends over slightly. I see that the zipper for her pants goes all the way to the back. She tells me to unzip her. I unzip her pants fully. Her pants are now in two pieces and her gorgeous ass cheeks are exposed and in my face. She says, "Since you seem to want to give my asshole more attention, I want t you to lick it. Lick my ass you little bitch." She then pulls my face into her asshole. My café in now between her ass cheeks and my tongue is teasing her hole. I can hear her breathing loud and moaning. "Tongue fuck me you slut. I want to feel your tongue up my asshole now bitch," she orders. I stick my tongue all the way into her puckered asshole. She is very clean and tastes great. I feel her ass muscles tighten around my tongue as I work in and out. I force my tongue in as far as I can. I work my tongue up and down and from side to side. 

She is loving this too. She keeps saying that she intends to keep me, and that she should have known I was a slut from the first time she saw me. She tells me to stroke her cock while I lick her ass. I reach between her legs and stroke her hard cock. I keep up a good steady pace on her cock, because I don't want her to waist a load of her cum on a handjob. She starts pushing her ass back into my tongue and grinding into my face. She shakes her ass cheeks, moving me with her. 

Then she turns around and forces my mouth, once again onto her hard cock. She doesn't go slow or easy. She pounds her cock into my throat. I have no gag reflex, so this is not a problem for me. She looks down at me and says, "Finger my asshole while you suck my cock. I want your finger in my ass as I fuck your face." I do as ordered and stick a finger in her asshole. I get a good rhythm going there I push my finger in as my mouth is all the way on her cock. Then I pull my finger out as my mouth comes to her cock head. Apparently this pushes her over the edge, because she suddenly screams and rams her cock all the way into my throat. She begins to cum down my throat. I can feel her cock twitch with every spurt of her hot cum. I can feel her cum as it hits my throat. I swallow every drop. I then work her cock in my mouth and suck all of her juices out. I then suck her cock head again. 

She never goes limp. I wonder briefly if she took a Viagra or something to keep her hard. Finally she pulls me off her cock and crawls up onto the bed, on her back. She places a condom on her cock, and adds some lube. She then looks at me and says, "Climb aboard; this is what you have been wanting."

I do as I am told. I mount her thick cock and ease my ass down onto the slippery shaft. I love the feeling of the cock head popping past my ass muscles. That first gasp gets me every time. I lower myself all the way down. I feel her hard cock as it goes all the way into my ass, until I am sitting on her lap. I then start to work up and down her lap all the way from just the tip of her cock in my ass to all the way back down. I start to build up speed, and so does she. She starts to lift her crotch to meet my ass as I am coming down on it. She has hold of my ass cheeks and is controlling my every movement. She is really enjoying me riding her cock.

I am alternate between going up and down. Then I go all the way down and rock my hips back and forth. Her cock is buried deep inside me. She keeps slamming her pelvis into me, plunging her rock hard cock deeper and harder. Her eyes are half shut.

She then pushes me off of her, and places me on my hands and knees. She teases her cock head against my asshole. She makes me beg for her to fuck me. I beg and plead, "Please fuck me ma'am. I need your cock in my ass. Please fuck me." She laughs and asks, "What are you?" I answer, "I'm your cock slut, ma'am." She says, "Damn right you are."

She then grabs my hips and plunges her cock into my ass all the way to the balls. She is now riding my ass doggie style and she is going to town. She slaps my ass from time to time and makes me tell her how much I enjoy her fucking my ass and how much I like a cock inside my ass. I keep pushing back to meet her thrusts. We are both going really strong now and she is really plunging it hard and deep. So hard that I am fighting to stay up on my hands. She enjoys pulling her hard cock out of my asshole and then plunging back in all the way to her balls. Every time she does this we both moan.

She pulls out and with a quick roll, I am on my back with my legs on her shoulders and she is back inside me. She is fucking me so hard that my hard cock keeps smacking my in the stomach. I reach down to work my cock. She grabs my hands and tells me not to touch my cock. She guides my hands to her tits. Then she starts to stroke my cock. She tells me she is going to make me cum so she can feel my ass tense and tighten when the orgasm hits me. That way it will really milk her cock when she cums.

I do as she orders, and begin knead her breasts. I pinch her nipples. She loves this. I hear her begin to moan loudly. She strokes my cock even faster. I won't last long. She keeps fucking me senseless. I can feel my asshole begin to tighten. I thrust my hips making my asshole smack into her crotch and my cock jerk in her hand. I tense up as the orgasm begins to come over me, and with a thrust of my hips, I cum in jets all over my chest and even my face. She groans so hard, and thrust in all the way she can and I can actually feel the cum fill the condom. She looks down at my cum-covered body, and asks, "Is that the way you like to get fucked, you bitch?"

I say between breaths, "Yes!"

She says, "Good because I have someone who wants to join us next time!"

First Time with Two



Studying late in the library was never a good idea. I groaned, cracking my neck in pain. God, hours of macromolecular atoms was not my idea of a good Friday night. I was gonna be celebrating my 20th birthday soon after all. What a lonely life. Needing the fresh air, I walked home and it was already pretty late by then. 

I decided on a shortcut that I heard about from my friend since I just wanted to get back to my room as soon as possible. The air was cold and my surroundings blanketed with an eerie silence. I gulped and walked faster, hearing the chirps of crickets and the hoots of owls in the forest.

The shortcut led me through a dark forest with one paved road. There was only one way in and one way out. When I saw the flicker of lights up ahead, I was thankful. At least I wasn't alone. Little did I know I would come to regret thinking in such a way.

I drew closer to the truck and this frantic man came up to me. "Oh, miss, miss! Can you help me?"

Blinking several times, I managed a curt nod. He was balding and had a slight beer belly but his arms looked toned even though they were hairy. He had slight stubble but it made him look more rugged rather than hobo-like. 

I saw the logo on the van was for a pet shop. "This dog went jumpy in there so I kind of panicked. I thought that we could use a woman's touch in order to calm it down." He gestured to the truck.

"We?"

"My friend and I. He's still inside the truck now."

"Oh. But I don't hear anything."

"That dog is resting between fits. I'm just scared that something's wrong with it. And you seem very knowledgeable, ma'am." He flattered me with a pleading look.

I sighed. What's another few minutes? The inside of the truck was dark when he helped me up into the back. But once there was light that lit up the back, I realized that the place was empty. "Wait, what—"

"Listen up, you little slut, you better do as we say or we'll make you regret it." The man earlier sneered. I realized he had dark messy hair beneath his cap. On the other hand, his companion had red hair and a beard. He was skinny and tall, a complete contrast.

I reared back, "But you said—"

"That was a fucking lie. Now shut the fuck up and get on the floor." He smirked, glancing down at the carpeted floor.

"Hell no," I spat out. "I don't listen to the likes of you."

"Oh, we've got a feisty one. Even better." Skinny grinned maliciously and approached me. 

I yelped and backed myself up until I was cornered. He grasped my arm roughly and threw me onto the ground, quickly pinning me down. He grabbed the collars of my blouse before tearing it open, popping all the buttons off. I cried out as the other man yanked down my skirt. 

"Look at that," Beer Belly licked his lips while his eyes glittered with lust, looking down at my red thong. I blushed furiously. I had worn that in a hurry this morning without thinking. Now, I regret that. "So sexy." He traced the line down my slit, making me shudder. I struggled in Skinny's grip but I could feel my pussy dampening.

"Are you wet for me, whore?" With a flick of his wrist, the brunette tore my thong apart. His stare heated my core and my heartbeat rose with every second that passed. He pushed a finger in without a warning and I shrieked. I tried kicking around my legs but then he pressed them down, making sure I couldn't move an inch as he shoved his finger in and out of my pussy. 

I shook my head, crying out for help. But it was a futile effort when the skinny one covered my mouth while he tried to unbutton his pants.

"Your cunt is dripping wet, honey. You like this, don't you? You like me finger-fucking you don't you?" He sneered, pushing another finger in and continuously pumping in and out of me. I could hear the smack of his fist against my pussy and also the wetness that reduced the intrusion of his fingers. I couldn't believe it! I was actually wet for this!

When I looked up, Skinny had already had his cock out. It was long and lean, it wasn't that thick. Before I knew it, he pried my lips open with his cock and thrusted it in. He groaned in pleasure, "That's right, bitch. Suck my cock. You like it, right? You little cock sucker. I'm going to cum in your mouth and you're going to swallow every last drop of my hot cum." I gagged as he fucked my mouth over and over. I tasted the salty pre-cum from his cock.

With the pleasure building up in my pussy, I was so turned on with sucking his cock. It wasn't too thick which made it easier and I loved the taste of his salty cum on my tongue. I grabbed his cock in my hand and stroked it up and down while my tongue swirled around the purplish head. When I pulled back, I noticed the pre-cum oozing from the top of his dick and I quickly lapped it up. God, he tasted so good.

The guy playing with my pussy had released his cock. His cock again was a contrast against his friend's. It was shorter but so much thicker. He jerked off in his hand first, stroking his cock, making it bigger and longer. Then when he looked extremely hard, he quickly pushed it inside of me. I cried out at the suddenness of it but relished in the feeling of being filled completely. He roughly thrusted into me over and over and the pain slowly turned into pure, raw passion. 

"Fuck yeah," he smacked my ass while still fucking my pussy. "You like my fat cock inside you, bitch! I know you do you little slut! You're a cock-sucker too huh?" He chuckled darkly as my pussy tightened around his thick cock.

"Hey, Barry, wait for me." Skinny yelled out and swiftly pulled his cock out of my mouth. My mouth felt dry as I panted for him. I missed the feel of his cock inside my mouth. What the fuck? 

Barry flipped us over so that I was riding him. He shook off his shirt and I ran my hands all over his body, the curl of hair on his stomach and I pushed his cock deeper inside of me, whimpering when I felt it touch my womb.

Skinny propelled me forward, so that my breasts were crushed against Barry's chest. He groaned and palmed my tits. He grabbed them and pushed them together, rubbing them to each other. "Fuck, you've got really great tits. So fucking perfect," He ripped off my bra, tossing it aside, and licked one of my hard nipples. I arched my back, pushing my breasts to his face. He eagerly took one pert bud into his mouth while his hand grabbed the other, pinching my nipples, sending delicious jolts of pain through me.

I almost jumped off Barry's cock when I felt a finger probing into my anus. "Hey, don't! I've never—"

"Oh, baby, you've never been fucked here?" Skinny poked it again and I pressed closer to the man beneath me. He touched the area where Barry's cock met my pussy, taking my juices and coating his finger with it. 

It became his lube as he pushed a finger inside my asshole. I winced, "Don't please."

"Shut up, bitch. You don't have a say in this. You're just our whore right now. All you have to do is readily take my cock inside of you and I will cum inside your ass and you'll enjoy every bit of my hot mess inside you." He devilishly smirked again then spat into his hand, stroking his cock. He yanked me off of Barry and instantly thrust his cock inside of me as I knelt on the ground.

I screamed in both the pain from his intrusion and also the pleasure of having his long cock probing into my depths. Barry on the other hand shoved his fat cock into my mouth, stretching my lips. He grabbed my head and thrust into my mouth over and over. "Yeah, bitch. Take that cock. You know you like my fat cock in your mouth. I'm gonna cum so hard, baby. That's right, take it!" His thrusts increased and I took hold of his cock, stroking it from base to tip while sucking on the cum he had so far. 

Then Skinny shoved me off him. I stumbled forward, meeting the floor. "Now that I'm lubed with your cum juice, I'll fuck that tight ass of yours while Barry takes your tight little pink pussy. And you'll enjoy every second of it."

I hadn't even said anything when Barry positioned me on top of him again. He shoved his thick cock back inside my pussy and began thrusting from underneath me. While I was moaning in pleasure from Barry's fucking, Skinny forced me to lean forward and then I felt the sharp pain pierce through me as he had forcefully pushed his cock inside of my asshole. I screamed in the agony of it. God, it was so painful but the feel of both cocks moving inside me at the same time, the way the two rubbed against each other with me as the barrier was absolutely fantastic. I moaned and moaned as the two men grunted and smacked my ass over and over. Skinny kept spanking my ass as he grabbed my tits, squeezing them hard. The burn on my ass felt delicious against the pain of the two cocks inside of me. Meanwhile, Barry just enjoyed the view while reveling in the feel of his cock inside of me.

My pleasure continued to build up and I felt my body tense all over. My asshole and pussy both squeezed the two cocks tightly and I heard their grunts of approval and I knew they were close as well. My heartbeat kept increasing as the tension did too. Then it happened.

Earth-shattering orgasm.

"Fuck," my pussy pulsed with my release, drenching Barry's cock with my cum. Both my holes milked the two hot cocks dry as they filled me with their salty cum. I slumped on top of the man beneath me as he jerked his release. 

When it was over, I was exhausted but beyond satisfied.

"So, how did you like that?" Barry smirked knowingly, buttoning up his shirt.

"So. Fucking. Good." I groaned out.

"We'll take you home, sweetheart. As payback for your pussy and that tight asshole." Skinny smiled, a bit more warmly this time. "If you need to do this again, remember to just call Sal's Pet Store."



First Time with Viagra



I decided to take the purple pill to experiment and see what effect it would have on me. I am not an ED focused person, my equipment has always worked very well when called on and has served me faithfully for some 50 years. I get stimulated quite often and the combination of sex with my partner and masturbation shows no sign of inadequacy, at least in my experience. If I were to rate my performance with a partner I would have to say, I am always "up" for the experience and my penis is eager to accomplish said task. That said, I have thought that my performance might be a bit rushed (like I need to cum or I won't be offered the chance if I wait). After the climax (volume of ejaculate is a bit reduced lately, I suspect because of age and frequent ejaculations (about a once a day average)) I fairly quickly shrink and return to a relaxed, non-aroused state. I have been with a partner for several years and I think our sex has resulted in me treating myself to a climax and she enjoying the company, sometimes leading to an exciting time for her – mostly by her own hand, but always with me cuming in fairly short order. Pre-mature ejaculation? I don't really think so since I am always enjoying the warmth of her vagina and she whispers in my ear "go ahead" and then WAM, I cum. 

As a side note, I have had sex with a different partner several times and that experience was always quite different. We, the other partner and I, would enjoy the pre-sex talk and touch, and then she would mount me while I was on my back and she would writhe in several climaxes while I was "up" and penetrating her. She seemed to really be enjoying the erotic/sexual/sensual experience and while she was experience her ecstasy, I was accommodating her quite nicely. After several orgasms' she would then let me know it was time for me to take over and would roll over on her back and I would then make love to her in the classic missionary position (where did they come up with that name anyway?) and within a short while I would climax. The point of this, other than to bring back some nice memories, is that with her I would quite nicely accommodate my lover and hold off cuming until it seemed like a good time to let er rip!

Anyway, I come back to the topic with "why would I want to take Viagra?". I found myself with several hours (actually days) by myself and I always enjoy having a sexual experience within the confines of my home and my marriage commitments. Being alone is a stimulating event for me in that it affords me an opportunity to be quite sexual all the time and experience the pleasure of sexual tension and release, repeated as often as desired. So here I was with time on my hands, alone, and thought: why not, lets see what happens with Viagra, what is all the fuss about? (as an aside, I never ordered the Viagra, it came free and a sampler with an online order of some meds) I was experimenting. What did I expect? Well, I had heard/read the warnings about ....if your erection lasts longer than 4 hours seek medical assistance... that didn't sound so bad – being erect for a while,,,, however the real desire is to be sexually charged and then have the pleasure of release, and then maybe again, and, then ...you get the idea. I didn't really believe that Viagra would give me wild multiple-organism experiences, but would rather allow me to stay hard and that seemed erotic in and of itself. The eroticism then I believed would lead to more pleasure seeking and experiencing. Anyway, it was something to try and the thought was also that if it was a good experience, possibly I would try it with my partner and maybe, post climax, be able to pleasure her in a continued way...

OK I popped the pill at about 6:45am and set off to do other things. They say that it takes about 30 min. before the effect sets in. In about 30 minutes I started to feel flushed in my face. I felt a bit more jittery I started to get into the effect – warmth, and my heart starting to pump a bit harder. I didn't have an immediate erection but I could tell that I was relaxed and could get erect quite easily. (reminder, getting a hard on was never an issue). About 45 minutes in I was on my laptop and found myself reading some stimulating information about masturbation. I had a cup of tea and continued to read. I noticed that I was getting hard. I also noticed the pre-sex jitters coming form being excited. Also I noticed that my nose got stuffed up and that seemed to go with the feeling of being flushed. At one point I had to pee and when I took my penis out of my pants it was semi-erect (about 60%) and I had a good sized drop of pre-cum on the tip. I urinated and stuffed it all back in my pants, now mostly erect and returned to my Laptop. At another point I touched my face and massaged it and realized that I was really enjoying the sensations and the more I touched my face and neck the more stimulated I became and this went on for about 30 sec. I was breathing hard and I was quite sexually stimulated, and yes my cock was pushing to get out. I returned my attention to my Yahoo group exploration and came across a Hypnosis group that seemed to be oriented tword S&M. While that was not my intent I did come across good deep hypnotic generating audio file.

I made myself comfortable and for the next 20 min or so was led into a deep hypnotic state with no particular suggestions other than to be able to go deeper the next time. I did notice that I had gone soft (lost the hard-on) I guess that comes from being really relaxed. I then got up went to the bathroom and took off my clothes and proceeded to take some pictures of my really erect cock (it got that way quickly) – it stands out 90 degrees when I stand up and it was really hard. I then gave myself and enema (I enjoy anal play) and while in the shower masturbated – it was all quite exciting and I had quite an orgasmic rush. After I came I took a long hot shower and got out still a bit hard. I think my hard on lasted another 20 minutes and I returned to my laptop and entertained myself for a while. I did get up again in about an hour and in a semi-flaccid state and went to the bathroom, applied some lube and masturbated. I came in about 2 minutes and It was a good orgasm while I wasn't really hyper, I felt hard but not erotic, the stimulation felt good and I kept that in my mind and I eventually climaxed. 

I noticed the clock at about 4+ hours in and I was back to my old self with no flushed feelings and no real left overs that I was aware of. I did remember having a bit of a metallic taste in my mouth near the beginning of the experience. Also as mentioned at one time while I had a quickening heart beat and high sexual excitement, I also experienced a sense of calming and slowness. I walked slower and more deliberate – not sure what that was about other than just focusing on the experience more fully – concentrating on the feelings I was having – possibly the same effect that I was having when I was touching/feeling my face and kinda grooved on that... more intense sensations?

All in all a good experience with no lasting after effects.... Will defiantly try again.