Unexpected Sexperience With Unexpected Woman
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An Unexpected Attraction free porn video
“You want to fuck me, don’t you?”
What the fuck? I stopped in my tracks.
I was coming back from the men’s room, heading back to the pool tables where I shot pool with a mix of regular and semi-regular guys every Wednesday night.
There in front of me was Stella, one of the waitresses, hand on her hip looking up at me like a real smart ass.
Stella, while not super-hot, was very pretty, with long dirty-blonde hair down to her shoulder blades. This wasn’t “Hooters,” just your friendly neighborhood bowling alley with some pool tables, so her body wasn’t exactly on display, but she definitely filled out her uniform T-shirt well. She had a small nose stud, which isn’t normally my thing, but on her it worked.
“So what if I did?” I answered after a brief pause.
“Go for it!” she said and went bouncing off to pick up an order.
I was stunned. Stella was certainly attractive enough; it being two years since my divorce, I was certainly horny enough, but beyond the friendly flirting that any waitress does with most customers, I never had given her any real thought as a potential date.
My game was off the rest of the night, as every time Stella would go by my table she would give me a smile and a wink. I wondered if anyone else saw it, but the other guys didn’t seem to notice anything out of the ordinary.
The following week I was coming back from the men’s room when she accosted me again, forcing me up against the wall.
She leaned in and whispered in my ear, “Did you think about what I said?” grabbed my crotch and hustled away before I could regain my senses.
I was the last in our group to leave, and when I got outside I saw Stella taking a smoke break.
“You know you really shouldn’t smoke,” I said to her.
She just shrugged her shoulders and said, “Whatever.”
“You shouldn’t keep teasing me, either. Someday I might try to take you up on it, and then what would you do?”
She hesitated just a moment, tossed her cigarette aside, pulled my head close and laid a hot kiss on me, forcing her tongue into my mouth.
I don’t know how long we kissed, but I was panting for breath when she broke the kiss. That was when she hit me with her curve ball.
“I’m a T-girl,” she said. “Do you know what that is?
“Do you mean you’re a guy?” I asked incredulously. “No way! Prove it!”
She took my hand and placed in on her crotch, and I’ll be fucked but I could feel something there.
I then grabbed one of her boobs.
“So, how do you explain this,” I said defiantly.
“Hormone injections,” she said.
“I ... I can’t deal with this right now,” I said, and hurried to my car.
I stayed away for a couple of weeks while I dealt with my feelings.
Stella was certainly attractive, and other normal circumstances I would have been after her like a Bloodhound, but these were far from normal circumstances.
I was completely straight, with zero interest in having sex with a guy, but Stella still turned me on. Despite what I felt between her legs, she didn’t seem like a guy. I was really conflicted when I went back to shoot pool a few weeks later.
Things were a bit cool between us for a bit, even the other guys commented on it, but we soon returned to our usual flirting.
Nothing more was said, but I couldn’t get what happened out of my mind. On the one hand, she was a guy; on the other hand, I was really attracted to her; on the other hand, she was a guy ... and on and on I went.
I finally bit the bullet and asked her out for ... I guess you’d have to call it a date.
I had been on many first dates, but I had never been as nervous as I was when I approached Stella’s front door.
Stella must have been just as anxious as I was, as she nearly yanked the door open as soon as I rang the bell.
We leaned in for a quick hug and pressed our cheeks together. Was it my imagination or did her cheek feel a little scratchy? Wouldn’t the hormones have taken care of that?
My mind was spinning, and Stella seemed to sense my confusion.
“Are you okay, Ralph?” she asked. “Do you want to reschedule?”
“No, no,” I replied, “This is just all so new to me, I’m just so unsure of myself.”
“Ralph, it’s okay, relax. Just treat this like any other first date where we’re trying to get to know each other.”
“Except that there is a lot that I already do know about you, and you have to admit that it’s not something that happens every day.”
“I do understand, Ralph. I won’t hold it against you if you want to cancel, but why don’t we go out to dinner and just let things take care of themselves. Maybe you’ll think that I’m a loser, maybe I’ll decide that you’re obnoxious, maybe we’ll hit it off. No preconceptions, no expectations.”
“No expectations,” I agreed. I took her arm and led her to my car, opened her door and helped her in.
We went to a restaurant on the other side of town. We weren’t embarrassed or anything, we just didn’t want any gossip, especially if things didn’t work out.
“Stella,” I started, “I really enjoy our friendship, and don’t want to do anything to risk that.”
“Me either, Ralph,” she said. “I feel the same way. We’re both adults, going into this with our eyes wide open. I’m pretty sure we’ll be okay.”
With that out of the way, we settled into the normal conversation that any couple has on a date. I actually found myself forgetting about our unique situation, and started thinking about Stella as I would any other date.
We ended the date with a friendly hug, a chaste kiss on the cheek and a promise for more dates to come.
Nobody at my pool nights seemed to suspect any changes in our relationship, and yes, that’s what it was, a relationship, as we saw each other once or twice a week.
We were nowhere near being intimate, though we did end our dates necking in the car and with a tender kiss on the lips at her door.
After several weeks I could see Stella was getting a little anxious, and I realized that pretty soon I was going to have to fish or cut bait.
Finally, I was close to a decision, but I needed to have a serious talk with Stella before I could finalize it.
In all of our dates I had never entered Stella’s home, but when I took her home that night, I uttered the immortal words.
“Stella, we need to talk.”
Tears filled her eyes, and I used my thumb to wipe them away.
“No,” I said, “It’s not that, or at least I don’t think so.”
She sniffled a bit, nodded and opened her door. I followed her in, and as we sat on the couch we turned slightly towards each other and I took her hands in mine.
I said, “Stella, I’m very attracted to you, but, I’m very straight and have no interest in sex with a guy, and I don’t know what kind of a future there is for us in any sort of an intimate relationship.”
“I understand, Ralph,” she said, “but maybe we could work something out?”
“The problem as I see it, Stella, is I could maybe close my eyes and shall we say, accept certain sexual favors from you, but I know that I could never reciprocate, and I don’t feel that is fair to you.”
“Why don’t you let me decide what’s fair for me?”
Well, that put the ball squarely in my court. Could I see myself having sex with a guy, even if from my perspective it wasn’t “gay” sex?
“Stella, I think I’m going to need a little time to process this.”
“I understand, Ralph, but please don’t take too long. I’ve developed strong feelings for you, but I don’t know how much longer I can stand to remain in this state of limbo.”
With that she walked me to the door, we kissed and I made my way home with my mind going around like a merry-go-round. It’s a good thing there wasn’t much traffic or I might not have made it home.
I skipped pool again, but by the following Wednesday I had made my decision, and could only hope that I wasn’t too late.
Stella saw me as I walked in and raised her eyebrows in question. I gave her a small smile, nodded and went to join my buddies.
At the end of the night I lingered until all the other guys had left, and looked for Stella.
“Stella, I think I want to give us a try. Can I come over Saturday night?”
Her eyes brimmed with tears as she nodded yes.
“Come over around six, I’ll make dinner.”
I resisted the urge to give her a hug and hurried out to my car.
I was pretty useless at work for the rest of the week, and as nervous as a high schooler going to his Senior Prom as I knocked on her door, holding a bouquet of flowers.
When she opened the door, her eyes glowed at the sight of the flowers. She gave me a quick peck on the cheek and took the flowers to put in a vase. She put them on the table as I sat down, then she ran into the kitchen to get the food.
She was an excellent cook, and we made small talk while we ate. I helped her clear the table and load the dishwasher, then we went to sit on the couch for the talk that might change the course of our lives.
That is, I thought we were going to be talking, but as soon as we sat down Stella laid a big kiss on me, attacking my mouth with a vengeance.
We had kissed many times during our make out sessions, but this was completely different. This was Stella taking possession, saying this is my man.
Stella was kissing down my neck, rubbing my neck and unbuttoning my shirt, kissing all over my chest, and she sucked and nibbled at my nipples. I had never considered my nipples as much of an erogenous zone, but the way Stella went at them had my cock straining in my jeans.
Stella noticed and began rubbing my crotch, then started unbuckling my belt.
“Do you really want to go there?” I asked maybe the dumbest question in history.
“Just lie back and relax. I’m a big girl, I know what I’m doing.”
Being no fool, I did just that and watched while she unzipped me, pulled down my pants and briefs at once, freeing my raging hard-on.
Stella kissed and licked up one side of my cock and down the other before gently sucking on the head. As she took more and more of it into her mouth I was so excited that I was afraid that I was going to shoot too soon, and tried to think of Roseanne naked to calm myself down.
After a few moments of gently sucking on my cock, she gradually took me deeper and deeper until I was lodged in her throat and her nose was buried in my pubic hair. Her tongue was stroking my cock while her throat was massaging the head.
I was momentarily amazed at her control over her gag reflex, but soon felt myself getting close.
“Stella,” I managed to gasp out, “I ... I’m gonna come.”
She just smiled around my cock as I shot my load into her mouth. After she swallowed she gently cleaned off my cock, then laid her head on my shoulder and smiled sweetly up at me.
My ex-wife had never let me come in her mouth, so I wasn’t sure what to expect when Stella came up to kiss me, but I didn’t really notice anything, maybe because most went right down her throat.
While I felt guilty not being willing to reciprocate, Stella seemed content as she snuggled up against me and my hand gently stroked her breast through her shirt.
We continued to see each other on a regular basis. I certainly enjoyed her blow jobs, and she did seem to enjoy giving me pleasure, but it still upset my sense of fairness.
After a couple of dates I removed her shirt and bra, and any thought of her being a man slid to the back of my mind. She had firm breasts, maybe a small “B” with prominent nipples.
They were very sensitive, and I was able to give her small orgasms simply by playing with them and sucking on them, but it actually made me feel even more guilty.
One night as she came down from an orgasm, she snuggled under my arm as my hand toyed with her nipple, sending small tremors through her body.
“Did you ever consider having the surgery?” I asked.
She hesitated for just a moment.
“When I first decided that I identified as a woman, and would live my life as a woman, I thought about it; I decided against it. I did go through the counseling that’s required, just in case I decided to do it.”
“May I ask why you decided against the surgery?”
She looked away for a minute, then gave me a sideways glance with a small smile.
“I like having a dick.”
I was a little taken aback, and had to struggle a bit to get the image of Stella naked, playing with her tits while jerking off out of my mind, but that put that topic to bed, at least for a while
I was conflicted. I felt a deep attraction to Stella, and not just on a physical level, and I wanted to be able to love her as she deserved to be loved, but I just couldn’t wrap my head around the fact that she had a dick. I would never be able to make love to her as a man should make love to his woman.
Stella seemed a little nervous.
“There is something else that we could do,” she said softly.
I must have been really slow on the uptake.
“Huh?” I said.
“We, uh, you, could use my ass.”
I guess most people are grossed out by anal sex, but I think that most men are at least curious about it. I was no exception, but I was very hesitant. While I was certainly curious, it wasn’t anything that I felt I was missing. I also wasn’t sure if this was something that Stella really wanted, or was just willing to do, thinking that I might want it.
“Stella, why are you asking this? Is this something that you want?”
She just shifted nervously in her seat.
“Have you ever done it before?” I asked.
She pulled her head up quickly.
“N ... No,” she said softly, shaking her head.
While I was touched by her offer, I decided to refuse. To be totally honest, I was afraid that the sight of her penis would shatter my illusion of her being all woman.
“It’s an interesting offer, Stella, but I don’t think we’re in the right place for that. I don’t think that we’d be doing it for the right reasons.”
Stella seemed relieved as she nodded her agreement.
That left us at the status quo, which wasn’t exactly an unpleasant place to be. We dated, made out, and did just about everything we could do without going below her waist.
We continued as we were for several months, but soon we were at an impasse. While we both enjoyed what we had, I was at the stage in my life that I was seriously considering re-marriage and raising a family, and I could tell that Stella was feeling something, also.
We were once again enjoying the calm after a sex, or was it love, session, when Stella dropped her bombshell.
“What would you think of me having the surgery?”
“I think that you should have it because YOU want it, you shouldn’t do it because you think that I want you to have it.”
I wanted so badly to tell her that if she had the surgery that we would be together, and it might have even been true. I also knew that if she didn’t truly want it for herself, that she might come to resent me for it, and I was selfish enough to not want to risk what we had.
“Ralph, I think I’m going to need some time to myself. I don’t mean to imply that you’re pressuring me in any way, but I need to think things over without any distractions.”
“I understand, Stella,” I said, “Take the time you need. You’re worth waiting for.”
She threw her arms around my neck and I held her tight as she buried her face in my shoulder. I felt her tears on my neck and pushed her away gently.
I tilted her chin up and kissed her gently on her lips.
“Don’t worry, Babe,” I said, “Everything will be okay.”
She snuffled and nodded, a little unsurely it seemed, gave me a peck on the lips and saw me to the door.
When she closed the door behind me I leaned back heavily, still not sure if I was doing the right thing.
I knew Stella belonged to a trans support group, and expected that at least some of her time would be spent with them. I could only hope that she would make the right decision for both herself and us.
I didn’t hear from her for the next couple of weeks, and couldn’t help but notice that she wasn’t working Wednesday nights when my guys and I shot pool. I didn’t want to draw any special attention by asking about her absence, I assumed that she simply swapped off with another one of the girls.
Two weeks to the day after our talk, Stella called, said she wanted to see me.
“Is it good news or bad news?” I asked.
“I think it’s better that we talk in person,” Stella said.
That didn’t exactly ease my mind, but she wouldn’t budge, so I got myself together and went over to Stella’s, prepared for the worst.
We each got a cup of coffee and sat on her couch. There was a pregnant pause, then Stella spoke.
“Ralph, I have some good news, and some hopefully not so bad news.”
My curiosity piqued, I motioned for her to continue.
“The good news is that I’ve decided to have the sex reassignment surgery.”
I brightened a bit at that news.
“Okay, that’s the ‘good news.’ What’s the not so good news?”
“I know you said that I should only do it if I want it for myself, and I do want it, but I also want it for you...”
“That sounds a little contradictory to me,” I said.
“Let me try to explain. It is true that if we had never met or got involved, I probably never would have considered it, and been quite happy going along as I had been.”
“That’s what I don’t want! I don’t want you doing it for me!”
“I’m not doing it for you, I’m doing it for me.”
“Now I’m totally confused,” I said.
“Let me try to explain,” she said again. “Now, before you object, I realize that what we’re talking about is more extreme, but what if we lived in different parts of the country, and if I wanted to be with you I had to move?”
“That’s not nearly the same thing!”
“Maybe we were of different faiths, and I had to convert if we were to continue our relationship.”
“That’s closer, but you’re talking major surgery here.”
“I know, but I love you and want to be with you, and I’m willing ... no, I want to do this for you, for us.”
My head was swimming. If it was strictly up to me, I certainly wanted her to do it, but my concerns remained. What if she grew to resent having to do it, what if we had a fight and she threw it in my face.
Although Stella had already gone through the counseling, enough time had gone by that her counselor wanted to speak to her again, particularly since she had come to a new decision. The counselor wanted to speak to me, also.
While the counselor had some concerns about Stella’s reasons for wanting the surgery, they didn’t rise to the level of her objecting to it.
Her questioning of me was primarily to reassure herself that I hadn’t pressured Stella in any way. She was actually pleased when I expressed my own concerns about Stella’s reasons, and eased my conscience when she explained that while this was more extreme, that Stella’s analogies to moving and religious conversion were quite valid, that one partner often had to make some sacrifice in order to be with the other.
With the counselor’s approval in hand, we had some preparations to make. Stella’s job wouldn’t allow her the kind of leave she would need, so she would have to quit her job.
Conveniently, as it turned out, her lease was up, so we decided that she would move in with me. My bedrooms were on the second floor, but I had a den on the first floor, and I rented a bed to allow her to stay on the first floor while she recovered from the surgery.
As the date of her surgery approached, she gave her notice, and we spent many nights just cuddling on the couch as she dealt with her fears about just about everything: the pain, how our lives would change, how she would feel about herself.
I tried to comfort her as best as I could, but I shared many of the same fears myself.
Soon the day came for her surgery, and we rode to the hospital in a nervous silence.
Our wait was very short before she was taken to be prepped for surgery, and I only had time for a brief hug.
“Don’t worry, Stella, everything will be okay, I’ll be here when you get out of surgery.”
She gave me a tearful nod and a quick kiss before letting the nurse lead her away.
It was the longest six hours I had ever spent. The nurses tried to get me to go home, that they would call me when Stella was out of surgery, but I wouldn’t hear of it. She was going through all of this for me, the least that I could do was be here for her.
I was awakened from a snooze by one of the nurses.
“The surgery went well. She’s in recovery, you can see her for just a few minutes until she’s moved to a regular room.”
“Thank you,” I said as I shook myself to finish waking up, then followed her to see Stella.
“Just a few minutes,” the nurse said, then left me at the door.
Stella looked like she was asleep, but stirred with a groan as I took her hand in both of mine.
“How are you feeling? I asked.
“Like I’ve been kicked in the nuts,” she said with a small laugh that brought on a fresh moan.
“Should I get the nurse?”
“No, I’ll be all right. It only hurts when I laugh,” she said with a weak smile. “Thank you for being here.”
“Where else could I be?”
“Well, you could be in the shower, you reek!” she said, holding back a laugh. “Why don’t you go home, have a bite to eat and clean up. Hopefully I’ll be in a regular room by then.”
It was hard to tear myself away, but she was right; I stunk. I gave her a quick kiss and left for home.
Sure enough, by the time I got back she was in a regular room, sitting up and looking more alert.
“Are you feeling better?”
“Yes, still a little sore. It still feels weird, even with the bandages it feels empty between my legs. I’m sure I’ll get used to it.”
She must have seen my face drop.
“Don’t blame yourself, Ralph. I knew what I was getting into. This is what I wanted. It’s just going to take some getting used to.”
She insisted on calling for the nurse to help her to use the bathroom. I volunteered, but she wasn’t ready for me to see her “there” yet.
After a few days I was allowed to take Stella home and set her up in her temporary room. While I was allowed to help her to the bathroom, she insisted that she could take care of herself.
“I’m going to see it sooner or later, Stella,” I said through the bathroom door.
“Yes, I know, but it’s still very irritated right now. I don’t want that to be the first image you have of the new me.”
I heard her moan.
“Are you sure you’re okay?” I asked.
“Yes, Ralph, the doctor assured me that some irritation is normal and should fade away in just a few days.”
I had my doubts and concerns, but there was nothing I could do but wait.
A week after she came home she had a follow-up appointment with her surgeon, but refused to tell me what she said, and was very pensive all the way home.
Dinner was very quiet, all of my attempts to draw what the doctor said out of her were met with noncommittal answers and shy smiles.
We watched a little TV before Stella gave a big yawn,
“Ralph, I’m tired, if you don’t mind I’m going to make it an early night.”
“Of course, Honey, I’ll probably crash soon, too,” I said as Stella gave me a tender kiss, went to her room and closed the door.
After a few minutes I went up to bed. I was feeling a little frustration. We hadn’t had any sort of sex since she went into the hospital, first, obviously, because she was in the hospital, then because she wasn’t feeling comfortable. I had masturbated a couple of times and figured it was time to take myself in hand again.
I had dimmed the lights a bit, and was making myself comfortable when the bedroom door opened and I saw a vision of loveliness silhouetted by the hall light.
Stella was wearing a skimpy baby-doll nightgown with the tiniest panties I had ever seen.
“The doctor cleared me for light sexual activity today. We should be very cautious as far as intercourse goes, but we can do as much as I’m comfortable with.”
With that she dropped the nightgown to the floor, and was about to lower her panties when I stopped her.
“No, Baby,” I said grinning, “I want to unwrap my present myself.”
Stella grinned even wider than I did and gave her best impression of a stripper walk as she came over and climbed onto the bed, straddling my legs as she knelt down, took my face in her hands and kissed me with a passion that I never knew we were missing.
I broke the kiss so that I could shift my attention to her breasts and nipples, rubbing, kissing and sucking on them as she threw her head back in pleasure.
We could put off the moment of truth no longer. I lifted her off my lap and lay her on her back beside me.
I straddled her legs, took a deep breath and reached for the top of her panties. Stella looked nervous, but also had a look of anticipation as I drew her panties down over her hips exposing her pussy.
I’m not sure what I was expecting, but the first thought that ran through my mind was that I was going to have to send her surgeon some flowers. I know that different men have different ideas about what makes a pretty pussy, but for me, Stella’s was absolutely beautiful. She had to shave for the procedure, and had obviously kept it that way, except for a small landing strip above her mons.
Her pussy was still a little pink, but didn’t seem irritated, maybe it was just the flush of her arousal. I finished removing her panties, spread her legs and immediately took her new pussy for a test drive with my lips and tongue. She must have been on a hair-trigger because she came almost immediately, clamping her thighs against my ears.
When she came down enough to release my head I began a more leisurely exploration of our new playground, to Stella’s apparent delight.
Stella still didn’t feel up to trying intercourse, but she immediately put her talented mouth to work relieving my tension, bringing me to two very satisfying orgasms.
After changing the bed linen and cleaning up she climbed into bed with me and snuggled into my side, resting her head on my chest.
“I love you, Ralph,” she said, “Thank you for being so patient with me.”
“I love you, too, Stella, and I’m the one who should be thanking you. I know that was a difficult decision for you to make, and I want to spend the rest of my life making sure that you don’t regret it.”
It took Stella a few moments to process what I had just said.
“The rest of your life?” she said, sitting bolt upright. “Are you saying what I think you’re saying?”
I reached into the nightstand drawer and retrieved the ring box. I opened it to show her the ring inside.
“Stella, after my divorce I never thought I would find love again, especially under such unusual circumstances,” I said with a wry smile. “Then you came into my life, and I can’t imagine it without you in it by my side. Would you do me the honor of being my wife?”
She couldn’t speak, just nodded her head crazily with a huge grin on her face, holding her left hand out for me to put the ring on her finger.
We settled back down, and she couldn’t take her eyes off the ring until sleep finally overtook her.
I woke up to the most pleasant sensation of her mouth on my cock, but as soon as she saw that I was awake she stopped.
“Please don’t stop on my account,” I said grinning, but Stella sat up looking a little apprehensive.
“I ... I want you to make love to me,” she said.
“Last night you said that you weren’t ready. You don’t have to do this just because I asked you to marry me.”
“I know I don’t have to. I want to. I can’t say that I’m not nervous, and please be gentle with me.”
She reached into her nightstand and pulled out a bottle of lube.
“My doctor gave me this. It’s uncertain how much lubrication I will produce naturally, but this will help.”
I nodded and took the bottle from her, but I didn’t use it right away. I began again with her breasts before lowering my mouth to her pussy. When I felt that she was as warmed up as she was going to get, I put some lube on my hand and began to gently rub her pussy, gradually inserting one finger, working it in and out and around. I got more lube and added a second finger, and she began writhing around. I applied some lube to my still hard cock, got between her legs and aimed my cock at her entrance,
“Are you sure you’re ready for this?” I asked.
Mckenna
- 27.05.2021
- 31
- 0
