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                 K R I S T E N' S    C O L L E C T I O N
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Should Have Let the Past Stay Buried
by Lisa Raye (address withheld)

***

A man digs into his wife's past due to jealousy. His 
impotency and other circumstances cause him to suffer 
humiliation and feminization as his wife's past lover 
steps back into her life. (MMF, nc, bi, tg, oral, anal, 
intr, size, huml, cuck)

***

This is not an easy story to tell. I tell this story in 
hopes that others do not make the same mistakes I have 
made. I had a wonderful life with a great wife until I 
decided to search deeper into my wife’s past. I should 
start by telling you about her. Her name is Lisa. She 
and I were married just after I returned home from 
college. We had not known each other in school even 
though we went to the same high school with her 
graduating one year earlier. She was a late bloomer. 
She is 5’6”and weighs 120 pounds with very nice 
features. She was a tomboy and slightly overweight in 
school. 

We met just after I came home. I have a doctorate in 
education and teach online college courses from my 
home. My wife does not work. We fell in love quick once 
we found each other. After only 3 months of dating, I 
popped the question. The wedding was set for just 6 
months later. I know this may seem hard to believe but 
I was still a virgin when we got married. It was 
probably because I was somewhat of a nerd. 

Lisa was amazed when I shared this with her just one 
month before our wedding. Once she got over her 
astonishment, she became outwardly concerned. As she 
began to speak, I knew that she was about to tell me 
that she was not a virgin. I was right. She shared that 
she did not want me to find this out on our wedding 
night. 

I remember that I paused for a moment and then told her 
that it was okay. I did ask her if her past was 
something that I should be concerned about or if I 
would have to come in contact with many of her past 
partners. She shared that she had only experienced one 
sexual encounter with a man she didn’t even like and 
that it was the biggest mistake of her life. With tears 
in her eyes she said that the man had seduced her in a 
time that she was vulnerable. She added that the man 
now lived out of the country. I was glad that she 
looked at her past as a mistake. My ego told me that it 
must have not been great or something that I would have 
to worry about. We had been married about 2 years when 
events would occur that would change my life.

Our marriage was very good. Our sex life was good. I am 
5’9” tall. I had been able to pleasure her nicely in 
bed, according to her. Our sessions always lasted at 
least 15 minutes before I would have an orgasm. I did 
notice that Lisa did not orgasm during our intercourse. 
She worked hard to grind herself on me in efforts to 
reach orgasm. However, I always finished before she 
could climax. 

She would then flip on top at this time and continue to 
grind on me until my penis had shrank from its 5” 
erection. I soon learned how to place my fingers 
between us and let her continue to grind on my hand 
until she finished. I loved watching her reach orgasm 
as she bit her bottom lip. Life was very good. That was 
until I contracted diabetes. The sickness was hard on 
me. 

Eventually, I was able to control the sugar levels, but 
the disorder had taken its toll on my ability to gain 
an erection. This was before the days of Viagra. And 
the cost of a penile implant was too much and not 
covered by insurance. I was devastated. I became 
depressed at not being able to make love to my wife. 
She was supportive but I knew she was also devastated 
at not having intercourse. I became determined to 
pleasure her sexually. 

I made it a nightly routine of giving her oral sex. She 
resisted at first but learned to enjoy it. I tried to 
introduce dildos into our routine but Lisa was not into 
this at all and asked that I not use them anymore. 
After a few months, I could tell that Lisa was becoming 
depressed at not having intercourse. Finally, I 
swallowed my pride and jealousy and told her that I 
knew she needed to feel like a woman and have sex. 

I told her that if she wanted to she could take a 
lover. I told her that I would hate it but that her 
happiness was most important. I told her that my only 
request was that she practice safe sex with condoms for 
safety reasons. The truth was that I also hated the 
idea of another man’s cum being inside her. Lisa became 
angry and said that she would never think of having sex 
with any more men. She said that the feeling of another 
man using and owning her was overwhelming and just not 
an option. So life went on. 

One weekly activity in our life was to visit Lisa’s 
mother. She lived in an apartment in town. After about 
a year into our marriage, Lisa’s mother became ill. She 
was an older lady when she had her kids. She needed to 
be put in a home or live with someone. Lisa and I did 
not have an extra room, so her mother moved in with 
Lisa’s sister, Rose, who lived in a large apartment in 
a rough area in town. Rose’s apartment was huge and she 
ran a beauty salon out of the apartment. 

Lisa was not happy to see her mother move in with her 
sister. Rose and Lisa did not get along very well. I 
could never point to anything in particular, but we 
only saw Rose around the holidays. Part of the reason 
for their bad relationship was due to the fact that 
Rose was the “wild” child of the family. She had run 
away a young age and married a black man she had met at 
the mall. Her husband, Willie, was an okay guy but a 
little cocky and not so friendly. After Lisa’s mom 
moved in with Rose, we began to make our weekly visits 
there. 

Our visits did not last as long. Some of this was due 
to the fact that Rose was a smoker and the longer we 
stayed the worse we smelled of smoke when we left. Lisa 
and Rose barely spoke on most visits. That was until 
one Sunday afternoon when we were there on our weekly 
visit. Rose struck up a conversation with Lisa as we 
were about to leave and proceeded to ask my wife to 
guess who moved into the apartment on the third floor 
of the building. 

She then told how Willie’s brother, Danny, had finished 
working for a company in Iraq and had moved back home. 
Lisa turned pale and became very quiet before finally 
shrugging off the news and telling everyone goodbye. As 
we opened the door to leave, we were met by a huge 
black man. He was about 6’5” tall and very muscular. I 
was shocked to hear him say hello to my wife by name as 
she walked by and pulled me along. 

The way he said hello left me with a terrible feeling 
in my gut. On our ride home I finally broke the silence 
with the obvious question that I wish I never asked. I 
asked her if Danny had been her ex-boyfriend that was 
out of the country. She paused for a long time and 
finally confirmed that he was as she began to sob. 
Again, it was silent for a long time. I was shocked. 
Not just that my wife had had sex with a black man. 

I just could not see a scenario where my wife would 
have fallen for that kind of guy. This came from 
hearing the way she hated Rose’s choice in men and the 
fact that she was attracted to me. 

I wish I would have dropped it, but I continued to ask 
her questions. I asked her if this was the root problem 
behind her and Rose’s bad relationship. She confirmed 
that it was. I then asked her how Rose got in the 
middle of it. She paused and then finally began to 
recount how she tried to keep Rose as a close sister 
even after Rose moved out. She said that she would 
occasionally drive over and see Rose or meet her at 
their mother’s house. She said that she always confided 
in Rose. 

Lisa said that one day, after she had been out of high 
school for a couple of years, she had a bad break-up 
with her boyfriend at the time. She said that she was 
heartbroken and went to Rose’s for support. They 
discussed how the boy broke up with her because she 
would not have sex with him. Lisa recounted how Rose 
was amused to find out that Lisa was still a virgin. 
Lisa listened to her sister and trusted her. Rose told 
Lisa that she could help her. She told her to come back 
to her apartment on Friday night and she would help her 
out. Lisa proceeded to tell me what happened when she 
arrived that Friday. Rose told her that she was going 
to take Lisa to a party. 

She said that if she was brave enough, she could go to 
the party for 20 minutes. If she did not meet a man 
that she wanted to have one round of meaningless sex 
with, she could leave. Rose’s only rules were that Lisa 
let Rose fix her up for the party and that Lisa commit 
to the 20 minute minimum before leaving. Lisa told me 
that she wanted to back out but she felt very lonely at 
the time and she didn’t want to seem unappreciative to 
her sister. 

She let Rose begin the make-over there in the salon. 
Lisa told me that one hour later Rose let her out of 
the chair and handed her a party dress to put on with 
shoes and all. Lisa, Willie and Rose then left for the 
party. It was then that Rose told her that the party 
was in Danny’s apartment. She also told Lisa that her 
new purse contained a few items she might need. One was 
cigarettes. Rose told her that men loved to see women 
smoke. 

She said that this would also be her way of telling 
time. She told her that each cigarette would take about 
5 minutes to smoke. She said that 4 cigarettes had to 
be smoked before they would leave. Lisa told me that 
she had tried smoking with her sister before she moved 
out. She agreed to give it a try. Lisa then told me 
that she must have been very naïve to be going to a 
party in a black neighborhood wearing a fancy dress and 
high heels. 

Once they arrived, Lisa was more shocked to find that 
Danny was the only one there. Rose was trying to fix 
them up. Lisa immediately tried to back out but Rose 
became angry and insisted that she at least stay for 20 
minutes so that Danny’s feelings would not be hurt. 
Lisa said that she immediately lit the first long white 
cigarette to start the clock. As they sat and talked, 
Danny put on some music. Lisa said that he asked her to 
dance just as the first cigarette was put out in the 
ashtray. She agreed to one dance. 

She said that Danny started out being very nice. He was 
polite and seemed to agree that Rose should not have 
set her up like she had. She went on to tell me that 
after 3 cigarettes and 3 drinks; she was feeling a 
little light headed. She said that she was not used to 
doing either. She told me that during one more slow 
dance, she became weak kneed and Danny began to hold 
her tighter as they danced. 

It was then that he danced her into his bedroom. She 
said she tried to resist, but Danny was persistent. He 
began to tell her that she needed to lose her cherry 
and that she would be a new woman if she would give in. 
I sat in awe as she shared this story almost like she 
needed to confess it to someone. She skipped the 
details and ended the story by saying that the drinks, 
the smoking, the incense burning and her current state 
of mind all contributed to Danny seducing her into sex. 
She then said that when it was over, she walked back to 
Rose’s apartment. 

Rose was waiting for her with a huge smile on her face. 
She said that they had a huge fight as Lisa was now 
feeling guilty and used. She said she still remembered 
Rose acting like she was excited that she had set Lisa 
up to lose her cherry. Rose told her that no one could 
resist a huge black man when the mood was set just 
right. She told Lisa that the make-up, dress, heels, 
cigarettes were all part of the plan and that she had 
no choice but to spread her legs for Danny. 

She went on to tell Lisa that Danny would forever own 
Lisa in a special way. Lisa told me that she cried 
herself to sleep on Rose’s couch since she did not want 
to leave in that neighborhood that late. I could tell 
that the event was traumatic for my wife, so I hugged 
her. 

I tried to remain quiet. In my mind I was feeling very 
jealous and very threatened. However, I was full of 
questions in my mind. How could I have competed 
sexually with this huge man? How long did their sex 
session last? What else did Lisa do with him that 
night? I was full of questions. I still tried to remain 
silent. I wanted it to all go away. However, I once 
again could not keep my mouth shut. I broke the silence 
with one question I had to know the answer to. 

I asked Lisa why she had not told me that her sex 
partner was a member of her sister’s family when we had 
discussed it years earlier. She explained that she 
thought Danny had moved away forever and that she never 
anticipated having to go to Rose’s house every week due 
to her mother living there. She said she was sorry. I 
continued to hug her but wondered in my mind if I would 
have been okay with knowing this before we were 
married. I reasoned that I would have still married 
her. 

Then I began to contemplate the statement Lisa had mad 
to me that she would not give herself sexually to any 
“more” men. I was sickened by the thought of it, but 
began to consider whether Lisa might need to turn to 
Danny to fill the sexual void in her life due to my 
impotency. 

Life went on. Each week we made our visit to Lisa’s mom 
and each week Rose took great delight in having Danny 
there to make Lisa and I feel uncomfortable. Danny was 
a jerk. He always made inappropriate statements and 
remarks about Lisa looking good or how he would love to 
catch up on old times. Finally, one day after leaving 
there to come back home, I asked Lisa why she put up 
with his comments. She said that she was not going miss 
visiting her mother so she really didn’t have a choice. 

I again began to stick my nose in where it didn’t 
belong. I told her that she needed to stop feeling 
guilty about what had happened and she should show 
strength to Rose and Danny. I said that she should tell 
them that it was just a big mistake and that she had 
learned from it. I was trying to get my wife to take 
responsibility for her actions and say that she had 
made a bad choice rather than blame what had happened 
on her being tricked by her sister or seduced by a man. 
I wanted her to admit that she could have said no but 
chose not to. She paused for a moment and said that she 
wasn’t sure she could have said no. I corrected her and 
said that no amount of booze, sexy clothes, cigarettes 
or anything else can make you do something you don’t 
want to do. She finally agreed. 

I told her that we needed to act like nothing ever 
happened and try to just be friends with her sister and 
her family. I then surprised her by telling her that if 
she wished to take Danny as an occasional lover due to 
my impotency, I would understand. She stared at me in 
shock. I reminded her that this would involve her 
sleeping with a man she had already been with and would 
not go against her earlier promise of not sleeping with 
any new men. I told her that I would still always share 
oral sex with her. Lisa said that I didn’t know what I 
was saying and that sex with Danny was out of the 
question. I dropped it. 

The next Sunday we tried being friendlier to Rose, 
Willie and Danny. They seemed a little surprised. 
During the visit, I got Rose off in the kitchen alone. 
I told her about my situation with by diabetes and my 
sex life. I told her that I wanted Lisa to get to have 
sex. I also told her that I thought Danny was the only 
option due to the fact that Lisa stated she would not 
sleep in any new men. Rose stared at me in shock. I 
told her that my and Lisa’s marriage was great and I 
felt confident that Lisa would not fall in love with 
Danny or leave me. It would be sex only. 

I told her that Lisa would never agree to it up front. 
I said that we might have to fix it where we surprise 
Lisa and put her in a position of being alone with 
Danny. Rose thought for a while as she smoked her 
cigarette. She finally spoke by saying that she might 
have a plan. First, she said that she wanted to know 
what was in it for her. I asked what she meant. She 
said that Danny and Lisa were getting sex and I was 
getting my wife pleasured. She said that she wanted 
something out of the deal. 

I asked what she wanted. She told me that her husband 
was well-endowed. She told me that their sex life was 
great except for the fact that Willie loved to receive 
oral sex and her mouth was too small to pleasure him. 
My stomach began to hurt as she said that if I would 
give her husband a blowjob, she would set up the rest. 
I refused immediately. She began to reason with me that 
it was just a blowjob and that I would really be doing 
her a favor. 

The thought disgusted me and I told her so. She said 
that I should think of it as making my wife happy. I 
told her I would try but that I might not be able to go 
through with it. She then told me to wait there for a 
minute. She returned with Danny. She told me that she 
had told Danny the situation but if I wanted this to 
happen I needed to ask him the big question myself. I 
swallowed hard as I looked up at this huge man. 

I finally asked him if he would be willing to pleasure 
my wife sexually from time to time. He made it harder 
and clarified it by asking if I wanted him to fuck my 
wife. I nodded and hung my head. He said that he would. 
I added a couple of conditions. I told him that he 
could not force her or hurt her. I also added that he 
had to wear a condom. Lisa was on the pill due to other 
reasons, but I did not want the risk of STDs. Plus the 
thought of his cum inside her somehow made it worse to 
me since my only sex with her was oral. He agreed to 
both of these demands. 

Rose and I rejoined the others. Soon after this, Rose 
announced that she was having a costume party for 
Halloween in a couple of weeks. She invited Lisa and me 
to come. Lisa said she was not interested. I told her 
that this would be a great way for us to become better 
friends with her sister and her family so Lisa finally 
agreed to come. Rose then announced that the costumes 
that each would wear would be drawn out of a hat. She 
said we would need six costumes ideas as she would 
invite a girl that lived in the building named Sue. 
Rose began writing down costume ideas on slips of paper 
and asked for input. She called out “Pimp” and then 
“Cowboy.” 

Willie then called out “Hooker.” This was followed by 
Lisa saying “Nurse.” Rose said that someone would have 
to be a “French Maid.” Needing one more male costume, 
Lisa mentioned “Construction Worker.” Rose folded up 
the slips of paper and put them “all” into a hat. I 
told her she had made a mistake. She told me that it 
would be fun if some had to come as the opposite sex. 

Lisa was smiling at my discomfort and the others did 
not seem to mind so I went along even though I was a 
little nervous. Rose said she was drawing for Sue 
first. She got “Nurse.” Next she went over to Willie. 
He got the one I wanted, “Cowboy.” She then went to 
Danny. He drew my second choice, “Construction Worker.” 
My stomach began to hurt. Lisa drew next and got 
“French Maid.” She looked nervous but decided it was 
all for fun. 

It was down to me and Rose. She said I could draw 
first. I had a 50/50 shot at pimp. I drew and everyone 
burst out laughing when I stared silently at my paper, 
“Hooker.” I never said it out loud. Rose took hers and 
triumphantly confirmed that she was “Pimp.” 

I turned to Lisa and told her that I could not do this. 
Lisa threw my words back at me that this was for fun 
and that we should go along. She added that I had 
always wanted her to dress provocatively for me so now 
I could see what it was like. I told her that I didn’t 
know how to dress that way. Rose quickly volunteered to 
help Lisa and I get ready for the party. She said that 
she would take care of everything and that we just 
needed to show up early the night of the party. I 
agreed to go along knowing that this was all for Lisa 
anyway. 

The day of the party finally arrived. Lisa had been 
riding me for two weeks about my costume. I was glad to 
see her at least not totally depressed for a change. We 
left early for the party. Once at Rose’s, we saw that 
she had decorated a lot for Halloween. She told me to 
go to her bathroom and she would be there shortly. She 
led Lisa into the beauty salon. Rose came in and told 
me that I would need to take a bath and shave my face, 
legs, chest and arms. When I protested, she reminded me 
that this was my idea and to go along. 

I then asked her why she arranged for me to be a hooker 
for this party. I knew she had fixed the drawing 
somehow. She said that she knew her husband would want 
me dolled up to when giving the blowjob as he was not 
gay either. I reminded her that I didn’t know if I 
could go through with it. She told me that I had better 
try hard after all she had gone through. I proceeded to 
take a bath. I did as requested. I felt weird without 
any hair on my body except for my head and pubic area. 
Rose returned and said that she had fixed Lisa’s hair 
and make-up and she was now getting dressed. 

She did not seem fazed at seeing me naked. She seemed 
to be staring at my cock which was now shriveled to 
near nothing due to the diabetes. She took a pair of 
scissors and a razor and proceeded to trim and shave my 
pubic area into a small triangular bush that would fit 
under bikini styled panties. She then led me to her 
bedroom where my costume was laid out on the bed. She 
told me to lie on my back on the bed as she was doing 
something with a cone shaped piece of rubber near her 
dresser. She came near me and went to place the rubber 
object on my chest. I stopped her. She informed me that 
this was just a fake breast. She said the glue was not 
permanent. I let her continue. 

Soon the glue had set and I had two size D breasts with 
big nipples. Standing, the breast felt heavy and moved 
very realistically. She strapped me into a black corset 
that included a bra that pushed my breasts up into 
cleavage. She tightened the strings in the back very 
tight, giving me a curvy form. She then helped me pull 
black stockings up my legs and attach them to garters 
on the bottom of the corset, being sure to keep the 
seams straight in back. 

Next came a pair of matching silk panties. Rose had me 
tuck my penis down between by legs. I could not believe 
how uncomfortable these clothes were. I stepped into 
the leather mini-dress. I put my arms through the short 
sleeves. Rose zipped it up in back which snugged it up 
and closed the high collar around my neck. The dress 
hem barely covered my stocking tops. Lastly, Rose had 
me step into the 5 inch black heels and fastened the 
ankle straps in place. 

Rose then led me to the beauty parlor. Lisa was sitting 
reading a magazine. She was smoking one of Rose’s long 
menthol Virginia Slims. Rose told me that Lisa was 
nervous and they thought the cigarette might calm her 
nerves. Lisa looked so slutty but sexy sitting there 
dressed as a French Maid smoking. Lisa giggled watching 
me trying to walk in my costume. 

I was barely able to walk without falling. I sat in one 
of chairs and Rose covered me with a bright pink 
plastic cape. She then began applying the make-up. 
There was so much. She used liquid foundation, powder 
foundation, blush, eye shadow, eye liner, mascara, lip 
liner, and lipstick. She spent most of the time on my 
eyes. My face felt heavy. 

Rose then told me that she was going to use a wig 
instead of fixing my own hair. She placed a blonde wig 
on me and attached it with pins to my own hair. The 
last thing would be my nails. She used glue on tips 
that were a full inch past my regular nails. She then 
painted them a bright red that she said matched my 
lips. 

I was then allowed to look in the mirror. I became 
scared. I looked just like a hooker. I was not bad 
looking. I didn’t like the way it made me feel. 
Thinking about Lisa being with Danny and me actually 
sucking a cock finally hit me. I had to sit down to 
avoid getting sick or fainting. Lisa offered me a 
cigarette, saying that it had calmed her down some. I 
held it as she lit it. 

After a few puffs, I could tell it did seem to calm me. 
Lisa said that this could be a fun evening and thanked 
me for going along. We sat together for a while as Rose 
went to get ready. She finally came back looking just 
like a pimp. She had the suit and the big furry hat. 
Soon the doorbell rang and Danny and Sue were arriving. 
Willie came into the room next.

Every costume was well done. We had some snacks and 
eventually Willie asked Rose to dance. This was 
followed by Danny asking my wife to dance. She 
hesitated but I told her to go ahead. They were talking 
as they danced but I could not hear them. After the 
first dance, I asked Lisa to dance. She agreed. I am 
sure we looked odd; a hooker and a French Maid dancing 
together. She told me that Danny was glad to see that 
we were not holding a grudge against him and Rose 
anymore. 

END

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
This story was written as an adult fantasy. The author
does not condone the described behavior in real life.

~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
Kristen's collection - Directory 61