I didn't want to do this. I knew that if I told Kendra about Tina after we did this, it was going to appear as if I was a total asshole who had taken advantage of her. Having anal sex with her for the first time only made the entire spectacle look even more unsavory. Besides, if there was anything that I had learned about sexual relations from Tina, it was that men and women can only be mutually respectful partners if they are completely honest with each other about their sexuality and all it encompasses. If this had happened a week ago, I would have had no moral qualms about it, but knowing what I now knew made me think that this was dishonest.
On the other hand, either I was going to disappoint and anger her now, or I was going to do it later. In some ridiculous stab at rationalization, I reasoned that at that very moment I was naked as a jaybird and sporting a throbbing erection, and I assumed that that wouldn't be the case in the morning. Better to anger a woman when your cock is concealed and at ease, I falsely reasoned, than to do so when your prick is conspicuous and excited!
I didn't say anything, but I made it clear that I was acquiescing. We retreated to Kendra's bedroom, where I spied a bottle of lube and a hand towel on the nightstand. Then regrettably, I resumed my usual role as the primary instigator in this sexual relationship. I began peeling her little, black dress off her.
Kendra wasn't kidding when she said she was prepared for me. What I found underneath her dress got me even more excited. She was wearing some kind of black, harness bra and matching G-string. The front of the bra reasonably concealed her tits, while the front of the G-string barely covered her thick, dark, trimmed bush. But the back of each was a different story – they essentially consisted of nothing more than a series of strings that wove their way around her slender back and shapely derriere.
I unbuttoned three buttons that held her dress tightly against her cleavage, and then I eased that little, black number down her bosom, waist, and hips until it fell harmlessly to the floor, and she was able to step out of it. I left her heels on. I pulled her tits out of the cups of her bra, but left it on. It just looked sexier that way.
Then, Kendra crawled onto her huge bed on all fours, tantalizing me with her tight backside, like a trainer dangling a carrot before a horse. I followed her onto the bed, and grabbed her butt cheeks with both of my hands, and began caressing her taut skin. Then, I leaned forward to pay homage to her ass.
I only had to spread her cheeks apart and move one string aside to reveal her virgin hole to my lustful eyes. Then, I went down on her tight, little starfish and began alternately licking her voraciously and gently fingering the slick, quivering tissue of her hole. "Oh my god, that feels good!" she cooed. I was leaving behind abundant amounts of saliva as I tongued her. It would soon serve as additional lubrication once Kendra was ready.
Then, while I continued to tongue her asshole, I pulled the front of her G-string aside so that I could enter her pussy with my fingers. Kendra was soon breathing deeply, moving her hips against my urgent probing, and softly mewling her approval.
I bent down further and moved my face to Kendra's now leaking pussy and began to run my tongue up and down her lips. I withdrew my fingers from inside her and used them to spread her lips wide open, so that I could run the flat of my tongue all the way from her clit hood to her asshole. I could feel her arousal running down the length of her vulva until her small, but dense patch of dark brown pubic hair was saturated with her juices.
I wanted to make Kendra cum before we embarked on something she'd never tried before. In my experiences, not every woman enjoys anal sex. It seems as if they either love it or hate it. If Kendra didn't like it, I at least wanted her to have enjoyed what came before. I figured that meant making her cum by eating her pussy. So I placed my left hand on her tight ass, with my palm facing down, and I reached my thumb to her gushing sex. Then, I began sawing it back and forth inside her, unleashing another round of erotic groans and an additional flood of arousal.
"Oooooooohhhhhhhh! Oh my god, that feels so good, baby! Keep fingering me!"
And then I went for her clit. While I continued to finger her wet pussy with my thumb, I wrapped my mouth around Kendra's pink pearl, sucking it deeply into my mouth, where I could flick just the tip of my tongue back and forth across it, darting here and there, making direct contact and then backing off, pleasing and then teasing. Then, I altered the motion, moving up and down, and then changed things up again, swirling around it and over it with my tongue.
"Oh, lick my clit, Evan! Oh fuck! Oh fuck! You're gonna make me cum all over your face! I'm really close, Evan! Make my fucking pussy cum; make it cum!"
So, I stopped teasing, and began urgently sucking her clit into and out of my mouth while I continued relentlessly tonguing it, until I could feel the spasms starting to build deep inside her. Finally, she screamed her release, "Fuuuuuuuuuuuuuuuucccccccccccccccckkkkkkkkkkkkkkkk!"
I could feel her pussy convulsing around my thumb, and then I felt a rush of warm fluids bathe my face. Kendra's knees were quaking under her, and then I saw her upper body slump forward and she fell onto her tits on the mattress. Her orgasm lasted a long time, and throughout she was breathing really quickly and whimpering softly.
And now I was really excited myself, and I wanted to be inside her. It was going to take me awhile to prepare her ass for my cock, and I figured I might as well enjoy her pussy in the meantime. Before I did, I reached for the lube and hand towel on the night stand, and dropped it onto to the bed where I could reach it when I needed it. Then, she got back up onto her hands and knees, and I peeled Kendra's G-string off her. I was rock hard, so now I just withdrew my thumb and replaced it with the head of my cock. Then, I thrust into her pussy in one long, slow stroke.
"Oh my god! You're so big! Jesus Christ, you're gonna make me cum again!"
Then, I started moving in and out of Kendra's frothy sex. I grasped her hips with both of my hands and began building a steady rhythm. She was looking back at me now, and her face was painted with the most erotic expression – her stunning blue eyes spoke to the pleasure she was deriving from every thrust, and her mouth formed an "O" that appeared poised to elicit sensuous words, but instead produced only a string of feral sounds whose cadence matched the rhythm of my thrusting, "ugh... ah... oh... ugh... ah... ohmagod... ugh... ah... oh... ohmagod... ugh... ugh... ugh..."
Then, I picked up the bottle of lube with one hand, while I continued to hold Kendra by the hips with the other, and I squeezed a big dollop of lube into her tight little hole that seemed to be egging me on, urging me forward, and then, just as I had done earlier, I put my free hand on her slender ass, and with my thumb now slick with lubrication, I used it to enter her virgin backdoor. As I pushed gently, I felt her sphincter muscle give way, and my thumb slid in all the way to the knuckle.
She responded with an elongated and vulgar groan, "Aaaaaaaaaaaggggggggggghhhhhhhhhhh!" Then, I began moving my thumb back and forth, beginning my protracted preparations to enter Kendra's virgin ass with my manhood. What I hadn't appreciated was that she was already really close to reaching another climax, and with my vigorous thrusting and the additional sensation that my thumb was producing, she was right on the edge.
So I was unaware of the effect that my next move would have. I withdrew my thumb and, after squeezing another stream of lube into her slick hole, I repositioned my hand so that my index and middle fingers could enter her simultaneously. They initially met the same resistance as my thumb, but then I slowly slid my joints past her slick opening and soon my knuckles too were snuggly gripped by her tight hole.
As then, Kendra commenced another extended round of shuddering. Her asshole was amazingly sensitive, and I could feel her convulsing around my two digits. She let out another erotic moan, "I'm cumming! Oh fuck, I'm cumming again! I'm cumming again! Aaaggghhh! Aaaggghhh! Aaaggghhh! Aaaggghhh! Aaaggghhh!" The tremors shook her slender frame, as I continued to saw my fingers in and out her tightness and my cock deeply into and out of her creamy pussy, withdrawing all but my engorged helmet on every stroke. Kendra rode both throughout another long, drawn-out orgasm.
I was happy that I had made her cum so easily, but I now realized that Kendra was about to become one of those women who fall in love with anal intercourse. I hadn't even entered her yet, but I knew that she was destined to become a devotee. Under the circumstances, that wasn't a good thing.
Then, I added more lube to her ass, before introducing a third finger to her now gaping orifice, and I continued to stroke in and out of both of her holes. "Oh my god! I didn't think it would feel this good! Jesus Christ! Oh baby! I want your cock! I'm ready for it!"
So, I withdrew my throbbing meat stick from her pussy, and doused it in lube. Then, I pulled my fingers out of her tight ass and replaced them with just the head of my prick. When my bulbous knob pushed past Kendra's sphincter, she turned and stared back at me with a look of disbelief. "Holy shit! You've never been this big before! Oh my god! I don't know if I can take all of it!"
I looked down, and I think Kendra might have been right. I don't remember being as engorged as I was at that very moment. "I'll go really slowly, baby! But you tell me if it hurts at all, even just a little bit, and I'll stop!"
"I don't want you to stop! It doesn't hurt, but it's so big! I think I can... I think I can take more of it! I want the whole thing!"
"Okay, baby, but you need to start touching yourself while I push my way into you! Rub your clit, baby! Don't stop rubbing it! I've got a long way to go!"
So, she began massaging her clit with two fingers. And pretty soon, through that thin membrane that separated her two erogenous zones from each other, I could feel her fingers thrusting in and out of her pussy. She was alternating between rubbing her pink button for thirty seconds or so, and then fucking her seething hole with her middle and ring fingers for another minute. All the while, she never stopped moaning.
I started to gain a half an inch here and another quarter inch there, and after 10 minutes or so, I had half of my cock in her backdoor. She was breathing really deeply now, and every time I pushed a little deeper, she held her breath momentarily, before emitting a long, low growl. Now, I was poised to enter her with the thickest part of my shaft.
I looked down and saw that I had all but about an inch of my manhood inside her, and I wanted to try to fully impale her on my erection. "Okay, baby! Are you ready for the last part of me?"
"Oh my god! How much more of it is there? I can't believe how much you're filling me up! But it still feels really good, and I want you to start fucking me with it! It's a completely different kind of feeling, but I know you're gonna make cum once you start thrusting! Just go slowly once you start moving, please?"
"I will. I promise." So, I started to push the last few centimeters into her slick anus, and as I did, I squeezed some more lube onto the base of my cock. When I was finally in to my root, I told Kendra. "That's it baby! You took it all! Are you okay? Do you want me to start moving?"
"Jesus fucking Christ, Evan! You're huge!" She took a deep breath. "Oh my god! Okay, you can start fucking me now! Just go really slowly." She went back to rubbing her clit with two fingers, wrapping her middle and ring fingers on either side of her clit hood and sawing her them back and forth around that long, slender jacket as she massaged herself.
I started to withdraw, but I only pulled out an inch or so before I moved back in again. "Oh my god, that feels good! Holy shit! You're gonna make me cum again! Keep moving, baby! Fuck my ass! Fuck my ass with your massive tool!"
So I slowly began to increase my pace and the length of my strokes, and in 10 more minutes I was penetrating her with at least half of my throbbing cock. And once I did, Kendra was soon lost a different world. She was grinding her fingers over her sensitive pearl and then plunging them back into her sex, while long, guttural sounds emanated from deep inside her, "Ugh!... ugh!... ugh!... ugh!... uugghh!... uugghh!... uugghh!... uugghh!... uuuggghhh!... uuuggghhh!... uuuggghhh!... uuuggghhh!...uuuugggghhhh!... uuuugggghhhh!... uuuugggghhhh!... uuuugggghhhh!... uuuuuggggghhhhh!... uuuuuggggghhhhh!... uuuuuggggghhhhh!... uuuuuggggghhhhh!"
Then, she slumped forward so that her ass was sticking up in the air, while her upper body fell forward onto the bed again, and her face was turned toward me, but there was no comprehension evident in it. Kendra didn't know where she was or what was happening to her. Instead, all she could do was feel, feel me thrusting fully into her, and then the quaking began anew, and she was cumming again, her whole body was cumming now, "Uuuuggggghhhhh!... uuuuuggggghhhhh!... uuuuuggggghhhhh!... uuuuuggggghhhhh!... uuuuuggggghhhhh!... uuuuuggggghhhhh!... uuuuuggggghhhhh!... uuuuuggggghhhhh!"
I could feel her asshole convulsing around my thickness, and, at the same time, I could feel that she had thrust all of her fingers inside her pussy as it too trembled around her invading digits. But, in fact, it wasn't just her erogenous zones that were orgasming; every muscle in her body was twitching and jerking involuntarily, and feeling Kendra's own climax washing through her, put me over the top.
I could feel the electricity arising from my balls, and soon the surge moved through my dick, and I began my own involuntary movements. Grabbing Kendra tightly around her hips, I was thrusting now as hard as I could into her ass, and while I did, I announced my orgasm, "Oh baby, I'm cumming in your ass! I'm cumming in your ass! Jesus Christ, I'm cumming hard!"
And then I felt my thick ejaculate washing through her tight channel, bathing my throbbing member with even more lubricant. I must have deposited at least 10 powerful ropes deep into Kendra's anus, and it was only gravity that kept my seed inside her. Had her ass not been suspended as if in midair, I know my cum would have started to drip out of her.
My orgasm lasted a long time. Every time I thought I was done twitching, I slid back in an inch or so and felt another contraction of my cockhead. Finally, after two or three minutes, I pulled my oversensitive member out of Kendra.
She didn't move. All I could hear was her deep breathing, the dim sound of her heart beating out of her chest, and a soft, but continuous whimpering emanating from somewhere deep inside her. I was afraid that I'd hurt her, and the longer she lay there like that with her eyes closed, her head twisted around as if to look behind her, and her ass propped precariously atop her shaky legs, the more convinced I was that I had gone too far.
I collapsed onto the bed, and pulled Kendra's ass down until she was lying next to me so that I was spooning with her. And then, sure enough, as soon as I did that, I could see my spunk oozing out of her gaping hole. She still didn't open her eyes, and now I was really worried. "Kendra! Kendra! Are you okay? Did I hurt you?" I wrapped my arms around her in a nurturing embrace.
She still didn't answer. I propped myself up on my elbows and tried to turn her face toward me, caressing it gently with my hand. She continued to lie there that way for at least 10 or 15 minutes. I could see that she was breathing and her heart was beating fast, but other than that, she didn't appear to be responsive. I kept gently stroking her pretty face. Finally, she opened her eyes, and then ever so slowly a grateful smile began to wash across it as her recognition of me registered in her intellect.
"You've come back! Are you sure you're okay, Kendra? You had me worried, baby!"
"Oh, I'm better than okay! I probably won't be able to walk tomorrow, but right now, I don't think it's possible to feel more completely sated. Thank you, baby! I really needed that! I think you've ruined me for normal sex now, but my god, that felt so unbelievably good!" Then, she added rhetorically, "Can we do it again soon?"
She kissed me really passionately, and now I was worried again. That night had made tomorrow that much more difficult, and besides my conversation with Kendra, I had somewhere else I needed to be in the morning. We fell asleep spooned together like that and slept right through the night.
I awoke first in the morning. I got out of bed, took a quick shower, got dressed, and made coffee for both of us. Then, I started to review my talking points for the impending disaster that I was about to unleash. Again, this ultimately proved to be a big waste of time. I wound up improvising anyway.
An hour after I got up, Kendra tentatively stumbled out of bed, visibly walking gingerly as she approached the small dining area where I sat brooding over a cup of strong coffee. "You're an old hat at this anal sex business, right? Which comes first the next morning, Evan, a couple of Ibuprofen or a cup of coffee?"
"Neither. They both come at the same time," I said, pouring her a cup of joe, and handing her a pair of pills that I'd already pulled from her medicine cabinet for her. I knew she'd be sore. She threw back the pills with a long swig of coffee and then looked me in the eyes warmly.
"You know, as sore as I am this morning, I wouldn't have regretted last night even if I couldn't walk at all today! That was really something, baby!" She said smiling. A knot was growing in my stomach, and it was only going to get more unpleasant.
"Kendra, I really need to tell you something, and, unlike you, I do have regrets, real regrets that I didn't tell you this last night."
"What's wrong, baby? Are you trying to tell me that you don't want to move in with me?"
"That's only a tiny part of it, Kendra." She got a really disappointed look on her face. "I've never told you about what happened the summer after I graduated from high school. It was a kind of painful experience, so I wasn't disposed to talking about it at all. I've never told anyone about this – no one, not my best friends, or even my family."
I took a big sip of coffee, and I looked deeply into Kendra's blue eyes. Even with sleep still in them, they were stunningly beautiful. "I met a woman that summer at the lab that I worked at. We started dating, and I really, really liked her, Kendra. She was just an incredible person, and though I didn't even really know it as it was happening, I was falling in love with her."
The pain in Kendra's face was palpable, and now I wished that I had had the courage to say all of these things last night. I was reminded of that day in Tina's apartment six years ago when I hid in the bathroom when Justin nearly broke down Tina's door. I was lamenting that cowardly streak that I knew was an unforgiveable aspect of my makeup.
"Anyway, to make a long story short, that woman just disappeared one day that summer, never called me, never wrote me, and I never heard from her again, until the day before yesterday. She wrote me a long letter that explained why she had left, and I don't want to go into all of that, Kendra, especially to you, but she had really, really good reasons for doing all of the things that she did. She didn't really have any choice. The bottom line is that she feels the same way about me that I feel about her, even now six years later, and this week she's coming back here to Minnesota to see me."
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