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Introduction:

Is the end in sight or will Lily be subjected to Bob’s ineptitude again? Would Lily lose the virginity of her last hole?
As Olivia and I parted ways, I figured I would slip back to my hotel and sleep in. It was Saturday morning and I figured my opportunity to finish my mission wouldn’t come until the partiers were out later that evening. Being close to closing time for the bars, there would likely be many people in the lobby so I could avoid being noticed by Bob if he was working. I had both jars that Olivia gave me, having adequately proven their effectiveness and while I didn’t relish the thought of a guy sodomizing me, I was glad I was down to my last hurdle with three days remaining. It wasn’t my lucky day as Bob spotted me. He obviously didn’t have a life since he was always at the hotel.

He caught me before I could make it to the elevators and said, “I’ve been waiting for your call, I really have a lot to delivery, if you know what I mean. I certainly wouldn’t want to have to make a call ‘cause you’re dodging me,” and he chuckles. I had to think quickly so I said, “Not dodging you, I’ve just been out visiting with friends. Maybe I can order something when I wake up.” Then to set his mind into overload, I leaned into him and whispered, “Have you ever done anal? I’ve got an itch and maybe you can scratch it,” and I squeeze his crotch. Obviously caught off guard, Bob stutters, “I’ll try anything once,” which indicated to me he was an anal virgin.

Making it to my room, I jump in the shower before heading to bed. As I cleaned up and went to bed, I marveled at the transition to a complete submissive I had just taken. It was a side of me I never imagined. Of course, I never imagined myself as a girl either. Not surprisingly, I slept until mid-afternoon. I was hungry and knew ordering room service would put me face to face with the inept lover I had sought to avoid. Having not been successful, I decided to take a different approach and set his ass up. I ordered a big meal with the works, as well as a bottle of wine. If my plan worked, he would be paying for it for several weeks.

A few minutes before it was to be delivered, I stripped down to just panties and slipped on a bathrobe. As a bit of insurance, I dabbed a little desensitizer on my asshole. If things worked as I suspected, it would be totally unnecessary, but when dealing with a pervert, you can’t be too cautious. I set the bottle of lubricant on the side table for easy access. Promptly at 3 there was a knock on the door. As I opened it, Bob pushed the cart in grinning like the cat that ate the canary. The bulge in his pants was an indication that he had been thinking about it since I planted the seed. His impatience showed as he pushed the cart to the table and blurted out, “C’mon let’s do it. I am so horny for your ass.” I said, “Whoa, let’s at least have a glass of wine and set the mood. Something like this can’t be rushed, and I let the robe fall open slightly so that Bob can see my panties. Bob looked at me completely befuddled and said, “Oh, Okay,” and starts fumbling with opening the wine. I smiled as it was apparent that he was as inept with alcohol as he was with sex. After he poured two glasses, I suggested we sit on the couch and enjoy them. I sat in such a manner that he could glimpse at my boobs through the gap in the robe. His erection seemed to become more pronounced as we sipped and chatted. I poured us each another half glass as I could see the frustration building on his face. I didn’t want to push my luck to the point that he took charge so I set my hand on his leg, rubbing his thigh to increase his excitement and began to explain slowly and seductively how this was to work. I said, “Now anal sex must be started slowly. You can’t just force your cock in or it won’t be enjoyable. What we can do is get naked and get on the bed. To insure easy penetration, I’m gonna put some lubricant on your nice hard cock. I have to coat it from top to bottom if you want to put it all the way into my hot, tight ass. Once it’s ready, I will straddle you lap and guide it in. Since my ass is a little small, I’ll just put the head in and get use to its size. Then I’ll ever so slowly take more and more until I have it all. If you’re okay with it inside, then I’ll start twerking my ass and milk you.”

BOB: “But I thought anal was done doggie-style.”

LILY: “We can switch to that after a few minutes. Once I’m use to your size, you can turn me over and guide that stiff cock deep into me and watch it sliding in and out of my backdoor.”

My plan was working to the tee. I could see a fuzziness in his actions as the wine impacted him and the small wet spot on his pants belied the emittance of pre-cum from his erection. I stand taking him by the hand and lead him to the bedroom. As he wrestles to strip off his clothes, I seductively slide the bathrobe off and lie down on the bed.

BOB: “What about your panties?”

LILY: “In time. I want you to relish the thought of my nice tight ass still hidden,” and I roll onto my tummy, slapping my ass cheek.

Shedding his underwear, Bob climbs onto the bed, his cock bouncing wildly in the air, the tip glistening from arousal. As he laid next to me, I retrieved the bottle of lube. As I grasp his cock in my left hand and began to drizzle a small amount on the head, I said, “You’ll feel a slight warming sensation. That’s to be expected. Now just relax and get ready to enjoy.” I glided my left hand over the tip capturing some of the lube and began spreading it on the shaft. Dripping sufficient emollient onto his shaft my hand deftly slid up and down several times, increasing how tightly I squeezed each time. Suddenly I hear, “Oh shit. Stop. Stop.” As I look up at Bob’s face, it is slightly contorted. I can feel his cock twitch as I stroke up the shaft again and as he tries to pull away, his cum starts oozing out the tip and down across my fingers and his shaft. Acting surprised, I said, “Oh shit, you were supposed to wait until you were inside me.” My hand continued squeezing his cock as I stroked another time and more of his jism trickled out.

Putting him on the defensive: “Now what are we to do?” You weren’t supposed to cum. What happened?”

Bob stammering, “I don’t know, it just happened. Your hand felt so good with the lube, it just started cumming.”

As his cock rapidly deflated, I was confident he wasn’t going to get back up anytime soon.

Keeping him from gaining composure I continue, “Well shit. Why didn’t you warn me? Now look at the sheets, you better get a maid to come change them. I can’t sleep in a wet spot. You had your fun, what about me?”

BOB: “Maybe we can do it later.”

LILY: “I don’t know. You must have wanted it awful bad. We’ll have to see when the next chance will be.”

Bob regaining a small measure of swagger, “We will do it again. And next time, I’ll apply the lube to insure you don’t make me cum.”

LILY: “I didn’t make you cum. I only stroked it a couple times.”

BOB: “Yeah but that lube was super slick and it caused me to cum.”

LILY: “Okay, Next time you apply it. I just had hopes of you doing me this afternoon.”

BOB: “Yeah I’ll do it next time. Or maybe I’ll make you take it without lube.”

LILY: “I don’t think so. That’s liable to hurt.”

BOB: “It’ll only hurt if your ass is tight. My dick will split it open.”

Internally I was laughing as I knew there would not be another opportunity for him to get in my ass or any other orifice for that matter. I retrieved a wet washcloth and tossing it to him said “you better get cleaned up and get a maid up here later this afternoon. Next time, you better plan on staying up longer.”

BOB: “You’re just lucky I slipped up. Otherwise, I was gonna pound that tight ass of yours every which way I could.”

After he dressed and left, I enjoyed my dinner and the remainder of the wine, smiling that I had popped his cork so easily. I was glad Olivia had mentioned how the lube was prone to cause some guys to cum so easily. As I ate, I took time to assess my situation.

My mind was all over the place with the events. I was into my fourth day as a woman and had knocked off 4 of the 5 conditions. I had quite enjoyed my time with Vickie and sex with Steve almost went unnoticed because I was still active with Vickie. My session with Olivia was amazing and one I would be thrilled to continue. I figured with the cream and lube she gave me, I could tolerate the last task. She certainly had opened my ass to the pleasures of anal. I was grossed out by Bob’s session but had extracted some revenge and was plotting the rest. And what was gonna happen when I finished? Would I suddenly change back to a guy? What was Tatyana going to do to me if I succeed? What if I fail? Enough worries. It was Saturday and tonight would be my best shot at finishing as the clubs would be packed. I just had to swallow my male ego and take some unsuspecting guy to bed.

I headed out at dusk. I dressed in what I hoped was mildly provocative but not slutty. I knew of a couple locations that had dancing and considered them the best opportunity for assessing the field of candidates. I knew what I didn’t want as a partner; some macho jerk that might take control and alter the plans for his own gratification; some whimp that might pop like Bob before entry or some guy that might be playing multiple girls and leave with someone else. What I didn’t know was who I did want. I had never tried sizing a guy up for sex so I was a little lost. The first location was packed so I passed figuring I could always return. The second was a much better fit as it was busy but not full. There was a general mix of couples and singles. I ordered a drink and staked out a small table from which I could see most the activities. I briefly pondered the option of hooking up with a couple. I would be oblivious to the guy if I was busy with his partner but then how do you ask a chick ‘Hey can I get your guy to fuck my ass while I do you?’ I decided to let things take their course. As the first hour drug on, I had opportunity to dance with a few guys and was even bold enough to ask one sitting with a girl. Actually, I asked her if she would mind if I danced with her man. She was cool with it but obviously not going to let it go far. As the second hour broke and I was nursing my third drink, a pair of guys walked in. As they found a table, I perceived the taller one was the other’s wingman. I watched the shorter guy swing and miss on a couple attempts at meeting ladies. He definitely had the better looks and was far more outgoing but was too much like the clichés. The tall one just seemed to be there and not really add much to the activities. I decided he might be a good target. I strolled over and asked if he would like to dance. The short one was as surprised as the tall one but we headed to the dance floor. As we moved, I learned his name was Jerry and the other guy was Tim. They were roommates and worked offshore for two week shifts. They would be leaving again Sunday evening and wanted to hit the clubs one last time. Over the course of the next 90 minutes, I danced with Tim, Jerry and a couple others. Figuring Jerry as my best option, I kept him the busiest. After the two bought a couple more rounds, I thought I would roll the dice and see what will happen. It was still early enough that if Jerry bailed, I could consider alternatives but late enough that we could get to his place. I picked a song that warranted me dancing close in front of him and drug him onto the floor without asking. As the music played, I would move my butt closer to him. Since he didn’t back away, my next move was to brush the front of his jeans with my ass. Again, there was no retraction by him. Knowing the song was more than half over, I grabbed his hands and pulled him in close. As he pressed against me, I gyrated my ass against his crotch. He obviously enjoyed that as he started pressing back, almost with thrusts. I smiled to myself as I felt he was more than willing. After the song, we returned to the table. Tim used the next song to troll for a hook-up while we caught our breath.

Leaning toward Jerry so that he could hear me, he did the same. I asked, “You like my ass? You didn’t seem to mind us dancing.”

JERRY: “Absolutely, you have a nice tight butt.”

LILY: “Well that nice tight butt has an itch that I think you could scratch.”

Jerry with a slightly confused look on his face said “What?”

Repeating myself: “How would you like to scratch that ass?” and I ran my hand up his thigh.

Jerry with a big grin crossing his face: “Would I ever.”

LILY: “You understand I’m talking anal. Have you ever done a girl’s ass?”

JERRY: “Yes and no. I’ve heard about it from guys and seen it on porn but you’d be my first.”

LILY: “If you want to try, let’s get out of here and I’ll lay down the rules for you.”

Jerry pulling back a little: “Rules?”

LILY: “You’ll understand, just makes it more enjoyable for both. Let me visit the Ladies Room real quick and you can let Tim know you and I are heading to your place and not to disturb us if he brings a girl home.”

I slip into a stall in the Ladies Room and dab a little of Olivia’s desensitizing cream on my hole. My finger felt good moving around the hole and I took an opportunity to press it in some. I wondered if I was actually starting to enjoy anal sex regardless of my history. I met Jerry at the door and he said he was ready.

As we step outside, I ask: “What did Tim say?”

JERRY: “He said go for it, He only hoped that he would find someone too. Do you mind a short trolley ride? I told Tim he could take the car.”

LILY: “No problem.”

As we rode the trolley to the apartment, I explained, “The rules are simple. Since this is your first time and I don’t want either of us injured, you do things at my pace. Unless I indicate otherwise, I am gonna ride you, kinda cowgirl style. I apply the lube to your cock so that I know it’s covered. If you get excited and start thrusting hard into me, I’ll sit down on you until you settle back down. I just don’t want you rearranging anything inside.”

Jerry laughed: “Anything you say boss. Just be gentle with me, I’m a virgin.”

Looking at him surprised, “A virgin?”

JERRY: “No, I meant for anal.” And we both laughed.

Arriving at his place I notice it’s relatively neat for a guys’ apartment. Some luggage is already lining one wall where they are readying their return to work. After Jerry offered me a drink and I declined, I took his hand and whispered, “Are you as horny as I am?”

Jerry needed no further encouragement as he led me down the hallway toward the bedrooms. Pointing to the left, he said, “That’s Tim’s room.” Turning to the right at the end of the hall we walk into his bedroom. I start loosening my blouse and shed it onto a chair. Jerry steps up to me and starts fondling my breasts through the thin material of the bra. When he leaned down to kiss me, I offered my neck as I was still not quite there with kissing a guy. After freeing my tits from the bra, his hands slid down and started unbuttoning my jeans. As I started reciprocating with his jeans, a sudden shiver went through me. What would happen if he was endowed comparable to his height? There was no way I could take a footlong schlong up my ass regardless of the lubricant and desensitizer. His hands moved inside my jeans and around back to cup my ass, pushing my pants off my bum so they fell to my knees. His squeeze on my cheeks was very soft. While not squeezing his butt cheeks as he did mine, my hands worked around him pushing his jeans down. We sat on the edge of the bed long enough to shed all our clothes except my panties and his briefs. By the bulge in his shorts, I was not sure what size cock I was about to mount so I beckoned him to lay out on the bed. I retrieved my jar of lubricant, dimmed the lights and knelt down on the bed by his knees. Swallowing hard, I reached up, grabbed the sides of his shorts and pulled them down revealing his erection. While it was not fully up, it looked to be eight or so inches and of medium girth. I took it in my hand and started stroking him. His cock didn’t grow much in length but it definitely grew harder. I poured a little lube into my hand and slowly moved my hand up and down coating him, the entire time watching his face to guard against anything premature.

Satisfied that he was well coated, I sat back and pointing my legs toward him, slid my panties off giving him a full view of my pussy. I was confident my ass was desensitized as it had been tingling for some time from the numbness.

As I swung my leg over him such that I was kneeling above his cock while facing him. I smiled and asked, “Are you ready for this?”

JERRY: “Oh yes. You are so beautiful and your ass is so nice looking.”

LILY: “Remember the rules. I want this to be good for you.”

I lower to the point that the tip starts spreading my cheeks and I move it to align with my asshole. Slowly I lean back and feel it sink in a little. Adjusting a little, I take more into me. The lube is making the penetration easy and after a little effort, I have taken his entire length inside. As I settle down on him, I hear a low moan from Jerry. For the next several minutes, I rock up and down on his shaft and he occasionally pushes up into me.

Looking up at me, Jerry asks, “Can I do it from behind you?”

LILY: “Do you mean on all fours with you kneeling behind me or laying on the edge of the bed?”

JERRY: “Kneeling if that’s OK.”

I rose up slowly, allowing his cock to vacate my ass. My ass almost felt strange not being full of cock. As he rose to his knees, I got on my hands and knees facing the end of the bed. Looking over my shoulder at him as he eased his cock into my hole I whispered, “Remember the rules. We’ll take this nice and easy.”

JERRY: “You got it. I just love the feel of your tight little ass. I don’t know how much longer I’ll be able to hold out.”

LILY: “Babe, just let it go when ready.”

As Jerry rocks in and out, I lower my head and close my eyes as I try to focus on anything but the fact that I have a guy’s cock in my ass. My mind is drifting between thinking like a girl enjoying the experience and a guy whose previous butt-play was limited to a girl pegging me in role reversal play. Suddenly I become aware of someone in the room. Raising my head, I am confronted by Tim completely naked and with his dick in his hand, slowly stroking it.

TIM: “Mmm, I was wondering if you were gonna look up. Why don’t you suck on this while my man Jerry finishes in your hot little ass?”

LILY: “No way, I didn’t agree to any tag team event.”

TIM: “Oh hell Lily, haven’t you heard the term Bro’s before Ho’s. Jerry and I agreed to share if one gets lucky and the other strikes out. More time Jerry is getting seconds but he hit the jackpot tonight.”

LILY: “I’m no Ho and I only agreed to come home with Jerry. Had I known, we wouldn’t be here right now.”

Tim stepping closer to the bed: “I didn’t mean it that way. And well you’re here now and my cock needs your mouth.”

LILY: “The hell you say!”

Tim pushing his dick to my lips: “Just stop talking and start sucking. I’m not gonna cum in your mouth.”

This entire time, Jerry is pumping my ass using long deep stokes. As the head touches my lips, I initially don’t open but then Jerry pushed in a little harder and as I lurched forward, Tim’s cock enters my mouth.

TIM: “That’s more like. Just make it good and hard in that hot mouth of yours.”

The two develop a rhythm such that I am the one moving between the two cocks. As Jerry pushes my hips allowing his cock to slide out, I am forced to take more of Tim’s cock into my mouth. When Jerry pulls my ass onto his dick, Tim’s cock retreats from my mouth.

After a couple minutes of this, Jerry’s pattern changes to short, rapid thrusts. At the same time Tim takes his cock out of my mouth. I can only guess that Jerry is getting close. My hunch was right as he suddenly shoves his dick all the way into me and holds against me. I can feel his dick spasming and shoot a load of cum into me. He then repeats the deep, hard thrust a couple more times as he empties himself into me. After a few moments, Jerry’s erection is softening and he slowly withdraws from my tight hole. I look back over my shoulder as he is climbing off the bed. Initially I didn’t see Tim, but looking over the other side, I spy him just as he grabs my left ankle. With a hard jerk, Tim pulls me toward the side of the bed where he is standing. Not able to be well balanced while on all fours on the bed, my leg is pulled out from under me and I fall awkwardly flat on the bed. Tim grabs my other ankle and pulls me to the edge, with my legs draped toward the floor and me on my tummy. I start to roll over to face him when he suddenly lays atop me.

Wiggling beneath his weight I protest, “What the hell are you doing?”

As he puts his hand between me and him grabbing his erection he says, “I get sloppy seconds tonight.”

LILY: “Oh no you don’t. You aren’t fucking me too.”

TIM: “Lay still and enjoy. I told you we were gonna share you.”

LILY: “No, please don’t. You don’t have any lubrication. It won’t go in.”

Tim managing to locate my hole with the tip of his dick said, “I don’t need any lube, Jerry split you wide. I’m only a little bigger so relax.”

As he starts his entry I continue protesting, “No, it will hurt me. You need something on it.”

Fortunately, the desensitizer was still effective and there was a measure of lube around the hole as it had built up during Jerry’s session. Tim advanced his cock its full length before resting atop me. His penetration wasn’t as deep as Jerry but he was a little wider. Forcing my legs further apart with his, Tim started humping fast and hard into my ass. I can only groan as Tim’s actions are much harsher than Jerry’s.

As he squeezed my ass cheeks he proclaims, “Oh you have such a fine ass. Tight, hot and just begging for a cock.”

Realizing I have little choice I now hope to get into a more comfortable position. I ask, “Would you like to do it like Jerry? Or maybe another position?”

TIM: “No, no. I got you right how I want you. As tight as you are, it won’t take me long but I’m gonna fuck you hard until I explode.”

In hopes of expediting his orgasm, I start urging him on at the he risk of more pain in my ass, “Come on baby, give it all to me. Fill my ass with you hot cum. You can do it; pound my backdoor with that hard cock.” I simultaneously was squeezing my muscles around his dick to milk it. Whether it was anything I did or just his time, I don’t know. But about a minute more he is humping me franticly and saying, “Oh shit, I’m cumming. I’m cumming.” And then I feel his hot seed entering my ass and mixing with Jerry’s. As he slows, I tighten my ass in an effort to eject his softening cock. Once out, he falls on the bed next to me breathing hard.

TIM: “See that wasn’t so bad. Jerry opened you and I closed.”

LILY: “You’re an SOB. I wouldn’t have done you except you forced it. Jerry was the one I wanted.”

TIM: “Well you got double for your money.”

I rolled away from Tim and headed to the bathroom. Locking the door behind me, I sit on the toilet to let the loads drain out. In reality, as a girl I actually enjoyed both ass fuckings and was quite aroused. Knowing I had completed the five tasks, I also know I will be restored as a male. I would probably include more ass play as a guy but limit it to either self-pleasure, with a kinky girl or maybe a Domme. As I think about things, my hand drifts down between my legs and I slip my middle finger into my pussy. I was amazed at my wetness and started rubbing myself with increasing pressure. In moments, I am in full masturbation mode. One hand is rubbing my clit while the middle finger of the other is pumping into my pussy. As I start cumming, my ass is squeezing out the globs of sperm. As my pleasure subsides, I lick my hand clean. After washing up my sex holes, I return to the bedroom to dress. Only Jerry is lying there and I ask, “So where’s the bastard that forced himself on me?”

JERRY: “I’m sorry, but usually I’m the one that gets second fiddle and I never force it. Most the times the girl’s willing to do two guys.

LILY: “Had you asked, I might have been willing to as well. But there’s something about a cock being shoved into your mouth or ass.”

JERRY: “I’m sorry. Is there anything I can do for you?”

LILY: “No, I’ll just go. And for what it’s worth, you were the better lover.”

Jerry smiling: “Thanks.”

I caught the trolley back to the French Quarter and chuckled to myself about what a relief it was that I didn’t immediately revert back to a guy after completing the five tasks. Walking the few blocks back to the hotel, I passed the bar where I met Tatyana. When I see her from the door, I step inside. When she spies me, she comes over, gives me a hug and a kiss and says, “I didn’t think I would see you this quick but you are resourceful. Why don’t you come by my place tomorrow evening and we can visit.”

LILY: “Sure. You free all evening.”

TATYANA: “For you babe, I’ll be free all night.”

LILY: “I’ll see you later then.”

After a quick kiss good night, I make it to the hotel. As usual the lobby is buzzing with the return of the late-night revelers. Fortunately I don’t see Bob but decide it’s time to turn the tables on him. Taking a chance that I catch Bob at a time he is busy or better not at the hotel, I ask the desk clerk if I can leave him a message. Smiling, she hands me some paper and a small envelope. Knowing he is full of himself, I leave a long note saying,

Don’t know if we will get back together, maybe Monday.

I still have that itch that you can deliver the cure on.

Met a girl the other day that would really like to meet you.

I think you would enjoy meeting her too.

Her names Olivia and she works at the adult boutique in the 600 block of St. Charles

She would love to see your sexual prowess and likely invite to her home.

Your room service hottie



I slept in Sunday not having anything left to accomplish. I thought about visiting Olivia again but didn’t want to get tied up, so to speak, and miss my rendezvous with Tatyana. Instead, I decided a nice, long soak in the tub was warranted. As I enjoyed the warm water and fragrant bath crystals, I let my hands drift over my body. I was amazed at how my body felt as a woman. I touched different areas such as my breasts, applying different pressures, touches, and squeezed, marveling at how enjoyable it was and piquing my arousal. Forgoing touching my womanhood, I let my fingers play with my rosebud. I enjoyed rubbing my finger across it as it flexed. Turning my finger inward, I pressed just the tip into my tight hole. I retreated and then pressed several times with each press advancing further into my ass. With about an inch in, I paused, squeezing my muscles around the index. It felt almost as if my muscles were drawing it in deeper rather than expelling my finger. Before long I was wiggling the entire length inside my butt. I slid the finger in and out wiggling it every direction loving the sensation it presented to my ass. I was getting more turned on by the minute. It was only a matter of time before my hands made it to my vagina. I explored it tenderly, feeling the folds of my labia, tracing the hood discretely hiding my clit, and exposing my clit to the warm water. I knew my touching would create a hunger within my pussy but in a cruel self-inflicted punishment, I resisted immediate self-satisfaction for the sake of slow investigation. Eventually resistance was futile. One hand began rubbing my clitoris feverishly while the other pumped two fingers into my pussy. The water was splashing everywhere but I was oblivious as I rocketed toward an orgasm. When it peaked, I clinched my legs together, holding my fingers deep within. As it subsided, I relaxed and laid in the tub letting the water soak my skin. If this is how women enjoy bathes alone, I can understand why they take some long ones.

I slipped out for a late lunch and returned to my room early evening to gather the clothing I had taken from Tatyana’s place. I was not sure what the evening was to hold and the waiting was beginning to play on my mind. Was Tatyana going to snap her fingers and turn me back into a guy? Was she going to deceive me and leave me as a woman? The original transformation took many hours, was that going to be the case tonight? The only thing I was reasonably sure of was that Tatyana and I would have more sex regardless of whether I was a man or woman. With that happy thought on my mind, as I dressed for what I assumed would be my last time as a girl, I opted to go bra and panty-less. At about 9:30 I head out. Passing through the lobby, I spy Bob. As a flirt to further set him up, I hiked one side of my skirt up giving him a brief glimpse of my bare ass.

I arrived at Tatyana’s place about 10 and headed inside. She sat reclined on the couch in a flowing black housecoat of very flimsy material. As she stands, I notice she is wearing nothing more than a black G-string. She comes to me and framing my face with her hands she says, “You are such a beautiful woman,” and then kisses me deeply. We kiss long and tenderly as we explore each other’s mouths. After our passionate kiss she takes my hand and leads me to where she had been sitting. She asks that I recount all the escapades I had enjoyed. The surprising aspect of the discussion was that she knew everyone’s names. While I had already told her about my threesome with Vickie and Steve, I was mystified how she knew about the other four. She expressed her sympathy after hearing about Tim’s intrusion but I dismissed it as incidental. I even shared with her that I had grown to find anal quite enjoyable between what Olivia, Jerry and Tim had done. She merely smiled through the conversation. After I concluded Tatyana stood and extended her hand to me. Taking her hand I rise and she proceeds down the hall. As she led us into her bedroom where the large antique bed stood, she turned to me and said, “Come make love to me on the bed.”

LILY: “I would enjoy that.”

Tatyana slowly undressed me, what little I had on and after dropping the housecoat stretched out on the bed. The next hour was spent in tender and passionate love-making. We alternated giving oral pleasure to each other and on a couple occasions simultaneously. Our biggest orgasms came in what was our last act of passion. With our arms and legs entangled and lips against each other’s, I moved my thigh to press against her pussy and started pushing against her, rubbing her vagina. Realizing what I was doing, she raised her thigh into a similar position against me. As we rocked on our sides, I was alternately pushing my pussy against her leg for stimulation and pushing my leg to stimulate her. I felt the orgasm start deep within me and as I began to cum, I was humping wildly against Tatyana and grasping her ass. As I was moaning in pleasure, she also started cumming and reacted in the same wild frenzy. We held each other tightly as the glow of satisfaction filled us.

She whispers, “Sleep with me tonight. I want to hold you close,” and kisses my cheeks.

LILY: “Yes, I want to be with you.”

As we cuddle, spooning with her behind me, I feel her arms gently hugging me and her soft breath on the back of my neck. As I am drifting into slumber, I hear a distant clock chime what I suspect was midnight. While I was in the fog that one experiences between awake and asleep, I feel the gentle insertion of her penis into my pussy. It is so gentle it doesn’t disturb me. Before nodding off and despite Tatyana lying perfectly still, I feel the penis sliding in and out as it starts pumping cum into my pussy, the warmth spreading into my nether region.

I do not know how long I was asleep but when I woke it was still dark. Tatyana was still cuddled up spooning with me but the position was reversed. Not only was I snuggled against her back, but nestled between her legs and pressing against her vagina lips was what felt like my erect penis. With my right hand draped over her side, I gently started to slide it down toward her crotch, hoping not to disturb her in the process. My goal was to determine if I did in fact have an erection squeezed between her legs. As I am slowly passing her stomach, she intertwines the fingers of her right hand with mine. I whisper, ‘I’m sorry if I disturbed you.” Without responding, she guides my hand down to her pussy. As our hands reach their destination, she presses my hand against her soft folds. Using her middle finger against mine, she pushes me into her crack. I can feel the distinct knob of her clitoris and she starts rubbing it with my finger. After a bit, Tatyana moved my hand beyond her pussy to the tip of the penis held between her legs. As I touch the bulbous head, I am thrilled to realize it is my cock. Using my hand, I press my cock between her vaginal lips and can feel her sexual heat.

Tatyana moans a little and whispers, “I want you inside me.”

As she opens her legs, I adjust my hips slightly allowing me to enter her pussy. She is very wet and I encounter no resistance. We slowly rock back and forth as I enjoy the restoration of my dick. My right hand returns to rub her clit only to find her hand already doing it.

Looking over her shoulder she says, “I want you to fuck me and fuck me hard. I want to do it in several positions but I want you to hold out until you’re on top.”

ME: “I will do my best. Just tell me how you want it.”

TATYANA: “Right now, just give it to me fast and hard.”

I adjust my angle a little more and start thrusting hard and deep into her. With each penetration, I feel her soft butt cheeks press against my loins. I am pumping her as fast as one can laying on one’s side and have replaced her hand with mine stroking her clit. After a couple minutes she had a small orgasm. She then asks that I let her up. As I withdraw from her, she rolls over facing me and then pushes me onto my back.

Smiling at me she asks, “You want a little taste before I go for a ride?”

ME: “Absolutely!”

Tatyana moves to straddle my face and as she gets over my mouth, I grab her butt cheeks and pull her pussy to my tongue. I plunge my tongue in as deep as I can, licking anything it contacts. Her wetness is sweet and plentiful. After an ever so brief moment, she raises up from my mouth and proclaims “No offence but I want something bigger and deeper than just your tongue.”

As she is moving down my body I respond, “Understood. Take whatever you want of me.”

Positioning her pussy directly over my erection, she lowers down moaning as it fills her. Tatyana starts bouncing up and down, riding me in true cowgirl fashion. With every penetration, I sink completely in.

As she increases her motion, she moans, “Oh yes, fuck me. Fuck me deep.”

After a bit, she grows weary and lays down on my chest. She uses a twerking motion to continue riding my cock. By spreading her legs with mine, I am now able to participate in the intercourse and in unison I am thrusting rapidly into her as she pushes down on my rod. I grab her ass and accentuate my thrusts by pushing her down in such a manner as to press her clit against my cock while I slide it into her. Within a couple minutes, Tatyana’s body gets rigid and she is pressing her pussy against my shaft as she experiences a second orgasm. As it washes over her, she collapses on me lying still with only her pussy squeezing my throbbing cock. I let her catch her breath and then cup her butt cheeks and start to resume the motion that just got her off.

She whispers, “Shhh. I want you to take me from behind. I want you giving me every inch.”

ME: “I’d love to.”

As she rolled off me and onto her back, my cock slides out and glistens from the cum she has coated it with. She rolls onto her tummy and pulls her legs up under her while I move to position myself behind her. With her upper torso still lying on the bed, her butt sticks up higher in the air. I lean forward and kiss her butt cheek as I move to align my dick with her pussy. I can see the globs of her juices that have accumulated on her labia. Her pussy hole is slightly open and I put the head inside. When I hear her say, “Yes, do it baby,” I lean into her and slide every inch deep inside. I hold it there wiggling a little against her butt cheeks and then commence to fucking her with long hard strokes. I grab her hips to keep from pulling completely out and as a little balance. We are in a frenzy as I alternate from the long, hard strokes to the faster short plunges. The only thing I hear from her are moans when I am shoving my dick into her. Tiring a little, I bend such that I am pressing against her back. To assist me, she raises up onto all fours and we are humping like a pair of animals. Tatyana is so wet, I am feeling virtually no friction and am not getting close to exploding. When I feel her hands fondling my ball sack, I know she is playing with herself as well.

With an unexpected suddenness, she pulls off my shaft and lays flat on the bed. I almost fall on her as my body was in mid-thrust. She rolls over onto her back and with me still kneeling where she had left me, she looks at me and says, “I want you to eat me and then make love to me.”

As I move down a little on the bed, Tatyana spreads her legs before me. Her labia open slightly allowing me to see her vaginal opening. Her pussy and the surrounding area reflect the wetness from her accumulated juices. I lower my head between her legs and start licking up the cream. I do so very slow and tenderly, methodically cleaning up between every fold. I am not trying to induce another orgasm in Tatyana but rather just providing her pleasure while keeping her arousal level up. Her heavy breathing and low moans confirm I am achieving my objective. The air is thick with the smell of sex and sweat. After tonguing the entire area, I raise up on my knees, looking to Tatyana for an indication as to how she wants me to proceed. As she extends her arms beckoning me to move atop her, I anticipate the final act is before us. I slowly move to a position where my erection is between her legs and the head is just inside her pussy. As I lay down in her arms, my cock sinks slowly into her. This is not going to be the wild, frenzied sex we partook minutes before. Rather, this was going to be truly gentle love making. Our hips slowly grind against each other while we are kissing each other on the lips, cheeks, necks and shoulders. Every move is done with a passion. For the first time this night, I can feel my orgasm building from deep inside. I try maintaining a slow steady pace but as Tatyana builds toward an orgasm, her breathing becomes more rapid, she wraps her legs around me and she is pressing her vagina against my cock in a more deliberate manner. I unconsciously start increasing the tempo, pushing hard against her button. She has not yet reached her peak when I feel the sudden onset of my orgasm. Thrusting deep and pressing hard against her, I jettison my first blast of cum deep inside her. This is followed by several repeated withdrawals and then deep thrusts as I empty all my sperm into her. She is pressing back against every thrust trying to climax so I continue the pumping despite having filled her. As she cums, she lets out a little shriek and wraps her arms tightly around me, sinking her nails into my flesh. I continue to push my cock into her until she relaxes at which time I roll to my side, still with my semi-rigid member in her vagina.

Smiling at me as she frames my cheeks with her hands, she whispers, “Welcome to my bed.”

I kiss her softly as I slowly extract myself from her sex. A few moments later she starts getting out of the bed and announces she is going to shower.

To be continued
1 comments

Russell FultzReport 

2021-05-29 00:07:30
Great story I've enjoyed reading the 4 chapters I hope you keep writing more chapters of this story. Thank you slick98

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