After Hours at Self Checkout Ch. 02

The drive to Tammy's house was nerve-wracking. As I sat in the passenger seat my palms were literally sweating. The fact that I was seduced and had sex with a complete stranger at my job left me in shock, but that fact I was driving with her to her house to get to know her better was really getting to me. After we pulled out my job's parking lot we sat in the car in silence. As the street lights passed across the front side windshield, the front of the car briefly illuminated, allowing us to make quick glances at each other. This more so happened to me due her having to keep her eyes on the road, but I did catch her shift her eyes in my direction and shot quick smiles. Her smile left me kind of nervous because I could sense her lustful energy she was sending my way. So part of me felt bad that I was getting so worked up in front of a beautiful woman who just gave me such an amazing experience, so let myself sink into the seat and let out a deep breath.

"Hey are you okay over there?" She asked as she stopped the car at a red light and looked at me.

"You seem very tense. Am I making you nervous? If I am, you can talk to me about it, or should I just take you home?" she said while staring to ramble.

"No, I said I wanted to get to know you better, but I would be lying if I said I wasn't nervous. Honestly I am just new to all this." I said in a more softer voice.

"Wait, are you a virg-" she asked before I cut her off.

"Yes, I am a virgin and also I have never had a girlfriend." I blurted out in embarrassment.

"Oh, that explains a lot." she said, looking a little sad as she pulled into a gated community with condominiums.

I looked around at the condos and immediately thought this place must be very upscale. Then we turned onto a road with a dead end and pulled into a condo garage on the left side of the street. Tammy had taken out a remote from her glove compartment and pressed the button opening the garage door in front of us to allow us to slide in. The motion sensors in the garage flicked on the lights illuminating the dark garage. The garage was pretty clean minus a couple small shelves lined up on the outer walls with very few boxes and goods. On the left side of the garage was an elevated door leading to the condo itself. She parked and turned the car off, but she didn't immediately unlock the doors so we could get out of the car. We simply sat in the car letting the tension between us build up after I told her about my virginity.

"Darrel, I don't want to make you do things you don't want to, but if you spend the night I assure you I will try my best to make sure you are as comfortable as possible." she said, looking me in the eyes with sincerity.

My heart felt hot and heavy as she told me this. The nervousness I had been feeling all this time started melting away being replaced with longing to be intimate with her. I unbuckled my seat belt and laid my head on her lap and started using my hands to rub her crotch. As I rubbed I could feel her erection becoming more pronounced in her dress. I looked up at her face with warm, lustful eyes.

"Thank you for being so caring. I will try my best to repay you for your kindness." I said, hiking her dress down her legs so I can get access to her panties. "First, by loving your lovely dick." pulling her panties aside so that her erect dick could present itself to me.

And present itself it did. As the bindings of her panties were gone and her cock sprung from her crotch hitting me in the face. I immediately grabbed her cock at the base to keep it steady.

"Sorry about that, honey. You just got me so excited. Just watching the lust on your face as you hold my dick so eagerly is honestly a dream come true." said Tammy reaching her hand to the back of my head. "Please wrap your pretty lips around my dick. I need to feel the warmth of your mouth!" she moaned while rubbing the back of my head.

"With pleasure, Tammy." I said while diving my lips on her dick.

As my lips enveloped her dick I could feel a genuine connection between us forming. My body was getting hot and tingly. My dick was getting hard. It just felt so right. It didn't take me long to realize that Tammy had felt the same connection because she started to rub the back of my head and moan loudly.

"Oh, my god! Your mouth is driving me crazy! It feels so different from last time. It feels like your mouth is making love to my dick." she screamed as she tilted her head back to get lost in the sensations I was giving to her body. "Oh, my god! I am getting so hot! It feels so weird, but it feels so good." she said, pulling her hand from the back of my head to grab her plump tits which were heaving up and down due to how excited she was.

I was definitely sucking her dick with all my effort. I was letting spit collect in my mouth and occasionally gagging myself on her to enhance her sensations. To be honest I was emulating all the blowjob techniques I saw from porn. It really helped. My best and most favorite part of the blowjob was letting my mouth overflow with spit letting it drench her dick. It made speeding up and stroking the rest of her length with my hand so much easier. I looked up at her as I continued my sucking and saw an amazing sight. Tammy had zipped down the top half of her dress to let out her big tits and was playing with her erect nipples as she breathed heavily.

"Darrel, no one has ever gotten me this worked up before. This is more than just hitting the right spots. This feeling is overwhelming my body. I have a feeling you are feeling it too, are you?" she said in between gasps.

"I am feeling hot and heavy as well. My dick is so hard." I said after pulling off of her dick. "What do you think this is?" I ask looking up at her with a little concern in my voice.

"I have a feeling it's love, Darrel." she said, grabbing my face and pulling it close to her own so that our lips smashed together into a kiss.

I was so stunned by her kiss that my body froze causing me to go limp. The weird thing is that I couldn't deny that what I was feeling was love as well. But some part of me felt there was more to this. I wanted to find out more about my feelings for Tammy and her feelings for me. It didn't take long for me to regain control of my body and wrap my arms around Tammy's waist so I could safely explore this kiss. Tammy eventually pushed her tongue to my lips as an invitation into my mouth. I quickly opened my mouth letting my tongue collide with hers' upon entrance. This caused us both to moan in unison. This war of tongues went on for a while causing us both to get light headed.

"Okay, let's calm down real quick. I am getting a little out of it from our kiss. And secondly, I want to get into my house where it's more comfortable." She said after breaking away from our kiss leaving me longing for more.

After a quick breather Tammy quickly used the remote to close the garage door before unlocking the doors.

"Let's get in the house. I don't know how much longer I can keep my hands off of you." she said in a rushed voice. She grabbed her purse that was in the back seat and opened her side to get out of the car.

I followed shortly, keeping my eyes on Tammy's erect penis and huge tits which were still exposed. We made our way to the garage door that led into the house. Tammy made quick work with the door key before grabbing me by my hand leading me inside. The first thing I came to is a professional kitchen, with gas burners and a restaurant oven. In the middle of her kitchen was a dining platform with stools on each side and hanging from the wall was a circular hanging rack for pots and pans. She had a decently sized two sided sink one bigger than the other.

"Nice kitchen." I quickly mentioned as she dragged me into a nearby hallway that led to her living room.

"Thanks, I will give you a tour of the house later. Right now I just need you on my couch now!" she said pushing me on to the largest of three couches.

She pounced after me, enveloping her body with mine. I could feel her large breast press against my chest and her cock grinding into my crouch. She wasted no time kissing me all over my face and neck while her hands roamed across my body to search for any erogenous zones.

"Ahh... That feels so nice." I moaned as her fingers went up my shirt and caressed my nipples.

"Oh, my god, I am loving your sensitive nipples, but I really want to take care of your little friend down here." she said making her way down my body to my pants.

"Can I take my shirt off, please? You have me really hot from all this." I asked, looking at her softly in her eyes.

"Of course you can. I want to see your cute body as I give you pleasure down here." she said, making quick work of my zipper while pulling my pants down to my knees.

I quickly took off my shirt so I could continue looking down at Tammy as she decided what she was going to do with my erection. At this point my dick was bulging from my underwear leaving a wet spot. Tammy pushed her finger to the spot trying to get a little bit on her finger. She caressed my shaft hoping to push more pre-cum on her finger through the fabric.

"I think that's enough." said Tammy observing the amount of pre-cum she had on her finger. She brought her finger to my lips presenting me with my pre-cum. "Now lick my finger clean." she ordered.

I wasted no time putting her finger into my mouth and sucking her clean, the taste of my pre-cum on her finger didn't taste weird. As I continued sucking her finger, my dick was pulsing inside the fabric.

"Your pulsing! You must really like the taste of your cum. That's a good thing because I like it when my lovers swallow their rewards." She said, messaging my pulsing bulge.

Her other hand was still wrapped around my dick trying to milk more on to her hand. I moaned really in response hoping she would feed me more, but she had other plans as she moved her drenched hand to the opening of my asshole. She wasted no time lathering my hole to get it slick and wet.

"I love the idea of using your own cum to lube your ass!" she said with a lustful tone.

I responded with a sharp moan causing me to lean up so that her breasts were lying across my back while she continued to rub her fingers around my hole.

"I want you to relax. I am going to eat this pretty ass of yours then I am going to finger you." she whispered with her lips just above my ear.

In no time she moved her body off of mine making me miss her body enveloping me and her soft breasts pressing into my back. She had repositioned herself so that her face was in between my open cheeks. I tried to relax and calm myself down as I tired to prepare myself for the sensations that were about to wash over me. It didn't take very long for me to feel two hands spreading my ass cheeks apart and something soft, long, and spongy gliding across my glazed hole. The sensation was so intense I couldn't hold in my moan.

"Oh, my gosh, that feels so weird, but it feels so good!!!"

She responded by simply slapping on my ass cheeks causing me to jump. She briefly moved away from my hole to respond to me

"I am glad you love this because honestly I can't wait to have you wrapped around my cock." she said before returning back.

The reality that she was planning to slide her 9 inches of meat into my tight virgin ass filled me up with many conflicting emotions, fear, anxiety, and excitement. She sensed my emotions as my asshole twitched against her tongue. In response she decided to go one step further and slip her tongue into my ass which sent my body into a frenzy of sensations.

"Ohhhhhhh, my god, your tongue it feels so wet inside me!!!" I moaned loudly, arching my back on the couch so that my butt was high in the air.

Upon entering this position she quickly pulled away from my wet hole to inspect her work. My ass crack felt drenched; I didn't realize it at first but as she was licking my butthole she let all her excess saliva drip down to my balls so that my whole crack was covered in saliva.

"God, you look wonderful in this position. Let me go to my room and get a few things to get you ready for our main course." she said, rushing to a hallway on the opposite side of the kitchen entrance.

I was still feeling very nervous, but the thought have having sex with this woman was overriding my nerves. This was honestly a dream come true. All the porn I watched of trans girls fucking dudes in their asses had really left an impression on me. It made me want to experience the same thing.

She eventually returned with a couple things: a large white beach towel, a large bottle of liquid lube, and a syringe. When I saw the syringe I looked towards her with my ass still in the air and my lower half still on the couch with a look of confusion.

"I just want to make sure I can get into your tight ass without hurting you. So I am gonna be using this syringe to make sure you're lubed inside and out. I want to make sure you feel no pain. Remember, I told you in the car was going to make you feel as comfortable as I could tonight if you came here." she said, laying out her gear to the side of her.

The first thing she did was instruct me to get off the couch for a second so she can drape the towel across the couch. After she did that I got back on the couch on all fours with my upper body raised ups so that I was level with my ass. I then felt something warm and slippery being poured all over my ass. I quickly turned to observe her pouring baby oil over my ass.

"I want you to be glistening while I fuck you." she said with a crazed look in her eyes.

I hadn't noticed before, but the way she was breathing seems labored as if she was very excited. She also had this weird sense of enjoyment on her face that for some reason put the hairs on the back of my neck up.

"Are you okay, honey?" she said seductively as she messaged the oil into my butt.

I paused for a minute to really consider if telling her how I felt was appropriate for the current situation. When I didn't respond immediately shifted her slippery hands to my shaft and started slowly massaging my dick and balls in oils. This change elicited a quick response which was more honest then I wanted it to be at the time.

"I am okay... but I just get a feeling that there is more to why you are excited to be doing this with me?" I said with a slight moan in my voice.

She didn't respond immediately which was odd at first, but then I heard the clicking of a cap and something wet and cold drenching my exposed asshole. Then I felt like one of her fingers massaging my anal ring with what I assumed was lube for about a couple seconds before I felt my hole being spread around her finger.

"Oh, my gosh!!!" I moaned loudly as I tensed up really quickly in response to the intruder in my asshole.

"Oh, I love the way you sound when I am inside you." she said slide her finger in and out of my hole.

The nerves in my body were exploding from the sensations of her finger going and out of my ass. I made a small moan to let her know she was making me feel great. When she saw I was getting used to one finger, she slipped a second finger in my ass eliciting another strong moan from me.

"That was a nice one, but I wanna see what you sound like when I hit your magic spot-" she said seductively as he let her fingers curve downwards to what I would come to find was my prostate.

My voice lept upward causing my moan to sound high-pitched. This caught Tammy by surprise and brought a new wave of arousal from my voice.

"Oh, my god, you actually sounded like a girl. You don't know how much excitement you sent to my dick with that moan. My mind is racing with the kind of things I want to do with you If I can get you to moan like that."

She kept on hitting the spot, continually causing me to elicit more strong girly moans. And with each moan the excitement her breathing kept on climbing. The sexual waves of pleasure crashing into me made me hyper aware of my body's reactions. Besides the muscle twitching I was doing, I felt a steady stream of pre-cum start leaking from my penis. If my lower body made any sudden movement the pre-cum ended up on the inner part of my thighs.

"God, I need to be inside you. I can't take it anymore!!!!" she said, pulling her finger out of my hole.

The shock of not having her finger in my ass brought me back from my bliss so I could catch her in the process of drenching her 9 inch cock in a bottle of lube. She also filled the large medical syringe full of lube and stuffed the nozzle in my ass eliciting a quick moan from me.

"I want you to moan real loud as I fill your hole with lube, okay?" she said holding the syringe steady.

"Oka- ohhhhhhhh!!!!" I said before being cut off by the feeling of what felt like a stream entering into my body. "Oh, my god! That feels so weird to have so much fluid flowing inside!" I moaned letting my lower body crash into the couch putting my body into an arch.

When she finished administering the lube she fingered my hole one more time to message and get it all in and out of my hole before replacing her fingers with the head of her hot 9 inch dick.

"Normally I would tease my toys before entering them, but I need to be in you now. So I want you to breathe in and out and try to relax." she said while starting to apply slow pressure to my hole.

As I breathed I could feel the head of her cock slowly widening my hole. What I also felt was a burning sensation that caused me to scream out.

"Oh, my god, it's burning!"

"Just keep breathing it will pass." she tried to reassure me.

The burning did stop as my hole closed up around the large head of her cock. The pain was still there but it wasn't getting any worse.

"I am going to slowly sink myself into your cute little body." Tammy said with a seductive, yet possessive tone.

The sensation her dick was giving me was causing my head to get light-headed and my tongue to roll out of my mouth. I was making very small moans as her dick slid slowly into my ass. This slow process went on until her hip met my butt and she had completely bottomed out in my ass.

"This is so lovely, Darrel. I am completely inside you. Can you feel my length inside you? Can you feel my dick flexing? " She asked as she lowered her body across my back so that she could talk into my ear.

I was so overwhelmed that all I could do was moan my response with each flex of her dick in my hole.

"Yes, I can feel.. you... it feels... good!!!" I said in between waves of pleasure.

"Good. Because now that I have you where I want you, I wanna answer that question: if there is more to this and to be honest I have wanted you for a year." said Tammy letting her voice become a little excited.

A sense of concern hit me in response to what she said causing me to try to respond.

"What do you mean?" I asked with labored breath.

"I mean that I fell in love with you the first day I saw you at that self check out a year ago. I was scared to talk to you because I didn't want to scare you away. So I simply would avoid self checkout every day. I didn't want to face myself not mustering enough courage to talk to you." she said in a soft, loving tone.

The way how she said it warmed my heart and removed any unease I had.

"I didn't know, I am sorry If I did anything to make myself unapproachable " I said, finally being able to make out a complete sentence as my body got used to having her 9 inch lovestick inside of it.

"It's not your fault, but I want to tell you now that I have you. I am not gonna let go!!!" She screamed with lustful passion as she wrapped around my midsection and flexed her dick.

"Oh, you are hitting that spot again!" I warned.

"Oh, I know I want you to feel my excitement. But I also want to be up front with you. I can go a little overboard, so please let me release my love for you. With your permission let me take you." She asked.