Ryan becomes Jennifer Pt. 03

The next morning he asked me how far did I want to go. I knew exactly what he meant and I had thought about this too. In fact, if he had tried last night I probably would've given in.

He told me how badly he wanted to be my first but he also wanted to make sure I was ready for this. He explained my butt is too tight and I'll need a little training.

He gave me a bag and told me to follow the instructions then take a shower. So after we had coffee I did as he said. In the bathroom I found a box inside the bag and it was an enema to cleanse myself. I followed the instructions to the letter after relieving myself and it actually felt nice squirting the cool liquid up inside me. Then I released this and climbed in the shower. After washing my hair and shaving my legs I was rinsing off when Charles got in the shower with me.

At first I was little embarrassed having him see me with my boy parts out but he never really looked down there. He just pulled me into his arms and we kissed under the water.

I washed him lathering up a luffa then wash his barrel chest and shoulders, his arms. Then he turned and I washed his huge back and down his to butt and behind his legs. Then he turned around and since I was on my knees I washed his legs and his groin taking a long time with his cock and balls.

I stroked his soft cock while it's all covered in soap as he begins to get hard in my hand. He turns just enough to let the shower rinse him completely and I take his dick in my mouth and suck on the head slow and sensually keeping eye contact with him.

"You are so beautiful Jenni. And you like giving head, huh?"

"Mmhmmm." I moan.

"It's time to start your training, okay."

I nod with a mouthful of cock.

"Stand up baby, let's get dressed. I have something for you."

I do as he says and follow him out of the shower. As we're drying off in the bathroom he turns me to face the vanity mirror standing directly behind me placing kisses all over my shoulders and neck sending waves of chills throughout my body. In a small way I feel so vulnerable and timid as I'm not all girly. Yet when I look in the mirror with my hair wet, I still have a very feminine appearance.

The chills don't go away as his kisses continue down my back, all the way down. I have no idea what is about to happen but Charles is on his knees behind me now kissing my ass cheeks while running his hands up and down my legs.

Then his hands slide up between my thighs reaching my ass and he spreads my cheeks apart. I'm nervous yet this feels so hot I'm loving this attention he's giving my ass now.

Then I feel his warm moist tongue run from just behind my boy parts up my crack and over my hole I nearly hit the roof! He held me firm as his tongue licked all around my entrance while I went insane.

"Ohhhh!" I cried out bent over the vanity as his tongue drove inside me. I could feel myself having an orgasm and I wanted more.

I was somewhere between heaven and the clouds when his finger slipped inside me. It was a severe change of feeling yet with him still kissing and licking I offered myself to him even more by pushing back on this intrusion.

Then he had two fingers inside me as they slowly worked little circles inside me and I felt myself begin to tremble all over.

Suddenly his fingers retreated and I hear a clicking sound followed by him telling me to relax myself and my sphincter.

This was much easier said than done as I had been on my tip toes and bent all the way over the vanity holding on tightly. So I took a deep calming breath and I do relax.

Then I feel my ass being ripped apart in a brief moment of searing pain then it was gone!

"All set baby," Charles exclaims as he stood up behind me and pulled me upright hugging me from behind.

"All set?" I ask shakily.

"Yes, and I have a gift for you."

"Wait, what's happening here? What's inside me?" I ask looking at our reflection in the mirror.

"It's a butt plug and that one is the starter. Later we will move you up to the next one and then you should be ready."

I leaned back against Charles smiling because I did want this and I wanted this with him.

"C'mon sweetie, I have something else for you in the bedroom."

There are three outfits laid out on the bed, a cute lavender mini dress, a red floral mini skirt and a puffy white off the shoulder crop top and a two piece black mini skirt set. Each outfit also has its set of shoes too. The first had four inch open toe shiny white pumps, the second red floral wedges and the last four inch black sandals with black ties that go around the ankles.

He told me I can choose what to wear underneath.

"What's wrong? Are you okay? You don't like the outfits?" He asks me a bit concerned.

"Oh yes, I'm fine and I love these. It just feels a little strange with this in me."

"Oh, I see." He turns me to face him holding onto my shoulders, "I'm told you'll enjoy it more as you get used to it and with the heels on."

"Okay, I'll be fine. It's just different is all."

Walking actually felt incredibly erotic and sitting was a whole different adventure. I chose the red floral mini skirt and white top outfit first with a lace white thong.

I dressed while Charles went out and made coffee and I loved this mini skirt! It was very short with adjustable strings at each side of the hemline and back zip up. The top was just as cute with a tie string in front, long puffy sleeves and floral lace trim all around the bodice.

I really adored the wedges as the were very comfortable to wear and really pushed up my butt which, as Charles has said, felt so sexy as I walked into the dining area where he was waiting.

He stood up with the biggest smile on his face and embraced me kissing my forehead then standing back at arm's length.

"Damn sweetie! You look amazing."

"Thank you." I say a bit shyly.

"How would you feel about a day out seeing the sights?"

"I'd like that."

From the moment we left the plug drove me crazy with lust! Walking in four inch high wedges seemed to really emphasize the sensation and I've been walking in heels for a couple weeks now. But this really made my butt stick out or so it seemed.

And sitting! Are you kidding me?!

Every chance I got I would touch him, kiss him even grope his crotch and Charles didn't stop me.

We had taken a drive up the Blue Ridge Parkway and we pulled into an overlook with a beautiful view in every direction.

I took the opportunity to give Charles a quick l blowjob in the car even with people in the vicinity. I was rewarded with a huge load from him and then we went on our way.

It was late in the afternoon back at my house and he ordered sushi while I changed outfits this time to the cute lavender mini dress.

It has short sleeves that are very tiny, off the shoulders with a tie string bodice. There are also tie strings just above the hem of the thighs. It's cotton and very thin and feels so soft and sexy. Under this I wore a soft pink thong and four inch white platform heels.

After touching up my makeup and hair I went back to the living room with Charles.

The night was all blissful for me as we made out on the couch and later in the bedroom I again gave him a long loving blowjob.

In the morning the routine was almost like the day before, douche, shower insert a bigger plug. Only this day did take an unexpected turn.

To start the day I wore a pretty floral yellow summer dress and flat sandals. He was taking me to some vineyard and seemed fairly excited about this. Then his phone rang while we were having coffee and he got extremely angry while talking to whoever was on with him. He said this was outrageous, incredibly inconsiderate and very unprofessional. Then he hung up and looked at me with very sad eyes.

He took my hand in his and said, "I'm so sorry Jenni. One of our clients in Seattle made a huge mistake and I have to go fix it."

"Hey it's okay. We can continue when you return."

"I will be a couple days hopefully I'll be back Tuesday or Wednesday."

"Then we can get together?"

"Yes." He says with a kiss.

I spent the afternoon cleaning an already clean house. I had changed into blue denim short shorts and a tank top and I kept the plug in while I worked. It was such a turn on.

I hadn't looked at the website for a couple days so I decided to have a look. Again there were lots of messages and it took awhile to go through them when I saw David had sent me several messages.

In response to all his requests to at least speak on the phone I sent him my number again and told I'm available whenever.

It wasn't long before my phone rang and it was David.

"Hello?"

"Jennifer?"

"Yes."

"It's Dave."

"Hi Dave."

"Hi, is this really you? You actually sound like a girl too."

I giggle, "thank you."

"How do you do that with your voice?"

"I had an injury and it kind of altered my voice."

"I'm sorry about the injury part but I really like how you sound. It's very uh, sexy?"

Again I giggled, "thank you."

"My pleasure. How's it going?"

"It's going well. Kind of bored but otherwise I'm okay. How about you?"

"I'm really bored to be honest with you. I was hoping we could meet up or something? I hope that's not to forward."

"What did you have in mind?"

"A hotel? My place?"

"Oh, that's pretty quick. Straight to the point eh?"

"I'm sorry, I assumed you'd want to get changed someplace so we could hang out."

"I don't follow."

"You know, meet at a hotel or my place, change into you then we could hangout."

"I don't change, Dave."

"You don't?"

"No."

"This is great! How about a drink somewhere?"

"Sounds good. I don't know the town yet so if you could recommend I can meet you there."

"I know a place called Chloe's. It's on Haywood St.. How about around seven?"

"Seven sounds great, I'll see you then."

David is the most socially awkward person I ever met but once we settled into a cozy corner of the bar and we were alone he seemed to relax a little bit.

He told me many times how beautiful I am, how sexy I am and he couldn't believe he asked me to meet him at a gay bar. He seemed to scold himself when he said that last part saying of all places.

I told him anywhere was fine with me and that I had all night we could go anywhere later. I really liked how he kept looking me over. I was wearing the cute yellow summer mini dress and white wedges. Underneath I wore a white lace thong and a strapless bra as this dress can easily go off the shoulder. I added a black velvet choker and big silver hoop earrings along with some silver bracelets. My hair is up in a high ponytail and I am feeling extremely sexy and horny especially with this plug inside me.

David is a very tall guy and built solid. His black t shirt looks painted on his well defined torso, his legs are like tree trunks and his hands a huge. His wild black hair doesn't have a style except maybe controlled messy yet it fits his sharply chiseled handsome features. But he's so shy and awkward I'm starting to see what he meant by him not being able to talk to women very well.

We had a couple drinks then I asked if he'd like to go someplace else and he said sure. So we left the bar and started walking around since we were downtown.

As we walked I took the initiative and his arm as though we were a couple just out for an evening stroll. At first this seemed to catch David off guard but then to my delight he began to relax. He even reached down and took my hand in his.

We stopped in one restaurant that was nearly empty and had ourselves another cocktail. We sat at the end of the bar like two lovers talking quietly and cozying up to each other.

David told me more about his work. He's an architect with a very small yet very prestigious firm and his job is to edit all the drafts submitted by the designers. His company works on everything from small jobs to large scale architectural engineering projects.

He told me the best part for him is he gets to work from home and at his pace.

"Would you like to see my place? It's very close by." He asked in a somewhat timid manner as though this was a crazy idea.

"I'd like that." I said as I was getting extremely horny and wanted him. And I knew I would have to make the first move.

His place was very close by, in walking distance two blocks and then we entered a bougie apartment building. The main foyer is all marble and mirrors and a doorman stood behind a tall desk greeting us, "good evening Mr. Hampton, Miss." he says smiling at me. I believe he also gave David a look of approval.

"Hi Donald."

"Have a good evening sir." He says as we walk through to the elevators.

David lives on the fifth floor, the top and there are no other apartments up there, just his. As we walk in to vast living room the entire back wall is all glass with a patio.

"Holy crap! Look at that view." I say as I stroll out towards the huge sliding glass doors.

"Wine?" He asks from behind me.

"Please."

"Make yourself at home, Jennifer. I'll be right there."

I was on the patio when David came out with two glasses of red wine. "You're rich." I state.

"Part old money part mine."

"You mean like old southern money? Because you don't sound like you're from the south."

"I'm not my family is."

"So why the interest in someone like me? You could have anyone you desire."

"It's not really true that money can buy anything, Jennifer. And meeting a girl like you has been a dream of mine ever since I saw this one gamer online last year."

"A gamer?"

He pulled out his phone and showed me several pictures of what looked like a very pretty girl with long brown hair and very feminine features. He said this is really a guy. And ever since he's seen her he's wanted to meet someone like her. Being bisexual he thought this would be the best of both worlds. But he hadn't met anyone close to his online crush until he saw me last week.

"He's pretty."

"I think you're prettier."

He's standing next to me and I lean in against him and he puts an arm around me. He seems more relaxed, calmer than when we were out.

I turn and face him and have to crane my neck as he's so tall. He gets the idea and leans down as we kiss. David is a great kisser and holds me close as our tongues begin to dance and intertwine.

I can feel his manhood on my belly and it's fairly hard. With this plug still in he has no idea how badly I want him so I break our kiss and lead him back into the apartment.

He lets me lead him back to the huge sectional couch where I playfully push him down then straddle his lap continuing our kiss deep and sensually. It's hard not to get into the mood with his hands all over me and this amazing kiss.

I grind on his crotch feeling his cock is hard and I want this now and I know I have to take the initiative.

I slide over so I'm next to him and begin unbuckling his belt. He helps me get him out of his pants and I take over.

I lean down and rub my cheek over his meat while looking up at him for his reaction. His smile and his hand in my hair shows his approval. I place little kisses on his hard cock through his boxers feeling him twitch as he moans a little. Then I suck the side of his cock slow and sensually moving down the shaft to his balls burying my face in his boxers gently.

I've seen all this done in videos on my phone and it really turned me on, made me want to do this to a man.

I work my lips back up his shaft gently squeezing his meat with one hand while I also begin pulling down his boxers.

When the tip of his cock appears I lay my head on his lap, kiss the tip sweetly, lick around the rim and he lets out a long low gasp. My lips take the head of his cock as I begin to suck slowly while looking at him.

When I finally have his boxers down and out of the way I take a few inches in my mouth and begin slowly, methodically sucking him as he moans and runs a hand through my hair.

As I get his boxer's further down I realize he's way bigger than I could've imagined. My fingers barely wrap around the girth and even as intimidating as it appears I'm excited and so turned on by his size.

I lift his cock straight up and go down even more as my lips and tongue savor every inch.

"Ohh man this so great." He says as his breathing is heavier and more labored.

I get into a nice rhythm of stroking and sucking all I can take in my mouth, my saliva making him slicker and easier to stroke. At times I would break from sucking and glide my wet lips down the sides of his shaft to his balls, licking and sucking those before licking his long fat cock back to the tip.

I can't say how long I did this but it seemed forever and I believe I could've gone on and on as I really got into his big meat in my mouth.

But then, without even realizing it I whispered this question to him, "will you be my first?"

"Are you sure, Jennifer?"

I nod with an innocent look on my face while I kiss his cock.

"absolutely." He says helping me up off the couch then leading me down a long tiled hallway to a huge bedroom.

The bed is enormous and against the wall as we walk in facing another wall that's pretty much all window.

We kiss again and again, our tongues slowly dancing in each others mouths and I moan as his hands grope and squeeze my ass.

He lays back on the bed with me on top and says in between kisses it's better for me as I'm a virgin to be on top the first time.

As I straddle him I pull my dress up over my shoulders and off and to this day I'll never forget that look on his face as he takes me all in.

"Damn Jennifer, you have the hottest little body."

I lean in and we kiss deeply again as I am totally his now. Whatever he wants I would do no questions asked.

We move all over the bed until we are at the headboard and he reaches over to the nightstand. He gets a tube of gel and tells me to put some on him and myself so that it will help.

Before I do that I pull my panties to the side and reach back there removing the plug.

His eyes widen and smile crosses his features when he realizes what I'm doing. I squint and grimace a little as it slides out and then I show David what I did.

"Nice, very hot baby."

Once he's lubed up and I've applied it to my entrance he tells me to take my time as I begin to lean back on his pole.

I feel the head slide between my butt cheeks but it's not in the right spot so I reach around and guide the head to my entrance.

As I begin to lean back onto him I feel the intense pressure stretching my hole in a slight agonizing sensation. In my mind the pain will subside momentarily like the plug did but this was different on so many levels! As he pushed in deeper I had to catch my breath and I squealed in pain.

"Slow baby, I'm sorry."

I nod biting on my lip as I held fast for a long moment then I pushed down again and the pain returned but not as bad. By now I'm determined to lose my virginity and it's definitely happening however I never imagined it would be with such a huge cock.

Charles has a decent size one and that probably would've been less painful yet here I am straddling David's big dick and it's starting to go deeper and deeper inside me.

I feel as though I'm splitting apart right down the middle and I should be screaming out in pain yet it's not as painful anymore. I reach behind me to gauge how much I've taken and unbelievably it's half maybe more.

My breathing is a shallow as I push down more and I moan with pleasure as I get more of his shaft deep inside me. The feeling of him filling me is sensational and exhilarating taking my breath away.

"Oh wow Jennifer you're so tight."

I giggle softly, "you're too big."

"Really? Well I'm all the way in now."

That surprised me as I felt like I had a long way to go yet I realized I was sitting on his lap now with his shaft all the way up inside me and zero pain, just the sensation of having my ass filled.