Fool of Love (4)

Heythere dudes and dudettes.

I am back again with another caption
Another entry into the Fool of Love series that was commissioned by eigth88.

Andrew doubts Alissa loves him, but she shows him that she loves him very much in fact.
Then again her shoving him love does not look like a good thin in the end...

I hope you all enjoy, and until the next time stay happy and healthy.

-----
Alissa felt like the happiest woman on earth right now, and who could blame her?
After all how many women can claim to have a boyfriend, fiancee or husband that would do nearly EVERYTHING for them, going as far as to dress like a woman and going on dates with another man?
'Not many women can claim to have such a dedicated partner' Alissa thought to herself with a smile as she made her way home from work, ready to share the good news with her fiancee Andrew.
Sadly not everything was all sunshine and roses, but Alissa prided herself in her ability to be able to have Andrew go along with what she has planned.

"A-Alissa, do you still find me attractive?" Andrew said to Alissa shortly after she walked trough the front door, and the comment immediately made her eyes go wide.
"What?! Of course I do honey! Why would you ever think otherwise?!" she answered his question, her voice both sweet and appalled that her fiancee would even think such a thing.
"Well, I just thought with how I look, and the d-da-dates I have gone to and the things I did that you would not love me anymore..." Andrew stammered out, unable to look Alissa in the eyes.
'Oh, so THAT is what this is all about. Well, I know a way to show him how much I love him' the woman in question thought before throwing herself at Andrew and forcing him into a deep kiss.

Alissa then hugged him to her tightly, deepening the kiss while the sensation of his sensitive chest rubbing against her forcing him to moan, which only increased when she began to fondle his ass.
After nearly a minute the two lovers separated, greedily huffing in air.
"Andrew, how can I NOT love you after all you do for me? It is quite the opposite, everything you did up to now only made me love you more. After all why would I have requested more-home office at work today if I did not want to spend as much time as possible with you?"
This made Andrew's eyes widen in shock and joy, with his mouth forming into a big smile.
"Besides what sane woman would not love that booty of yours" she continued with a teasing smirk before fondling her fiancee's ass harder, making him let out more moans.

"D-Does that mean y-you let me out of my c-cage so I can cum?" he mewled, his brain nearly getting fried as his lover continued to knead his cheeks like dough.
"Sorry, I can't do that" Alissa said, her eyes gazing apologetically into his to reassure him.
"After all this is still your training, and we don't want to lose all the progress we made, right?"
Hearing that made Andrew frown a bit, but he knew what he got himself into when he decided he wanted to marry Alissa, so he reluctantly agreed to her point.
"Oh, but don't worry honey, I will make sure to give you all the attention you can want instead! That said, how about we move on to buttplugs?"

And so 2 weeks went by where Andrew got teased relentlessly thanks to Alissa working from home.
Each and every day was filled to the brim with make-out sessions, her kneading his ass for hours and sometimes even spanking it, and of course every day his ass was filled with a vibrating buttplug that randomly started to pulse, going from a barely noticeable vibration to a jackhammer.
During those 2 weeks Andrew tried his best to stay strong, trying to fight the horniness Alissa's actions caused him alongside the libido boosters he did not know he was taking.
But every man, no matter how strong, has a breaking point, and after 2 weeks and after another heavy make-out session with the buttplug on max, Andrew reached his.

"P-please Alissa, I c-can't take this anymore! Please let me cum!" Andrew pleaded with small tears in his eyes after him and the woman in question finished their newest make-out session.
"You know I can't do that Andrew, it would ruin t-" Alissa started, but was quickly interrupted.
"GOD, PLEASE LET ME CUM!" he nearly shouted, starting to rub his caged crotch against Alissa's leg, humping it like a dog to try and get rid of the horniness he feels.
'Maybe I have overdone the teasing a bit' Alissa thought when she saw how her fiancee behaved.
'But this just means we can take the next step earlier' she continued, never thinking less of Andrew, after all she knew what she was doing to him, and his reaction was reasonable.

"Well, there is something that I can do to help you, bu-" "DO IT!" the horny guy once again interrupted with a shout, making Alissa give him a look.
"But after I do this you will have to d-" "I DON'T CARE, I WILL DO ANYTHING, JUST HELP ME CUM!"
Hearing that Alissa gave Andrew one last look, before giving him a small smile and a nod.
"Okay then, go to the bedroom and wait for me, I will be there shor-" she started, but before she could finish her sentence Andrew was already sprinting up the stairs.
'Well, this will be fun' was the only thing that ran through her mind as she began to smile more.

After a few minutes Alissa entered the bedroom, and saw Andrew on the bed, waiting expectantly in his tight black outfit, and Alissa had to stifle a giggle at how eager he looked.
"Okay Andrew. Get on all fours, stick your ass out, and don't look back!" she commanded, and normally he would question why, but Andrew was way too horny to care, so he did as told.
Once his backside was facing her Alissa stepped forward and slowly pulled down Andrew's trousers before grabbing the shiny anal plug and removing it with a wet plop, making Andrew shudder.
"God yes" he moaned as he felt the plug leave his ass. "Now please get rid of the cage and let me cum!" he continued, throwing his ass back more so Alissa has easier access to the cage.

But the woman in question never planned to unlock her fiancee, it would ruin all the training they did after all, so instead she pulled the strap-on out of her pants and covered it in lube.
"Sorry, I still can't unlock you, honey, but as promised I will help you to cum" she said to him, and before he could retort she started to insert the tip of the strap-on.
After a few seconds it plopped into Andrew's ass, thanking the plug for widening him, before she started to lean forwards, burying nearly all 5 inches into him in one go.

"AHHHH!" Andrew moaned out in reply, and before he knew it his fiancee was pounding in and out of his ass, with her hands either smacking his cheeks or groping his chest and nipples.
"Oh, you like that, don't you?" Alissa growled into his ear, feeling how he started to buck his hip back into her as she hit his prostate over and over again.
"N-No, I don't!" he weakly replied in a voice that would make everybody doubt that statement.
"Oh, you should not lie, honey!" Alissa said back, giving his ass a harsh smack as punishment that only made Andrew moan louder in return.
"But I am glad you like it, after all this piece of plastic will be a real cock soon!"
"W-what? What do you meAAAAA!" he started to question before he started to shout as after weeks of suffering blue balls he finally came, getting the biggest orgasm of his life.

After that Andrew simply collapsed onto the bed, huffing and puffing as Alissa collected his cum.
"Well, you said you will do anything for me to help you out. And I want you to take the next step" she just said, enjoying how her exhausted fiancee was lying below her.
"A woman will only cum if she gets fucked properly after all, and since I can be sure you can cum while caged the only way for you to get off will be by taking a real dick up your ass! So coming next week your dates can expect some anal fun, of course only if you want to cum."
Hearing this made Andrew pale, because through his mind was hazy he knew what she implied.
But he did not have much time to dwell on this topic as he felt Alissa start to move, once again pistoning the strap-on in and out of his ass.
"But for now you can have some fun with the plastic fake. I hope you still have some stamina in you, because I am quite far from being done with you, honey!"